Pub Date : 2024-01-26DOI: 10.2174/0115701786272432231211100408
Sailu Betala, Naveen Puram, Udayasri Bhanothu
: Our primary research objective is to create and formulate small ring heterocycles with enhanced biological efficacy. Amide functionalized trifluoromethyl thieno[2,3-b]pyridine derivatives as a series were prepared starting from reaction between 1,3 di-ketone and thiocyanoacetamide and obtained pyridine 3. Compound 3 reacts with bromoethyl acetate and obtained compound 4, further compound 4 on reaction with diverse substituted aromatic and aliphatic amines to get amide derivatives 5a-d, 6a-d and 7a-h. All the final compounds evaluated for anti cancer activity against four human cancer cell lines such as ‘HeLa - Cervical cancer (CCL-2); COLO 205- Colon cancer (CCL- 222); HepG2 - Liver cancer (HB-8065); MCF7 - Breast cancer (HTB-22)’ and promising compounds 7d, 7e and 7f have been identified. For compounds 7d, 7e and 7f molecular docking interactions have been identified. background: heterocyclic chemistry method: Synthesis result: we synthesized amide functionalized thienopyridone derivates and evaluated for anticancer activity four human cancer cell lines
{"title":"Novel Amide Functionalized Trifluoromethyl thieno[2,3-b]pyridine Derivatives: Anti-cancer Activity and Molecular Docking Studies","authors":"Sailu Betala, Naveen Puram, Udayasri Bhanothu","doi":"10.2174/0115701786272432231211100408","DOIUrl":"https://doi.org/10.2174/0115701786272432231211100408","url":null,"abstract":": Our primary research objective is to create and formulate small ring heterocycles with enhanced biological efficacy. Amide functionalized trifluoromethyl thieno[2,3-b]pyridine derivatives as a series were prepared starting from reaction between 1,3 di-ketone and thiocyanoacetamide and obtained pyridine 3. Compound 3 reacts with bromoethyl acetate and obtained compound 4, further compound 4 on reaction with diverse substituted aromatic and aliphatic amines to get amide derivatives 5a-d, 6a-d and 7a-h. All the final compounds evaluated for anti cancer activity against four human cancer cell lines such as ‘HeLa - Cervical cancer (CCL-2); COLO 205- Colon cancer (CCL- 222); HepG2 - Liver cancer (HB-8065); MCF7 - Breast cancer (HTB-22)’ and promising compounds 7d, 7e and 7f have been identified. For compounds 7d, 7e and 7f molecular docking interactions have been identified. background: heterocyclic chemistry method: Synthesis result: we synthesized amide functionalized thienopyridone derivates and evaluated for anticancer activity four human cancer cell lines","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"323 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139579571","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 : 2024-01-26DOI: 10.2174/0115701786270260231215101046
Yildiz Uygun Cebeci, Sengul Alpay Karaoglu
: In this study, synthesis of 1,2,4 triazo1e-fluoroquino1one hybrid compounds was rea1ized. 7a-d hybrid compound was obtained as a result of mannich reaction with 6a-b triazole compounds norfloxacin and ciprofloxacin. 1H-NMR, 13C-NMR, Mass Spectrometry and Elemental Analysis confirmed the structures of a11 synthesized compounds. The antimicrobia1 activities of a11 compounds were investigated, and it was observed that 7a-d compounds, which are mannich bases, showed excellent activity.
{"title":"1,2,4-Triazole-conjugated Fluoroquinolones as Potential Candidates for New Antibacterial Agents","authors":"Yildiz Uygun Cebeci, Sengul Alpay Karaoglu","doi":"10.2174/0115701786270260231215101046","DOIUrl":"https://doi.org/10.2174/0115701786270260231215101046","url":null,"abstract":": In this study, synthesis of 1,2,4 triazo1e-fluoroquino1one hybrid compounds was rea1ized. 7a-d hybrid compound was obtained as a result of mannich reaction with 6a-b triazole compounds norfloxacin and ciprofloxacin. 1H-NMR, 13C-NMR, Mass Spectrometry and Elemental Analysis confirmed the structures of a11 synthesized compounds. The antimicrobia1 activities of a11 compounds were investigated, and it was observed that 7a-d compounds, which are mannich bases, showed excellent activity.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"66 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139579690","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}
: Quinoline is one of the promising and prominent biologically active N-based heterocyclic compounds. This review paper aims to discuss the synthetic approaches, summarized from various research articles on the preparation of quinoline derivatives intended for different therapeutic activities like antifungal activity, anticancer activity, anticonvulsant activity, antitubercular activity, antimalarial activity, anti-Alzheimer activity and so on. The comprehensive study complies with all related publications and trademark publications demonstrating the synthesis and biological aspects of quinoline derivatives. Various types of quinoline hybrids were synthesized and treated for therapeutic activity, including anticancer, antitubercular, anti-Alzheimer, antioxidant, and antifungal activity, which have been analyzed. Quinoline is a planner hetero-aromatic compound with the chemical formula C9H7N. Several wellknown synthetic routes to the quinoline skeleton include Friedlander synthesis, Knorr quinoline synthesis, and Skraup reaction. Researchers may use other techniques or alter current strategies to reach their objectives, depending on what exact structure and therapeutic action they are investigating. The availability of starting materials, reaction conditions, scalability, desired regioselectivity, and functionalization of the quinoline core all have a role in the choice of synthetic method. This review covers the latest literature and knowledge on the synthetic procedures for numerous quinoline and its derivatives and their biological and pharmacological application.
:喹啉是一种具有广阔前景和突出生物活性的 N 基杂环化合物。本综述论文旨在讨论喹啉衍生物的合成方法，这些方法是从各种研究文章中总结出来的，用于制备具有不同治疗活性的喹啉衍生物，如抗真菌活性、抗癌活性、抗惊厥活性、抗结核活性、抗疟活性、抗老年痴呆活性等。这项综合研究符合所有证明喹啉衍生物的合成和生物学方面的相关出版物和商标出版物。研究人员合成了各种类型的喹啉杂化物，并对其治疗活性进行了分析，包括抗癌、抗结核、抗老年痴呆、抗氧化和抗真菌活性。喹啉是一种平面杂芳香族化合物，化学式为 C9H7N。几种著名的喹啉骨架合成路线包括弗里德兰德合成法、克诺尔喹啉合成法和斯克劳普反应。研究人员可根据所研究的确切结构和治疗作用，使用其他技术或改变现有策略来达到目的。起始材料的可用性、反应条件、可扩展性、所需的区域选择性以及喹啉核心的官能化等因素都会影响合成方法的选择。本综述涵盖了有关多种喹啉及其衍生物的合成程序及其生物学和药理学应用的最新文献和知识。
{"title":"Insight into the Various Approaches Undertaken for the Synthesis of Quinoline Hybrids Imparting Diverse Therapeutic Activities","authors":"Ruchi Sharma, Chandana Majee, Rupa Mazumder, Avijit Mazumder, Swarupanjali Padhi, Akshay Kumar","doi":"10.2174/0115701786279549231228125141","DOIUrl":"https://doi.org/10.2174/0115701786279549231228125141","url":null,"abstract":": Quinoline is one of the promising and prominent biologically active N-based heterocyclic compounds. This review paper aims to discuss the synthetic approaches, summarized from various research articles on the preparation of quinoline derivatives intended for different therapeutic activities like antifungal activity, anticancer activity, anticonvulsant activity, antitubercular activity, antimalarial activity, anti-Alzheimer activity and so on. The comprehensive study complies with all related publications and trademark publications demonstrating the synthesis and biological aspects of quinoline derivatives. Various types of quinoline hybrids were synthesized and treated for therapeutic activity, including anticancer, antitubercular, anti-Alzheimer, antioxidant, and antifungal activity, which have been analyzed. Quinoline is a planner hetero-aromatic compound with the chemical formula C9H7N. Several wellknown synthetic routes to the quinoline skeleton include Friedlander synthesis, Knorr quinoline synthesis, and Skraup reaction. Researchers may use other techniques or alter current strategies to reach their objectives, depending on what exact structure and therapeutic action they are investigating. The availability of starting materials, reaction conditions, scalability, desired regioselectivity, and functionalization of the quinoline core all have a role in the choice of synthetic method. This review covers the latest literature and knowledge on the synthetic procedures for numerous quinoline and its derivatives and their biological and pharmacological application.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"39 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139579687","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 : 2024-01-26DOI: 10.2174/0115701786282079231229050431
Jingwen Ji, Zafar Iqbal, Liuyan Li, Jian Sun, Pengjuan Zhou, Lijuan Zhai, Lili He, Dong Tang, Jinbo Ji, Haikang Yang, Zhixiang Yang
: N1-caffeoyl-N10-dihydrocaffeoylspermidine (Scotanamine D), a spermidine alkaloid isolated from various plants, is a medicinally valuable natural product. Recent studies have pointed out several health benefits of this compound. However, its synthetic procedures are still not described in the literature. We report the synthesis of this compound following two different schemes comprising multiple steps with excellent overall yields, which are 57% and 81%, respectively. These two synthetic schemes, which use commercially available and cheaper starting materials, can facilitate the large-scale manufacturing of Scotanamine D.
{"title":"Synthesis of N1-caffeoyl-N10-dihydrocaffeoylspermidine (Scotanamine D)","authors":"Jingwen Ji, Zafar Iqbal, Liuyan Li, Jian Sun, Pengjuan Zhou, Lijuan Zhai, Lili He, Dong Tang, Jinbo Ji, Haikang Yang, Zhixiang Yang","doi":"10.2174/0115701786282079231229050431","DOIUrl":"https://doi.org/10.2174/0115701786282079231229050431","url":null,"abstract":": N1-caffeoyl-N10-dihydrocaffeoylspermidine (Scotanamine D), a spermidine alkaloid isolated from various plants, is a medicinally valuable natural product. Recent studies have pointed out several health benefits of this compound. However, its synthetic procedures are still not described in the literature. We report the synthesis of this compound following two different schemes comprising multiple steps with excellent overall yields, which are 57% and 81%, respectively. These two synthetic schemes, which use commercially available and cheaper starting materials, can facilitate the large-scale manufacturing of Scotanamine D.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"4 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139579689","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 : 2024-01-26DOI: 10.2174/0115701786283334231228104931
Roshanak Hariri, Aida Iraji, Somayeh Mojtabavi, Mina Saeedi, Mohammad Ali Faramarzi, Mohsen Amini, Tahmineh Akbarzadeh
: Carbohydrates are an important group of biomolecules that have received special attention due to their significant role in the design and synthesis of new bioactive compounds. In this study, a new class of 5-arylisoxazole-glucose hybrids was designed and synthesized for evaluation of their inhibitory effects on α-glucosidase, α-amylase, and tyrosinase. The target compounds depicted selective α-glucosidase inhibitory activity over α-amylase, which is an important factor in reducing probable gastrointestinal problems in the treatment of type 2 diabetes. In this respect, compound 9a, possessing the phenylisoxazole group, was found to be the most potent α-glucosidase inhibitor (IC50 = 292.2 ± 0.1 µM) compared to acarbose (IC50 = 750.2 ± 0.1 µM) as the positive control. All compounds were also evaluated for their anti-tyrosinase effect, and among them, compound 9j, containing a fluoroaryl moiety, showed potent activity (IC50 = 50.1 ± 6.3 µM) in comparison to kojic acid (IC50 = 23.6 ± 2.6 µM). Also, docking studies were performed to investigate the probable mode of action, which indicated the construction of important H-bonding interactions between the sugar moiety and the enzyme’s active sites. According to the results, hybrids containing heterocycles attached to glucose can be used to inhibit α-glucosidase.
{"title":"Synthesis of New Glucose-containing 5-Arylisoxazoles and their Enzyme Inhibitory Activity","authors":"Roshanak Hariri, Aida Iraji, Somayeh Mojtabavi, Mina Saeedi, Mohammad Ali Faramarzi, Mohsen Amini, Tahmineh Akbarzadeh","doi":"10.2174/0115701786283334231228104931","DOIUrl":"https://doi.org/10.2174/0115701786283334231228104931","url":null,"abstract":": Carbohydrates are an important group of biomolecules that have received special attention due to their significant role in the design and synthesis of new bioactive compounds. In this study, a new class of 5-arylisoxazole-glucose hybrids was designed and synthesized for evaluation of their inhibitory effects on α-glucosidase, α-amylase, and tyrosinase. The target compounds depicted selective α-glucosidase inhibitory activity over α-amylase, which is an important factor in reducing probable gastrointestinal problems in the treatment of type 2 diabetes. In this respect, compound 9a, possessing the phenylisoxazole group, was found to be the most potent α-glucosidase inhibitor (IC50 = 292.2 ± 0.1 µM) compared to acarbose (IC50 = 750.2 ± 0.1 µM) as the positive control. All compounds were also evaluated for their anti-tyrosinase effect, and among them, compound 9j, containing a fluoroaryl moiety, showed potent activity (IC50 = 50.1 ± 6.3 µM) in comparison to kojic acid (IC50 = 23.6 ± 2.6 µM). Also, docking studies were performed to investigate the probable mode of action, which indicated the construction of important H-bonding interactions between the sugar moiety and the enzyme’s active sites. According to the results, hybrids containing heterocycles attached to glucose can be used to inhibit α-glucosidase.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"30 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139579701","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 : 2024-01-26DOI: 10.2174/0115701786263337231227113513
Fayezeh Yousefnejad, Mohammad Hossein Sayahi, Ali Mazzam, Fatemeh Gholami, Nader Tanideh, Cambyz Irajie, Helia Tayebi, Fatemeh Rasekh, Bagher Larijani, Maliheh Barazandeh Tehrani, Mohammad Mahdavi, Aida Iraji
: Tyrosinase is a critical enzyme responsible for pigmentation disorders, and tyrosinase inhibition is an established strategy to treat hyperpigmentation. In the current study, cinnamic acidbased derivatives were designed and synthesized. All synthesized compounds were confirmed using IR, 1 HNMR, 13CNMR, and CNH analysis. The inhibitory potencies of all derivatives against tyrosinase were determined, and it was shown that 5m bearing para-chloro moiety exhibits an IC50 value of 77.62 µmol/L. Analysis of enzyme kinetic studies revealed that 5m is an uncompetitive inhibitor. In silico studies against tyrosinase predicted possible binding mode in the pocket such that 5m formed critical interactions with both Cu co-factors within the binding site. This study presents the potential of aryl-substituted cinnamic acids that can benefit various cosmetic formulations as depigmentation agents.
{"title":"Structure-based Drug Design of New Cinnamic Acid Derivatives as Tyrosinase Inhibitors","authors":"Fayezeh Yousefnejad, Mohammad Hossein Sayahi, Ali Mazzam, Fatemeh Gholami, Nader Tanideh, Cambyz Irajie, Helia Tayebi, Fatemeh Rasekh, Bagher Larijani, Maliheh Barazandeh Tehrani, Mohammad Mahdavi, Aida Iraji","doi":"10.2174/0115701786263337231227113513","DOIUrl":"https://doi.org/10.2174/0115701786263337231227113513","url":null,"abstract":": Tyrosinase is a critical enzyme responsible for pigmentation disorders, and tyrosinase inhibition is an established strategy to treat hyperpigmentation. In the current study, cinnamic acidbased derivatives were designed and synthesized. All synthesized compounds were confirmed using IR, 1 HNMR, 13CNMR, and CNH analysis. The inhibitory potencies of all derivatives against tyrosinase were determined, and it was shown that 5m bearing para-chloro moiety exhibits an IC50 value of 77.62 µmol/L. Analysis of enzyme kinetic studies revealed that 5m is an uncompetitive inhibitor. In silico studies against tyrosinase predicted possible binding mode in the pocket such that 5m formed critical interactions with both Cu co-factors within the binding site. This study presents the potential of aryl-substituted cinnamic acids that can benefit various cosmetic formulations as depigmentation agents.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"38 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139580287","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 : 2024-01-26DOI: 10.2174/0115701786278928231218113855
Ashok Pise, Shripad M Patil, Ajit P Ingale
: A protocol for the Chemoselective N-Boc protection of various types of amines has been developed. This includes heteroaryl, aliphatic, and alicyclic amines. The process makes use of malic acid as a catalyst and operates efficiently at ambient temperature without the need for solvents. This technique has been proven to effectively protect a wide range of functionalized amines containing both electron-donating and electron-withdrawing substituents. The benefits of this method include its fast reaction rate, high selectivity, excellent yield, catalyst recyclability, and environmentally friendly conditions. background: A green, efficient, and solvent-free reaction enlarge for Chemoselective N-Boc protection of aromatic, aliphatic, and heterocyclic amine using malic acid-catalyzed under ambient temperature. The described technique successfully performs the N-Boc on a wide range of functionalized aliphatic, aromatic, and hetero-aromatic amines. The advantage of this method has studied the different types of amines that contain electron-donating as well as electron-withdrawing substituents. The reaction works by rapid reaction rate, high selectivity, solvent-free, excellent yield, catalyst recycle, and greener route. This work presents a green, economical, and eco-friendly protocol. result: In the present work to investigate the scope and disadvantages of this solvent-free N-ter-butoxycarbonylation of amine derivatives catalyzed under malic acid, we can study with the model the reaction of aniline react with di-ter-butyl carbonate (1:1 mmol) and malic acid (15 mol%) under solvent-free reaction conditions to give ter-butyl-phenyl carbonate. (Scheme 2) The reaction was completed within 5 min at room temperature and the corresponding N-Boc protected aniline was obtained in 98 % yield. To appreciate the role of malic acid on the N-Boc protection of amine, we have analyzed the reaction of aniline with di-ter-butyl carbonate in catalyst-free conditions at room temperature. It should be noted that the catalyst-free condition and reaction time of 12 h, were obtained in a 25 % yield. Whereas after 24 hours, it was observed to increase only 37 % yield. All amines derivatives undergo reaction at room temperature without a catalyst for 24 h. The N-Boc protection of amine under the malic acid applies to increases yield and reaction time as compared to the absence of a catalyst.
{"title":"Malic Acid as a Green Catalyst for the N-Boc Protection under Solvent-free Condition","authors":"Ashok Pise, Shripad M Patil, Ajit P Ingale","doi":"10.2174/0115701786278928231218113855","DOIUrl":"https://doi.org/10.2174/0115701786278928231218113855","url":null,"abstract":": A protocol for the Chemoselective N-Boc protection of various types of amines has been developed. This includes heteroaryl, aliphatic, and alicyclic amines. The process makes use of malic acid as a catalyst and operates efficiently at ambient temperature without the need for solvents. This technique has been proven to effectively protect a wide range of functionalized amines containing both electron-donating and electron-withdrawing substituents. The benefits of this method include its fast reaction rate, high selectivity, excellent yield, catalyst recyclability, and environmentally friendly conditions. background: A green, efficient, and solvent-free reaction enlarge for Chemoselective N-Boc protection of aromatic, aliphatic, and heterocyclic amine using malic acid-catalyzed under ambient temperature. The described technique successfully performs the N-Boc on a wide range of functionalized aliphatic, aromatic, and hetero-aromatic amines. The advantage of this method has studied the different types of amines that contain electron-donating as well as electron-withdrawing substituents. The reaction works by rapid reaction rate, high selectivity, solvent-free, excellent yield, catalyst recycle, and greener route. This work presents a green, economical, and eco-friendly protocol. result: In the present work to investigate the scope and disadvantages of this solvent-free N-ter-butoxycarbonylation of amine derivatives catalyzed under malic acid, we can study with the model the reaction of aniline react with di-ter-butyl carbonate (1:1 mmol) and malic acid (15 mol%) under solvent-free reaction conditions to give ter-butyl-phenyl carbonate. (Scheme 2) The reaction was completed within 5 min at room temperature and the corresponding N-Boc protected aniline was obtained in 98 % yield. To appreciate the role of malic acid on the N-Boc protection of amine, we have analyzed the reaction of aniline with di-ter-butyl carbonate in catalyst-free conditions at room temperature. It should be noted that the catalyst-free condition and reaction time of 12 h, were obtained in a 25 % yield. Whereas after 24 hours, it was observed to increase only 37 % yield. All amines derivatives undergo reaction at room temperature without a catalyst for 24 h. The N-Boc protection of amine under the malic acid applies to increases yield and reaction time as compared to the absence of a catalyst.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"28 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139580774","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 : 2024-01-26DOI: 10.2174/0115701786277621231226160450
Dhananjay N. Gaikwad, Suresh T. Gaikwad, Rajesh K. Manjul, Anjali S. Rajbhoj, Dayanand M. Suryavanshi
: The Fe (III)-Cu (II) binary oxide magnetic nanocatalyst emerges as an environmentally friendly and highly efficient solid acid catalyst, demonstrating remarkable utility in the one-pot synthesis of 2, 4, 5-trisubstituted imidazole and 1,4-dihydropyridine compounds, all achieved under solvent-free conditions. A facile co-precipitation method was used to synthesize nanostructured Fe-Cu binary oxide. Notably, this Fe-Cu binary oxide magnetic nanocatalyst proves its eco-friendly credentials as an exceptionally efficient and reusable catalyst, offering ease of handling, recovery, and multiple uses with minimal reactivity loss. Furthermore, the Fe (III)-Cu (II) binary oxide magnetic nanocatalyst's magnetic separability enhances its practicality, allowing for effortless catalyst retrieval after reactions. Significantly, the structural characteristics are meticulously elucidated through advanced analytical techniques, including 1 H and 13C nuclear magnetic resonance (NMR) spectroscopy. This work presents a versatile and sustainable solution for catalysis, with wide-reaching implications for green chemistry and the development of reusable, efficient catalysts for organic synthesis. The exceptional performance and eco-friendliness of the Fe-Cu binary oxide magnetic nanocatalyst underscore its practical significance. Fe-Cu binary oxide magnetic nanocatalyst exhibits the highest catalytic activity compared to others. The employment of this catalyst consistently delivers excellent yields in the target reactions, highlighting its potential to contribute positively to sustainable chemical processes.
{"title":"Nanostructured Iron (III)-Copper (II) Binary Oxide as a Highly Efficient Magnetically Recoverable Nanocatalyst for Facile One-pot Synthesis of 2, 4, 5-trisubstituted Imidazole and 1, 4-dihydro Pyridine Derivatives under Solvent-free Conditions","authors":"Dhananjay N. Gaikwad, Suresh T. Gaikwad, Rajesh K. Manjul, Anjali S. Rajbhoj, Dayanand M. Suryavanshi","doi":"10.2174/0115701786277621231226160450","DOIUrl":"https://doi.org/10.2174/0115701786277621231226160450","url":null,"abstract":": The Fe (III)-Cu (II) binary oxide magnetic nanocatalyst emerges as an environmentally friendly and highly efficient solid acid catalyst, demonstrating remarkable utility in the one-pot synthesis of 2, 4, 5-trisubstituted imidazole and 1,4-dihydropyridine compounds, all achieved under solvent-free conditions. A facile co-precipitation method was used to synthesize nanostructured Fe-Cu binary oxide. Notably, this Fe-Cu binary oxide magnetic nanocatalyst proves its eco-friendly credentials as an exceptionally efficient and reusable catalyst, offering ease of handling, recovery, and multiple uses with minimal reactivity loss. Furthermore, the Fe (III)-Cu (II) binary oxide magnetic nanocatalyst's magnetic separability enhances its practicality, allowing for effortless catalyst retrieval after reactions. Significantly, the structural characteristics are meticulously elucidated through advanced analytical techniques, including 1 H and 13C nuclear magnetic resonance (NMR) spectroscopy. This work presents a versatile and sustainable solution for catalysis, with wide-reaching implications for green chemistry and the development of reusable, efficient catalysts for organic synthesis. The exceptional performance and eco-friendliness of the Fe-Cu binary oxide magnetic nanocatalyst underscore its practical significance. Fe-Cu binary oxide magnetic nanocatalyst exhibits the highest catalytic activity compared to others. The employment of this catalyst consistently delivers excellent yields in the target reactions, highlighting its potential to contribute positively to sustainable chemical processes.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"7 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139580632","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 : 2024-01-26DOI: 10.2174/0115701786261811231126174656
Yan-fen Shi, Zheng Wu, Jie Mou, Hong-hua Yuan
: The utilization of palladium catalysts in cross-coupling reactions has emerged as a highly promising method for the facile formation of aryl C-N bonds, operating under mild conditions. In this study, we present an efficient approach for the synthesis of methyl N-phenyl carbamate derivatives through the intermolecular amidation of aryl chlorides, catalyzed by Xphos Pd G2. The developed protocol has demonstrated remarkable efficacy, offering several advantages. Notably, the intermolecular amidation reaction exhibited good chemoselectivity, allowing for the precise targeting of desired C-N bond formations while maintaining the integrity of other functional groups. Additionally, this methodology showcases exceptional functional group compatibility, accommodating a diverse array of moieties, including sensitive groups that are traditionally challenging to handle. The Xphos Pd G2 catalyst has proven to be instrumental in orchestrating this transformation, exhibiting high catalytic activity and selectivity. Furthermore, this protocol stands out for its operational simplicity, making it a practical choice for synthetic chemists seeking a straightforward and reliable route to access methyl N-phenyl carbamate derivatives. Overall, this study not only expands the synthetic toolbox for C-N bond formations, but also underscores the significance of palladium-catalyzed methodologies in modern organic synthesis. The reported findings hold substantial promise for applications in medicinal chemistry and material science, where the facile construction of aryl C-N bonds is of paramount importance
{"title":"Synthesis of Methyl N-phenylcarbamate Derivatives by Xphos Pd G2 Catalyzed Intermolecular Amidation Reaction","authors":"Yan-fen Shi, Zheng Wu, Jie Mou, Hong-hua Yuan","doi":"10.2174/0115701786261811231126174656","DOIUrl":"https://doi.org/10.2174/0115701786261811231126174656","url":null,"abstract":": The utilization of palladium catalysts in cross-coupling reactions has emerged as a highly promising method for the facile formation of aryl C-N bonds, operating under mild conditions. In this study, we present an efficient approach for the synthesis of methyl N-phenyl carbamate derivatives through the intermolecular amidation of aryl chlorides, catalyzed by Xphos Pd G2. The developed protocol has demonstrated remarkable efficacy, offering several advantages. Notably, the intermolecular amidation reaction exhibited good chemoselectivity, allowing for the precise targeting of desired C-N bond formations while maintaining the integrity of other functional groups. Additionally, this methodology showcases exceptional functional group compatibility, accommodating a diverse array of moieties, including sensitive groups that are traditionally challenging to handle. The Xphos Pd G2 catalyst has proven to be instrumental in orchestrating this transformation, exhibiting high catalytic activity and selectivity. Furthermore, this protocol stands out for its operational simplicity, making it a practical choice for synthetic chemists seeking a straightforward and reliable route to access methyl N-phenyl carbamate derivatives. Overall, this study not only expands the synthetic toolbox for C-N bond formations, but also underscores the significance of palladium-catalyzed methodologies in modern organic synthesis. The reported findings hold substantial promise for applications in medicinal chemistry and material science, where the facile construction of aryl C-N bonds is of paramount importance","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"7 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139579700","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}
: In this study, high yields of various cyclic carbonates were obtained by employing the drug celecoxib to promote the coupling reaction of CO2 and epoxide using tetrabutylammonium bromide. This strategy enabled the synthesis of benzoic acid, phenylpropiolic acid, and 2, 4- quinazolinedione. In addition, the model reaction mechanism was proposed. background: Cyclic carbonates have a high economic value and broad application as intermediate in fine chemicals, monomers for synthesizing active polymers, polar aprotic solvents in organic reactions and electrolytes in lithium-ion batteries.
{"title":"Celecoxib Catalyzed the Coupling Reaction of Epoxide and CO2","authors":"Ling Wu, Xiaocheng Xia, Wenying An, Wenshan Cui, Yue Liu, Wei Lv, Fengtian Wu","doi":"10.2174/0115701786276731231206113215","DOIUrl":"https://doi.org/10.2174/0115701786276731231206113215","url":null,"abstract":": In this study, high yields of various cyclic carbonates were obtained by employing the drug celecoxib to promote the coupling reaction of CO2 and epoxide using tetrabutylammonium bromide. This strategy enabled the synthesis of benzoic acid, phenylpropiolic acid, and 2, 4- quinazolinedione. In addition, the model reaction mechanism was proposed. background: Cyclic carbonates have a high economic value and broad application as intermediate in fine chemicals, monomers for synthesizing active polymers, polar aprotic solvents in organic reactions and electrolytes in lithium-ion batteries.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"26 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139579708","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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