Pub Date : 2024-01-26DOI: 10.2174/0115701786277281231228093405
Lichao Zhang, Xueting Wang, Kang Xiao, Liang Kong
: N4-methylcytosine (4mC) is one of the most important epigenetic modifications, which plays a significant role in biological progress and helps explain biological functions. Although biological experiments can identify potential 4mC sites, they are limited due to the experimental environment and labor-intensive process. Therefore, it is crucial to construct a computational model to identify the 4mC sites. Some computational methods have been proposed to identify the 4mC sites, but some problems should not be ignored, such as those presented as follows: (1) a more accurate algorithm is required to improve the prediction, especially for Matthew’s correlation coefficient (MCC); (2) easier method is needed for clinical research to design medicine or treat disease. Considering these aspects, an effective algorithm using comprehensible encoding in multiple species was proposed in this study. Since nucleotide arrangement and its property information could reflect the sequence structure and function, several feature vectors have been developed based on nucleotide energy information, trinucleotide energy information, and nucleotide chemical property information. Besides, feature effect has been analyzed to select the optimal feature vectors for multiple species. Finally, the optimal feature vectors were inputted into the CatBoost algorithm to construct the identification model. The evaluation results showed that our study obtained the highest MCC, i.e., 2.5%~11.1%, 1.4%~17.8%, 1.1%~7.6%, and 2.3%~18.0% higher than previous models for the A. thaliana, C. elegans, D. melanogaster, and E. coli datasets, respectively. These satisfactory results reflect that the proposed method is available to identify 4mC sites in multiple species, especially for MCC. It could provide a reasonable supplement for biological research.
{"title":"An Effective Algorithm Based on Sequence and Property Information for N4-methylcytosine Identification in Multiple Species","authors":"Lichao Zhang, Xueting Wang, Kang Xiao, Liang Kong","doi":"10.2174/0115701786277281231228093405","DOIUrl":"https://doi.org/10.2174/0115701786277281231228093405","url":null,"abstract":": N4-methylcytosine (4mC) is one of the most important epigenetic modifications, which plays a significant role in biological progress and helps explain biological functions. Although biological experiments can identify potential 4mC sites, they are limited due to the experimental environment and labor-intensive process. Therefore, it is crucial to construct a computational model to identify the 4mC sites. Some computational methods have been proposed to identify the 4mC sites, but some problems should not be ignored, such as those presented as follows: (1) a more accurate algorithm is required to improve the prediction, especially for Matthew’s correlation coefficient (MCC); (2) easier method is needed for clinical research to design medicine or treat disease. Considering these aspects, an effective algorithm using comprehensible encoding in multiple species was proposed in this study. Since nucleotide arrangement and its property information could reflect the sequence structure and function, several feature vectors have been developed based on nucleotide energy information, trinucleotide energy information, and nucleotide chemical property information. Besides, feature effect has been analyzed to select the optimal feature vectors for multiple species. Finally, the optimal feature vectors were inputted into the CatBoost algorithm to construct the identification model. The evaluation results showed that our study obtained the highest MCC, i.e., 2.5%~11.1%, 1.4%~17.8%, 1.1%~7.6%, and 2.3%~18.0% higher than previous models for the A. thaliana, C. elegans, D. melanogaster, and E. coli datasets, respectively. These satisfactory results reflect that the proposed method is available to identify 4mC sites in multiple species, especially for MCC. It could provide a reasonable supplement for biological research.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"18 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139579696","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
: The benzimidazole scaffold is a promising nucleus for developing novel therapeutic agents for ulcer treatment. Its unique chemical structure provides desirable pharmacological properties, such as excellent bioavailability, metabolic stability, and low toxicity, making it an attractive candidate for ulcer treatment. Several benzimidazole derivatives have shown significant anti-ulcer activity in preclinical and clinical studies, acting through multiple pathways, including inhibition of gastric acid secretion, suppression of gastric inflammation, and promotion of mucosal protection. Some benzimidazole derivatives have also demonstrated anti-Helicobacter pylori activity, suggesting their potential for eradicating bacteria associated with ulcer formation. However, challenges such as poor solubility and limited selectivity remain. Various approaches, such as prodrug design and formulation optimization, have been explored to overcome these issues and improve the therapeutic profile of benzimidazole derivatives. Overall, the benzimidazole scaffold holds great promise as a nucleus for developing novel anti-ulcer agents. Further research and optimization efforts are needed to harness its full potential and translate it into effective treatments for ulcers. With continued advancements in medicinal chemistry and drug design, benzimidazole-based compounds may offer new therapeutic options for patients suffering from ulcers and related gastrointestinal disorders. Hence, this review highlights the knowledge about benzimidazole scaffold, the mechanism of ulcer formation, and various benzimidazole derivatives with anti-ulcer activity, which can be further studied in pre-clinical and clinical trials.
{"title":"A Comprehensive Review of the Benzimidazole Scaffold as a Potential Nucleus for Anti-Ulcer Activity","authors":"Kuldeep Singh, Bharat Bhushan, Ajit Kumar Varma, Ravi Shekhar, Rajeev Kumar Sharma, Niladry Sekhar Ghosh, Ekta Pandey, Sunam Saha, Shivendra Kumar, Avinash Kumar Mishra, Mohit Agarwal","doi":"10.2174/0115701786267759231121070546","DOIUrl":"https://doi.org/10.2174/0115701786267759231121070546","url":null,"abstract":": The benzimidazole scaffold is a promising nucleus for developing novel therapeutic agents for ulcer treatment. Its unique chemical structure provides desirable pharmacological properties, such as excellent bioavailability, metabolic stability, and low toxicity, making it an attractive candidate for ulcer treatment. Several benzimidazole derivatives have shown significant anti-ulcer activity in preclinical and clinical studies, acting through multiple pathways, including inhibition of gastric acid secretion, suppression of gastric inflammation, and promotion of mucosal protection. Some benzimidazole derivatives have also demonstrated anti-Helicobacter pylori activity, suggesting their potential for eradicating bacteria associated with ulcer formation. However, challenges such as poor solubility and limited selectivity remain. Various approaches, such as prodrug design and formulation optimization, have been explored to overcome these issues and improve the therapeutic profile of benzimidazole derivatives. Overall, the benzimidazole scaffold holds great promise as a nucleus for developing novel anti-ulcer agents. Further research and optimization efforts are needed to harness its full potential and translate it into effective treatments for ulcers. With continued advancements in medicinal chemistry and drug design, benzimidazole-based compounds may offer new therapeutic options for patients suffering from ulcers and related gastrointestinal disorders. Hence, this review highlights the knowledge about benzimidazole scaffold, the mechanism of ulcer formation, and various benzimidazole derivatives with anti-ulcer activity, which can be further studied in pre-clinical and clinical trials.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"65 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139587149","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Hydrolysis of acetanilides and aminolysis of phenyl and thiophenyl acetates are related reactions since these are processes of nucleophilic substitution on the carbonyl carbon. Current views of chemical reactivity based on the DFT theory rely upon reactivity indices that are descriptors of both the reaction center and the molecule as a whole, and have not been applied to the given processes before. One of such descriptors is an atomic electrostatic potential. The given parameter was calculated by the DFT theory M06/6-311+G (non-specific solvation, MeCN, SMD, and full optimization) for the structures of substituted phenyl acetates XPhO-C(O)Me, acetanilides XPhNHC(O)Me, thiophenyl acetates ZPhSC(=O)Me, and benzyl amines XPhСH2NH2 (X, Z substituents). It has been found that all relationships between the atomic electrostatic potential, the charge on the reaction center in the Hirshfeld scheme, and logK are symbatic. Consequently, in all of the cases, the rate is determined by the nucleophilic attack on the reaction center, with the activity/selectivity relationship being observed. The fact that the reaction rate is limited by the nucleophilic attack of the reagent is not inconsistent with the views of the reaction being concerted, since it is known that such reactions may be quite concerted though not quite synchronous.
{"title":"Atomic Electrostatic Potential as a Descriptor of Aminolysis of Phenyl and Thiophenyl Acetates and Hydrolysis of Acetanilides","authors":"Evgeny Krylov, Lyudmila Virzum, Matvey Gruzdev, Ulyana Chervonova","doi":"10.2174/0115701786287226240104045123","DOIUrl":"https://doi.org/10.2174/0115701786287226240104045123","url":null,"abstract":"Hydrolysis of acetanilides and aminolysis of phenyl and thiophenyl acetates are related reactions since these are processes of nucleophilic substitution on the carbonyl carbon. Current views of chemical reactivity based on the DFT theory rely upon reactivity indices that are descriptors of both the reaction center and the molecule as a whole, and have not been applied to the given processes before. One of such descriptors is an atomic electrostatic potential. The given parameter was calculated by the DFT theory M06/6-311+G (non-specific solvation, MeCN, SMD, and full optimization) for the structures of substituted phenyl acetates XPhO-C(O)Me, acetanilides XPhNHC(O)Me, thiophenyl acetates ZPhSC(=O)Me, and benzyl amines XPhСH2NH2 (X, Z substituents). It has been found that all relationships between the atomic electrostatic potential, the charge on the reaction center in the Hirshfeld scheme, and logK are symbatic. Consequently, in all of the cases, the rate is determined by the nucleophilic attack on the reaction center, with the activity/selectivity relationship being observed. The fact that the reaction rate is limited by the nucleophilic attack of the reagent is not inconsistent with the views of the reaction being concerted, since it is known that such reactions may be quite concerted though not quite synchronous.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"125 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139587148","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-01-25DOI: 10.2174/0115701786278059231122061237
Zahra Zamiraei, Kurosh Rad-Moghadam
: A new bioactive azo dye embedding a thiazolidinone heterocyclic core was designed and synthesized for antibacterial application and colorimetric sensing of cyanide ion (CNˉ) in organic solutions. The structure of the prepared dye was elucidated from its 1H NMR, FT-IR and UV–vis spectral data. It proved to be a fast and sensitive colorogenic sensor for detection of CNˉ. Spectroscopic studies were carried out to investigate the effect of different CNˉ concentrations on the detection efficiency. Moreover, the studies revealed no significant competition or influence of other anions on sensitivity of CNˉ detection by the synthesized dye. A Job's plot indicated a 1:1 stoichiometry of the dye and CNˉ in their colorful complex. Further development of the method for naked-eye detection of CNˉ in low-concentration aqueous solutions was achieved by using the cellulose papers painted with the dye. The as-prepared testing paper allowed CNˉ sensing in concentrations as low as 2 μM. Evaluation of the dye for antibacterial activities using the well diffusion technique displayed that its inhibitory activity is at least as good as and in some cases superior to ampicillin against the bacterial strains employed in the zone assay. In response to CN¯, the dye changes color from yellow to reddish brown that accounts for its significant interactions with CNˉ and affords a naked-eye sensing method without resorting to any spectroscopic instrumentation. background: Cyanide ion is a serious pollutant of industrial wastewaters and is highly toxic for mammals. objective: A new bioactive azo dye embedding a thiazolidinone heterocyclic core was designed and synthesized for antibacterial application and colorimetric sensing of cyanide ions in organic solutions. method: The structures of prepared dyes were confirmed by 1H NMR, FTIR and UV–vis spectroscopies. It was found to be a fast and sensitive colorogenic sensor for detection of CN¯ ions. result: . In response to CN¯ ion, Spectroscopic studies were investigated of the interaction of synthesized dye with cyanide ion in competition with other anions and different concentrations of cyanide ion. The result of the Job's plot indicating that the stoichiometry binding ratios of synthesized dye and CN¯ is 1:1. Further development of the method for naked-eye detection of cyanide ion in low-concentration aquase solutions was achieved by using the cellulose papers painted with the dye. The as-prepared testing paper allowed CN¯ sensing in concentrations of 2 µM. Evaluation of the dye for antibacterial activities using the well diffusion technique displayed that its inhibitory activity is at least as good as and in some cases superior to ampicillin against the bacterial strains employed in the zone assay.
{"title":"A New Bioactive Thiazolidinone-based Azo Dye for Naked-eye Colorimetric Detection of Cyanide Ions","authors":"Zahra Zamiraei, Kurosh Rad-Moghadam","doi":"10.2174/0115701786278059231122061237","DOIUrl":"https://doi.org/10.2174/0115701786278059231122061237","url":null,"abstract":": A new bioactive azo dye embedding a thiazolidinone heterocyclic core was designed and synthesized for antibacterial application and colorimetric sensing of cyanide ion (CNˉ) in organic solutions. The structure of the prepared dye was elucidated from its 1H NMR, FT-IR and UV–vis spectral data. It proved to be a fast and sensitive colorogenic sensor for detection of CNˉ. Spectroscopic studies were carried out to investigate the effect of different CNˉ concentrations on the detection efficiency. Moreover, the studies revealed no significant competition or influence of other anions on sensitivity of CNˉ detection by the synthesized dye. A Job's plot indicated a 1:1 stoichiometry of the dye and CNˉ in their colorful complex. Further development of the method for naked-eye detection of CNˉ in low-concentration aqueous solutions was achieved by using the cellulose papers painted with the dye. The as-prepared testing paper allowed CNˉ sensing in concentrations as low as 2 μM. Evaluation of the dye for antibacterial activities using the well diffusion technique displayed that its inhibitory activity is at least as good as and in some cases superior to ampicillin against the bacterial strains employed in the zone assay. In response to CN¯, the dye changes color from yellow to reddish brown that accounts for its significant interactions with CNˉ and affords a naked-eye sensing method without resorting to any spectroscopic instrumentation. background: Cyanide ion is a serious pollutant of industrial wastewaters and is highly toxic for mammals. objective: A new bioactive azo dye embedding a thiazolidinone heterocyclic core was designed and synthesized for antibacterial application and colorimetric sensing of cyanide ions in organic solutions. method: The structures of prepared dyes were confirmed by 1H NMR, FTIR and UV–vis spectroscopies. It was found to be a fast and sensitive colorogenic sensor for detection of CN¯ ions. result: . In response to CN¯ ion, Spectroscopic studies were investigated of the interaction of synthesized dye with cyanide ion in competition with other anions and different concentrations of cyanide ion. The result of the Job's plot indicating that the stoichiometry binding ratios of synthesized dye and CN¯ is 1:1. Further development of the method for naked-eye detection of cyanide ion in low-concentration aquase solutions was achieved by using the cellulose papers painted with the dye. The as-prepared testing paper allowed CN¯ sensing in concentrations of 2 µM. Evaluation of the dye for antibacterial activities using the well diffusion technique displayed that its inhibitory activity is at least as good as and in some cases superior to ampicillin against the bacterial strains employed in the zone assay.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"2 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139587250","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
aims: To know capability of phytomolecules (alpha-tocopherol, squalene, phytol) in grain Amaranth as drug candidate against AKR1C3 protein, responsible for prostate cancer. background: Amaranth is a pseudocereal, filled with medicinal properties, so for validation in initial stage, docking is cost effective and time saving approach with reliable outcomes. objective: Evaluation of grain Amaranth phytomolecules (alpha-tocopherol, squalene, phytol) as potential compounds against dreadful disease like prostate cancer. method: To evaluation capabilities of alpha-tocopherol, squalene, phytol as drug candidate first they screened for drug-likeliness caharcter along with ADME properties and anti-cancerous characteristics, SWISS-ADME, pkCSM, pass program was utilized for this purpose. second step was, to prepare individual ligand and protein to interaction with the suitable software like BIOVIA. third step was, perform interaction between individual ligand and protein with the assistance of Auto DOCK vina. result: Results were satisfactory, every ligand exhibited significantly and effective bonding with target protein AKR1C3. highest interaction was exhibited by alpha-tocopherol (-9.8 KCal/mol) followed by squalene (-8.9 KCal/mol) subsequently phytol (7.4 KCal/mol). reference drug relugolix showed -7.0 KCal/mol binding energy with target protein AKR1C3. conclusion: docking is an approach to analysis interaction between two molecules. it is cost effective, time saving method to approve a compound as possible drug candidate in initial stage. All three ligands alpha-tocopherol, squalene, phytol showed more and signifacnt interaction with target protein AKR1C3 comparison to reference drug relugolix. so this study can further use in in-vivo study to get more confirmation other: NA
目的：了解谷物苋菜中的植物大分子（α-生育酚、角鲨烯、植醇）作为抗前列腺癌 AKR1C3 蛋白候选药物的能力：苋菜是一种具有药用价值的伪谷物，因此在初始阶段进行验证时，对接是一种成本效益高、节省时间且结果可靠的方法：评估谷物苋菜植物大分子（α-生育酚、角鲨烯、植醇）作为潜在化合物对前列腺癌等可怕疾病的作用：为了评估α-生育酚、角鲨烯和植物醇作为候选药物的能力，首先对它们进行了药物可药性、ADME 特性和抗癌特性的筛选，为此使用了 SWISS-ADME、pkCSM、pass 程序；第二步是使用合适的软件（如 BIOVIA）准备单个配体和蛋白质的相互作用；第三步是在 Auto DOCK vina 的帮助下执行单个配体和蛋白质之间的相互作用：结果令人满意，每种配体都与目标蛋白质 AKR1C3 发生了明显而有效的结合。相互作用最高的是α-生育酚（-9.8 KCal/mol），其次是角鲨烯（-8.9 KCal/mol），然后是植醇（7.4 KCal/mol）。结论：对接是一种分析两个分子间相互作用的方法。它是一种经济、省时的方法，可在初始阶段将化合物批准为可能的候选药物。与参考药物瑞格列奈相比，所有三种配体 alpha-生育酚、角鲨烯和植醇都与目标蛋白 AKR1C3 有更多和更显著的相互作用：不适用
{"title":"Molecular Docking of Phytomolecules of Grain Amaranth (Amaranthus hypochondriacus) with AKR1C3 Protein Involved in Prostate Cancer in Human Beings","authors":"Dinesh Pandey, Manisha Bharti, Anubhav Rana, Sharat Prabhakaran, Rashmi Chauhan","doi":"10.2174/0115701786275607231228094526","DOIUrl":"https://doi.org/10.2174/0115701786275607231228094526","url":null,"abstract":"aims: To know capability of phytomolecules (alpha-tocopherol, squalene, phytol) in grain Amaranth as drug candidate against AKR1C3 protein, responsible for prostate cancer. background: Amaranth is a pseudocereal, filled with medicinal properties, so for validation in initial stage, docking is cost effective and time saving approach with reliable outcomes. objective: Evaluation of grain Amaranth phytomolecules (alpha-tocopherol, squalene, phytol) as potential compounds against dreadful disease like prostate cancer. method: To evaluation capabilities of alpha-tocopherol, squalene, phytol as drug candidate first they screened for drug-likeliness caharcter along with ADME properties and anti-cancerous characteristics, SWISS-ADME, pkCSM, pass program was utilized for this purpose. second step was, to prepare individual ligand and protein to interaction with the suitable software like BIOVIA. third step was, perform interaction between individual ligand and protein with the assistance of Auto DOCK vina. result: Results were satisfactory, every ligand exhibited significantly and effective bonding with target protein AKR1C3. highest interaction was exhibited by alpha-tocopherol (-9.8 KCal/mol) followed by squalene (-8.9 KCal/mol) subsequently phytol (7.4 KCal/mol). reference drug relugolix showed -7.0 KCal/mol binding energy with target protein AKR1C3. conclusion: docking is an approach to analysis interaction between two molecules. it is cost effective, time saving method to approve a compound as possible drug candidate in initial stage. All three ligands alpha-tocopherol, squalene, phytol showed more and signifacnt interaction with target protein AKR1C3 comparison to reference drug relugolix. so this study can further use in in-vivo study to get more confirmation other: NA","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"38 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139580410","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-01-25DOI: 10.2174/0115701786263427231123103651
Mohammad Asif, Mohd Yusuf, Mazen M. Almehmadi, Ahad Alsaiari, Mamdouh Allahyani, Abdulelah Aljuaid, Abdulaziz Alsharif
: Adhatoda vasica (L.) (Acanthaceae) has essential therapeutic roles and is widely used in the indigenous medicine system or Ayurvedic system of medicine. The important goals of the present study are to report the in-silico anti-corona (COVID-19) activity of different phytochemicals present in A. vasica. This study will help to find specific bioactive compounds, and their use as anti- COVID-19 action for human welfare. A. vasica has chemical phytoconstituents with diverse pharmacological activities. These phytoconstituents have been found active against many diseases such as antibacterial, antitubercular, antivirus, antitussive, hepatoprotective, antiinflammatory, antiulcer, antiurolithiatic, abortifacient, radio modulator, cardio-protection, antidiabetic, antioxidant, anticancer, thrombolytic, antimutagenic, etc. Researchers have been lured to the use of natural and sustainable products with substantial therapeutic potential in the current climate of environmental preservation and safe use. These materials permit biological activity, safety, and compatibility with the environment. Using the SARS-CoV-2 spike receptor (6M0J), we evaluated Adhatoda vasica biomolecules for the Covid-19 variant (RBD- COV-2-S). This study is very encouraging and indicates that herbs should be studied more extensively for their therapeutic benefits.
{"title":"Towards Antiviral Potential of Biomolecules Derived from Adhatod avasica as Competent Natural Molecules to Treat COVID-19 Virus Variant","authors":"Mohammad Asif, Mohd Yusuf, Mazen M. Almehmadi, Ahad Alsaiari, Mamdouh Allahyani, Abdulelah Aljuaid, Abdulaziz Alsharif","doi":"10.2174/0115701786263427231123103651","DOIUrl":"https://doi.org/10.2174/0115701786263427231123103651","url":null,"abstract":": Adhatoda vasica (L.) (Acanthaceae) has essential therapeutic roles and is widely used in the indigenous medicine system or Ayurvedic system of medicine. The important goals of the present study are to report the in-silico anti-corona (COVID-19) activity of different phytochemicals present in A. vasica. This study will help to find specific bioactive compounds, and their use as anti- COVID-19 action for human welfare. A. vasica has chemical phytoconstituents with diverse pharmacological activities. These phytoconstituents have been found active against many diseases such as antibacterial, antitubercular, antivirus, antitussive, hepatoprotective, antiinflammatory, antiulcer, antiurolithiatic, abortifacient, radio modulator, cardio-protection, antidiabetic, antioxidant, anticancer, thrombolytic, antimutagenic, etc. Researchers have been lured to the use of natural and sustainable products with substantial therapeutic potential in the current climate of environmental preservation and safe use. These materials permit biological activity, safety, and compatibility with the environment. Using the SARS-CoV-2 spike receptor (6M0J), we evaluated Adhatoda vasica biomolecules for the Covid-19 variant (RBD- COV-2-S). This study is very encouraging and indicates that herbs should be studied more extensively for their therapeutic benefits.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"15 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139587249","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-01-25DOI: 10.2174/0115701786279583231124093402
Vamshikrishna Y. Radhakrishna, Gopal L. Khatik, Bhuvaneshwari S. Vijaya, Vipin A. Nair
: A mild and eco-friendly one-pot, two-step procedure has been developed for the synthesis of 2-hydroxy-N-arylacetamides from 2-chloro-N-arylacetamides. The procedure overcomes the cleavage of the amide linkage in 2-chloroacetamides, which is usually observed under reflux conditions with the hydroxide when the nucleophilic substitution of the halide is attempted. The reactions were performed by refluxing 2-chloro-N-arylacetamides with Cu(OAc)2 and DIPEA in the ethanol medium to facilitate an acetate exchange with the halogen. Subsequently, by the addition of ethanolic KOH solution to the same reaction flask, the ester linkage was selectively cleaved in the presence of the amide, taking advantage of the difference in electrophilicity. The procedure afforded good yields of the desired products, which are valuable intermediates for several biologically active molecules, in a short reaction time with ease of isolation. The experimental conditions employed are simple and offer the possibility of scaling up to higher quantities.
{"title":"A Mild and Eco-friendly, One-pot Synthesis of 2-hydroxy-Narylacetamides from 2-chloro-N-arylacetamides","authors":"Vamshikrishna Y. Radhakrishna, Gopal L. Khatik, Bhuvaneshwari S. Vijaya, Vipin A. Nair","doi":"10.2174/0115701786279583231124093402","DOIUrl":"https://doi.org/10.2174/0115701786279583231124093402","url":null,"abstract":": A mild and eco-friendly one-pot, two-step procedure has been developed for the synthesis of 2-hydroxy-N-arylacetamides from 2-chloro-N-arylacetamides. The procedure overcomes the cleavage of the amide linkage in 2-chloroacetamides, which is usually observed under reflux conditions with the hydroxide when the nucleophilic substitution of the halide is attempted. The reactions were performed by refluxing 2-chloro-N-arylacetamides with Cu(OAc)2 and DIPEA in the ethanol medium to facilitate an acetate exchange with the halogen. Subsequently, by the addition of ethanolic KOH solution to the same reaction flask, the ester linkage was selectively cleaved in the presence of the amide, taking advantage of the difference in electrophilicity. The procedure afforded good yields of the desired products, which are valuable intermediates for several biologically active molecules, in a short reaction time with ease of isolation. The experimental conditions employed are simple and offer the possibility of scaling up to higher quantities.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"222 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139587421","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
: Novel Furan-ring Fused Chalcones (FFC) were synthesized using a radical cyclization reaction of α,β-unsaturated ketones with cyclic ketone as the model reaction to attain this goal. In this study, traditional and microwave-assisted methods for the efficient and cost-effective synthesis of furan-ring fused chalcones in mild reaction conditions are compared and optimized. The goal is to develop a reliable and adaptable synthetic technique that may be used to produce these useful chalcone derivatives quickly and effectively. The optimal experimental conditions for these reactions were carefully determined using two independent methodologies: conventional (Method A) and microwave (Method B). The results indicated that the proposed method B could be used effectively in the future to synthesize novel furans with short reaction times and acceptable yields (87-94 %), and products were purified by column chromatography and preparative thin layer chromatography (PTLC). All new compounds were characterized by 1H-NMR, 13C-NMR, LC-MS, and elemental analyses. result: The aim of this work was to synthesize a new series of furan-ring fused chalcones using two methods and to show the advantages of microwave when it is compared to conventional synthesis methods. As shown in Table 2, a series of novel compounds (3a-3e) were synthesized in one-step reaction between α,β-unsaturated ketones (1a, 1b), and active methylene compounds (2a-d) (Figure 1). The structures of these compounds were confirmed by several spectroscopic methods (1H NMR, 13C NMR, mass spectra, and elemental analysis). conclusion: We have developed a novel, highly efficient, catalyst-free, green protocol for the one-pot three-component synthesis of furan-ring fused chalcones derivatives. This protocol has the advantages of mild reaction conditions, high yields, convenient operation, and environmental friendliness. The technique has various benefits, most notably a decrease in reaction time, good to high yields, and purer results. This work used microwave irradiation, which reduced the reaction time and produced higher yields than the traditional techniques
{"title":"Synthesis, Characterization, and Optimization of Novel Furan-ring Fused Chalcones via Radical Cyclization of α,β-Unsaturated Ketones and Cyclic Ketone","authors":"Emine Vildan Burgaz, Bahareh Noshadi, Mehtap Yakut","doi":"10.2174/0115701786274099231117113559","DOIUrl":"https://doi.org/10.2174/0115701786274099231117113559","url":null,"abstract":": Novel Furan-ring Fused Chalcones (FFC) were synthesized using a radical cyclization reaction of α,β-unsaturated ketones with cyclic ketone as the model reaction to attain this goal. In this study, traditional and microwave-assisted methods for the efficient and cost-effective synthesis of furan-ring fused chalcones in mild reaction conditions are compared and optimized. The goal is to develop a reliable and adaptable synthetic technique that may be used to produce these useful chalcone derivatives quickly and effectively. The optimal experimental conditions for these reactions were carefully determined using two independent methodologies: conventional (Method A) and microwave (Method B). The results indicated that the proposed method B could be used effectively in the future to synthesize novel furans with short reaction times and acceptable yields (87-94 %), and products were purified by column chromatography and preparative thin layer chromatography (PTLC). All new compounds were characterized by 1H-NMR, 13C-NMR, LC-MS, and elemental analyses. result: The aim of this work was to synthesize a new series of furan-ring fused chalcones using two methods and to show the advantages of microwave when it is compared to conventional synthesis methods. As shown in Table 2, a series of novel compounds (3a-3e) were synthesized in one-step reaction between α,β-unsaturated ketones (1a, 1b), and active methylene compounds (2a-d) (Figure 1). The structures of these compounds were confirmed by several spectroscopic methods (1H NMR, 13C NMR, mass spectra, and elemental analysis). conclusion: We have developed a novel, highly efficient, catalyst-free, green protocol for the one-pot three-component synthesis of furan-ring fused chalcones derivatives. This protocol has the advantages of mild reaction conditions, high yields, convenient operation, and environmental friendliness. The technique has various benefits, most notably a decrease in reaction time, good to high yields, and purer results. This work used microwave irradiation, which reduced the reaction time and produced higher yields than the traditional techniques","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"34 4 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139556255","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-01-24DOI: 10.2174/0115701786273621231121064121
Omid Marvi, Sattar Arshadi, Bita Baghernejad
aims: This work presents a clean and convenient synthesis of various β-enaminones incuding 5,5-dimethyl-3-aminocyclohex-2-enones in good to excellent yields from the reaction of different primary amines with 1,3-dicarbonyl compounds by employing T3P® as a catalyst and performing the reaction under microwave irradiation and solvent-free conditions. background: This work presents a clean and convenient synthesis of various β-enaminones incuding 5,5-dimethyl-3-aminocyclohex-2-enones in good to excellent yields from the reaction of different primary amines with 1,3-dicarbonyl compounds by employing T3P® as a catalyst and performing the reaction under microwave irradiation and solvent-free conditions. This one-pot rapid reaction proceeded readily and tolerated a variety of functional groups. objective: A mixture of 2,5-pentandione, primary amine and T3P® (50% in AcOEt) was irradiated for appropriate time under microwave at 80 °C. method: A mixture of 2,5-pentandione, primary amine and T3P® (50% in AcOEt) was irradiated for appropriate time under microwave at 80 °C. After completing the reaction (TLC) and cooling to r.t., ethyl acetate and saturated aqueous NaHCO3 solution was added. The aqueous phase was extracted ethyl acetate. The combined organic layer washed with brine, dried over Na2SO4, filtered and solvent is removed under reduced pressure to afford the product, which recrystallized from diisopropyl ether. result: The presented results exhibit a better catalytic activity of T3P in the synthesis of enaminones. It can be concluded that T3P is the best catalyst as it took only a few minutes for completion of reaction with excellent yield of product that indicates T3P is more effective and more efficient compared to other catalysts. A comparison of efficiency of the present procedure with some of heterogeneous solid catalysts was evaluated as well. Clearly higher yield was established in this procedure compared to other catalysts. Furthermore, reaction of amines with dimedone were investigated as well, delivering excellent yields conclusion: The reaction catalyzed by T3P under microwave irradiation supplies a comprehensive method for the synthesis of enaminones. This work will find widespread application in the synthesis of these compounds. T3P is efficient and non-toxic, which makes the process economic, convenient, and benign. other: This work will find widespread application in the synthesis of these compounds. T3P is efficient and non-toxic, which makes the process economic, convenient, and benign.
{"title":"An Efficient Propylphosphonic Anhydride (T3P®)-Mediated MW-induced Solvent-free Rapid Synthesis of Enamino Esters and Ketones including 5,5- Dimethyl-3-aminocyclohex-2-enones","authors":"Omid Marvi, Sattar Arshadi, Bita Baghernejad","doi":"10.2174/0115701786273621231121064121","DOIUrl":"https://doi.org/10.2174/0115701786273621231121064121","url":null,"abstract":"aims: This work presents a clean and convenient synthesis of various β-enaminones incuding 5,5-dimethyl-3-aminocyclohex-2-enones in good to excellent yields from the reaction of different primary amines with 1,3-dicarbonyl compounds by employing T3P® as a catalyst and performing the reaction under microwave irradiation and solvent-free conditions. background: This work presents a clean and convenient synthesis of various β-enaminones incuding 5,5-dimethyl-3-aminocyclohex-2-enones in good to excellent yields from the reaction of different primary amines with 1,3-dicarbonyl compounds by employing T3P® as a catalyst and performing the reaction under microwave irradiation and solvent-free conditions. This one-pot rapid reaction proceeded readily and tolerated a variety of functional groups. objective: A mixture of 2,5-pentandione, primary amine and T3P® (50% in AcOEt) was irradiated for appropriate time under microwave at 80 °C. method: A mixture of 2,5-pentandione, primary amine and T3P® (50% in AcOEt) was irradiated for appropriate time under microwave at 80 °C. After completing the reaction (TLC) and cooling to r.t., ethyl acetate and saturated aqueous NaHCO3 solution was added. The aqueous phase was extracted ethyl acetate. The combined organic layer washed with brine, dried over Na2SO4, filtered and solvent is removed under reduced pressure to afford the product, which recrystallized from diisopropyl ether. result: The presented results exhibit a better catalytic activity of T3P in the synthesis of enaminones. It can be concluded that T3P is the best catalyst as it took only a few minutes for completion of reaction with excellent yield of product that indicates T3P is more effective and more efficient compared to other catalysts. A comparison of efficiency of the present procedure with some of heterogeneous solid catalysts was evaluated as well. Clearly higher yield was established in this procedure compared to other catalysts. Furthermore, reaction of amines with dimedone were investigated as well, delivering excellent yields conclusion: The reaction catalyzed by T3P under microwave irradiation supplies a comprehensive method for the synthesis of enaminones. This work will find widespread application in the synthesis of these compounds. T3P is efficient and non-toxic, which makes the process economic, convenient, and benign. other: This work will find widespread application in the synthesis of these compounds. T3P is efficient and non-toxic, which makes the process economic, convenient, and benign.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139556212","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-01-24DOI: 10.2174/0115701786269449231116062157
Shaoguang Sun, Yucheng Jiang, Hui Mao, Shuya Cui
: 1,7-dimethylxanthine is a critical intermediate in the pharmaceutical industry. In this paper, a scalable route for the synthesis of 1,7-dimethylxanthine was developed. The method in-cluded two steps: (1) acylation reaction of ethyl 4-amino-1-methyl-1H-imidazole-5- carboxylate was carried out by using commercially available methylcarbamoyl chloride as the starting materi-al; (2) through cyclization of pyrimidine ring with aqueous sodium hydroxide, 1,7-dimethylxanthine was obtained with a total yield of 80%, and its HPLC purity was 99% by area. The method is very efficient and readily adaptable to kilogram scale, and because of the cycliza-tion reaction process in aqueous conditions, this route is worthy of exploration for industrial ap-plication. result: 1, 7-dimethylxanthine was prepared with an overall yield of 80% with an HPLC purity of 99% by area. conclusion: We developed a new synthetic route for making 1, 7-dimethyl xanthine with high yield. The method uses commercially available raw materials to synthesize 1, 7-dimethyl xanthine on kilogram scale. Because of higher yield, higher purity and completion of cyclization reaction in aqueous condition, it was robustness, lower cost, and small environment impact. This route is worthy of exploration for industrial application.
{"title":"Scalable, Chromatography-Free Synthesis of 1,7-dimethylxanthine","authors":"Shaoguang Sun, Yucheng Jiang, Hui Mao, Shuya Cui","doi":"10.2174/0115701786269449231116062157","DOIUrl":"https://doi.org/10.2174/0115701786269449231116062157","url":null,"abstract":": 1,7-dimethylxanthine is a critical intermediate in the pharmaceutical industry. In this paper, a scalable route for the synthesis of 1,7-dimethylxanthine was developed. The method in-cluded two steps: (1) acylation reaction of ethyl 4-amino-1-methyl-1H-imidazole-5- carboxylate was carried out by using commercially available methylcarbamoyl chloride as the starting materi-al; (2) through cyclization of pyrimidine ring with aqueous sodium hydroxide, 1,7-dimethylxanthine was obtained with a total yield of 80%, and its HPLC purity was 99% by area. The method is very efficient and readily adaptable to kilogram scale, and because of the cycliza-tion reaction process in aqueous conditions, this route is worthy of exploration for industrial ap-plication. result: 1, 7-dimethylxanthine was prepared with an overall yield of 80% with an HPLC purity of 99% by area. conclusion: We developed a new synthetic route for making 1, 7-dimethyl xanthine with high yield. The method uses commercially available raw materials to synthesize 1, 7-dimethyl xanthine on kilogram scale. Because of higher yield, higher purity and completion of cyclization reaction in aqueous condition, it was robustness, lower cost, and small environment impact. This route is worthy of exploration for industrial application.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"40 1 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139556198","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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