Pub Date : 2024-01-24DOI: 10.2174/0115701786275818231117053307
Adeleh Moshtaghi Zonouz, Davoud Moghani
: Indole–acrylonitrile hybrids were synthesized via a catalyst-free reaction of aromatic aldehydes and 3-(cyanoacetyl)indole in aqueous media. Also, indole-coumarin hybrids were synthesized via a domino reaction of salicylaldehyde derivatives and 3-(cyanoacetyl)indole in the presence of ammonium acetate in aqueous media. The advantages of the present protocol are high yields, short reaction times, mild reaction conditions, operational simplicity, and environmentally benign, and also there is no need to purification of products. objective: The development of hybrid molecules through the combination of indole and other heterocycles may lead to compounds with interesting biological activity. method: The Knoevenagel condensation reaction of 3-(cyanoacetyl)indole with benzaldehyde derivatives was carried out in EtOH/H2O 1:1 in reflux condition and 3-aryl-2-(1H-indol-3-ylcarbonyl)acrylonitrile 3a-h were obtained in excellent yields. The indole-coumarin hybrids 5a-g were obtained from the reaction of salicylaldehyde derivatives and 3-(cyanoacetyl)indole in EtOH/H2O (2:1) in the presence of 1 equivalent ammonium acetate as a catalyst at reflux condition.
{"title":"A Green and Convenient Approach for the Synthesis of Indole–acrylonitrile and Indole-coumarin Hybrids in Aqueous Media","authors":"Adeleh Moshtaghi Zonouz, Davoud Moghani","doi":"10.2174/0115701786275818231117053307","DOIUrl":"https://doi.org/10.2174/0115701786275818231117053307","url":null,"abstract":": Indole–acrylonitrile hybrids were synthesized via a catalyst-free reaction of aromatic aldehydes and 3-(cyanoacetyl)indole in aqueous media. Also, indole-coumarin hybrids were synthesized via a domino reaction of salicylaldehyde derivatives and 3-(cyanoacetyl)indole in the presence of ammonium acetate in aqueous media. The advantages of the present protocol are high yields, short reaction times, mild reaction conditions, operational simplicity, and environmentally benign, and also there is no need to purification of products. objective: The development of hybrid molecules through the combination of indole and other heterocycles may lead to compounds with interesting biological activity. method: The Knoevenagel condensation reaction of 3-(cyanoacetyl)indole with benzaldehyde derivatives was carried out in EtOH/H2O 1:1 in reflux condition and 3-aryl-2-(1H-indol-3-ylcarbonyl)acrylonitrile 3a-h were obtained in excellent yields. The indole-coumarin hybrids 5a-g were obtained from the reaction of salicylaldehyde derivatives and 3-(cyanoacetyl)indole in EtOH/H2O (2:1) in the presence of 1 equivalent ammonium acetate as a catalyst at reflux condition.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"10 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139556128","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}
:: Chemicals and poisons in the body interfere with the cell cycle and inhibit the growth of cancer cells. In this way, the function of chemicals in the body is controlled by taking anti-cancer drugs. Due to the degradability and compatibility of carbon nanotubes and boron nitride with the environment, they can act as suitable drug carriers for the transfer of anticancer drugs and deliver the drugs to the target cells. In the current work, the encapsulation of Formestane (FMS) anticancer drug into the carbon (CNT) and boron nitride (BNNT) (8,8) nanotubes was investigated for the first time using the density functional theory: B3LYP/3-21G* and the natural bond orbital analysis in the gas phase. Using natural bond orbital analysis, the charge transfer between FMS drug and CNT and BNNT nanotubes (8,8)/ FMS (BNNT/FMS) complexes were explored. Based on the results obtained from the calculation of encapsulation energy, it was found that the adsorption process was favorable. The interaction effects of FMS drug and CNT and BNNT (8,8) nanotubes on the natural bond orbital charge, the chemical shift parameters, and electronic properties were also evaluated. This study revealed that CNT and BNNT (8,8) nanotubes can be a suitable carrier for FMS drug delivery. The ultraviolet-visible spectra of the FMS drug, the CNT and BNNT (8,8), and the BNNT/FMS complexes were computed using time-dependent density functional theory (DFT: B3LYP) calculations. method: Using natural bond orbital analysis, the charge transfer between FMS drug and CNT and BNNT nanotubes (8,8)/ FMS (BNNT/FMS) complexes were explored. result: Based on the results obtained from the calculation of encapsulation energy, it was found that the adsorption process was favorable. The interaction effects of FMS drug and CNT and BNNT (8,8) nanotubes on the natural bond orbital charge, the chemical shift parameters, and electronic properties were also evaluated. conclusion: This study revealed that CNT and BNNT (8,8) nanotubes can be a suitable carrier for FMS drug delivery. The ultra violet-visible spectra of FMS drug and the CNT and BNNT (8,8), BNNT/FMS complexes were computed using time-dependent density functional theory (DFT: B3LYP) calculations. other: In this work, the capability of BNNTs and CNTs as delivery vehicles of FMS was explored by ab initio based DFT calculations. The electronic properties and interaction mechanisms of FMS with BNNTs and CNTs have been explored in detail. The intermolecular interactions between FMS and nanotubes were investigated by analyzing the optimized structure and interaction energies. Calculated adsorption energies show that FMS is adsorbed more stably on CNTs than BNNTs, which indicates that CNTs may be more potential delivery vehicles of FMS. The DOS plots, HOMO-LUMO NBO, and spectroscopic (excited states, UV) properties were performed to study the influence of drug adsorption on nanotubes. Therefore, FMS encapsulation was in good agreement with DFT calculations.
{"title":"DFT Study of Nanotubes as the Drug Delivery Vehicles for an Anticancer Drug","authors":"Nasrin Masnabadi, Shiva Masoudi, Maryam Hosseinzadeh","doi":"10.2174/0115701786265839240103115143","DOIUrl":"https://doi.org/10.2174/0115701786265839240103115143","url":null,"abstract":":: Chemicals and poisons in the body interfere with the cell cycle and inhibit the growth of cancer cells. In this way, the function of chemicals in the body is controlled by taking anti-cancer drugs. Due to the degradability and compatibility of carbon nanotubes and boron nitride with the environment, they can act as suitable drug carriers for the transfer of anticancer drugs and deliver the drugs to the target cells. In the current work, the encapsulation of Formestane (FMS) anticancer drug into the carbon (CNT) and boron nitride (BNNT) (8,8) nanotubes was investigated for the first time using the density functional theory: B3LYP/3-21G* and the natural bond orbital analysis in the gas phase. Using natural bond orbital analysis, the charge transfer between FMS drug and CNT and BNNT nanotubes (8,8)/ FMS (BNNT/FMS) complexes were explored. Based on the results obtained from the calculation of encapsulation energy, it was found that the adsorption process was favorable. The interaction effects of FMS drug and CNT and BNNT (8,8) nanotubes on the natural bond orbital charge, the chemical shift parameters, and electronic properties were also evaluated. This study revealed that CNT and BNNT (8,8) nanotubes can be a suitable carrier for FMS drug delivery. The ultraviolet-visible spectra of the FMS drug, the CNT and BNNT (8,8), and the BNNT/FMS complexes were computed using time-dependent density functional theory (DFT: B3LYP) calculations. method: Using natural bond orbital analysis, the charge transfer between FMS drug and CNT and BNNT nanotubes (8,8)/ FMS (BNNT/FMS) complexes were explored. result: Based on the results obtained from the calculation of encapsulation energy, it was found that the adsorption process was favorable. The interaction effects of FMS drug and CNT and BNNT (8,8) nanotubes on the natural bond orbital charge, the chemical shift parameters, and electronic properties were also evaluated. conclusion: This study revealed that CNT and BNNT (8,8) nanotubes can be a suitable carrier for FMS drug delivery. The ultra violet-visible spectra of FMS drug and the CNT and BNNT (8,8), BNNT/FMS complexes were computed using time-dependent density functional theory (DFT: B3LYP) calculations. other: In this work, the capability of BNNTs and CNTs as delivery vehicles of FMS was explored by ab initio based DFT calculations. The electronic properties and interaction mechanisms of FMS with BNNTs and CNTs have been explored in detail. The intermolecular interactions between FMS and nanotubes were investigated by analyzing the optimized structure and interaction energies. Calculated adsorption energies show that FMS is adsorbed more stably on CNTs than BNNTs, which indicates that CNTs may be more potential delivery vehicles of FMS. The DOS plots, HOMO-LUMO NBO, and spectroscopic (excited states, UV) properties were performed to study the influence of drug adsorption on nanotubes. Therefore, FMS encapsulation was in good agreement with DFT calculations.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"13 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139556202","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 : 2024-01-22DOI: 10.2174/0115701786273862231116105938
Aman Bhalla, Garima Modi, Pankaj Kumar, Jaswinder Kaur, Shiwani Berry, S. S. Bari, Bimal K. Banik
: The enantioselective synthesis of chiral cis-3-hydroxyazetidin-2-ones mediated by Porcine Pancreatic Lipase (PPL) via hydrolysis of cis-3-(chloro acetoxy) azetidin-2-ones in the presence of a phosphate buffer (0.1M, pH = 7.2) in acetonitrile at a temperature range of 25-35 °C was optimized. Under the optimized reaction conditions, the influence of various electron withdrawing/donating/neutral groups on ester functionality of cis-3-(substituted acetoxy)azetidin-2- ones towards hydrolysis was extensively studied, and the bromoacetoxy, propanyloxy, and formyloxy groups provided moderate to good yields of 90%, 91%, and 81%, respectively. Moreover, the chiral cis-3-hydroxyazetidin-2-ones underwent acetylation, and their enantiomeric excess was assessed using the 1H NMR technique, employing chiral shift reagents. To gain insights into the active sites of the biocatalyst, molecular docking studies of compounds 5(a-i) with pancreatic lipase (PDB ID: 1LBS) were carried out. Additionally, the proposed interaction of substituents with the biocatalyst established the absolute stereochemistry of the target chiral cis-3-hydroxyazetidin-2-ones using Seebach's model in comparison to Jone's models. objective: With an aim to explore the general applicability and to ascertain whether 3-substituted acetoxyazetidin-2-ones would give a similar series of optically active compounds, we envisaged the comprehensive studies on the enantioselective synthesis of chiral cis-3-hydroxyazetidin-2-ones from synthesized cis-3-substitutedacetoxyazetidin-2-ones. We here describe extended PPL hydrolysis studies, wherein, the influence of replacement of the hydrogen of the acetate functionality with halide (-Cl, -Br), alkyl (-CH3), aryl (-C6H5) and aralkyl (-CH2C6H5) groups is discussed. Also, the effects of substitution of methyl group of acetate with hydrogen (-H) and aryl (-C6H5) groups upon PPL hydrolysis is investigated. Further the binding mode of cis-3-(substituted acetoxy)azetidin-2-ones with pancreatic lipase (PDB ID: 1LBS) and assessment of the impact of structural modifications has been carried out using molecular docking studies.
{"title":"Optimization and Effect of Substituents on the Transformation of 3-(Substituted acetoxy)azetidin-2-ones to Chiral 3-Hydroxyazetidin-2-ones, Molecular Docking and Enantiomeric Excess Determination","authors":"Aman Bhalla, Garima Modi, Pankaj Kumar, Jaswinder Kaur, Shiwani Berry, S. S. Bari, Bimal K. Banik","doi":"10.2174/0115701786273862231116105938","DOIUrl":"https://doi.org/10.2174/0115701786273862231116105938","url":null,"abstract":": The enantioselective synthesis of chiral cis-3-hydroxyazetidin-2-ones mediated by Porcine Pancreatic Lipase (PPL) via hydrolysis of cis-3-(chloro acetoxy) azetidin-2-ones in the presence of a phosphate buffer (0.1M, pH = 7.2) in acetonitrile at a temperature range of 25-35 °C was optimized. Under the optimized reaction conditions, the influence of various electron withdrawing/donating/neutral groups on ester functionality of cis-3-(substituted acetoxy)azetidin-2- ones towards hydrolysis was extensively studied, and the bromoacetoxy, propanyloxy, and formyloxy groups provided moderate to good yields of 90%, 91%, and 81%, respectively. Moreover, the chiral cis-3-hydroxyazetidin-2-ones underwent acetylation, and their enantiomeric excess was assessed using the 1H NMR technique, employing chiral shift reagents. To gain insights into the active sites of the biocatalyst, molecular docking studies of compounds 5(a-i) with pancreatic lipase (PDB ID: 1LBS) were carried out. Additionally, the proposed interaction of substituents with the biocatalyst established the absolute stereochemistry of the target chiral cis-3-hydroxyazetidin-2-ones using Seebach's model in comparison to Jone's models. objective: With an aim to explore the general applicability and to ascertain whether 3-substituted acetoxyazetidin-2-ones would give a similar series of optically active compounds, we envisaged the comprehensive studies on the enantioselective synthesis of chiral cis-3-hydroxyazetidin-2-ones from synthesized cis-3-substitutedacetoxyazetidin-2-ones. We here describe extended PPL hydrolysis studies, wherein, the influence of replacement of the hydrogen of the acetate functionality with halide (-Cl, -Br), alkyl (-CH3), aryl (-C6H5) and aralkyl (-CH2C6H5) groups is discussed. Also, the effects of substitution of methyl group of acetate with hydrogen (-H) and aryl (-C6H5) groups upon PPL hydrolysis is investigated. Further the binding mode of cis-3-(substituted acetoxy)azetidin-2-ones with pancreatic lipase (PDB ID: 1LBS) and assessment of the impact of structural modifications has been carried out using molecular docking studies.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"115 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139556222","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 : 2024-01-22DOI: 10.2174/0115701786284466240105074539
Antonio M. Ruda, Jonathan D. Moseley
: A series of novel activated esters of morphine were synthesized as alternatives to the triflate ester and submitted to hydrogenolysis conditions. Of these, only the novel nonaflate ester could be transformed with full conversion into the useful intermediate, 3-deoxymorphine, which was isolated in good yield and high purity without chromatography. This conversion proceeded significantly faster than for the triflate ester and with synthesis of the intermediate nonaflate at much reduced cost, an important factor for the large-scale preparation of 3-deoxymorphine in drug development projects.
{"title":"Synthesis and Development of a Nonaflate Ester in the Large-Scale Preparation of 3-Deoxymorphine","authors":"Antonio M. Ruda, Jonathan D. Moseley","doi":"10.2174/0115701786284466240105074539","DOIUrl":"https://doi.org/10.2174/0115701786284466240105074539","url":null,"abstract":": A series of novel activated esters of morphine were synthesized as alternatives to the triflate ester and submitted to hydrogenolysis conditions. Of these, only the novel nonaflate ester could be transformed with full conversion into the useful intermediate, 3-deoxymorphine, which was isolated in good yield and high purity without chromatography. This conversion proceeded significantly faster than for the triflate ester and with synthesis of the intermediate nonaflate at much reduced cost, an important factor for the large-scale preparation of 3-deoxymorphine in drug development projects.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"117 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139556252","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 : 2024-01-21DOI: 10.2174/0115701786269569231221041108
Masoumeh Shahi, Donya Falahati, Fatemeh Ashtari
: The development of density functional theory has led to the consideration of computational chemistry in the design and development of interactions of new drugs in the gas phase with nanocarriers. In the present study, the interaction of ibuprofen with alginic acid (as a nanocarrier) has been investigated using density functional theory (DFT) in the gas phase (M06-2X/6-31+G*). A study on the effects of ibuprofen’s interaction with the compounds present in alginic acid has been conducted, focusing on the electronic properties, the chemical shift tensors, and the natural bond orbital. Based on the results of UV spectra, the compound 6-thioguanine has been found to be changed into an alginic acid/ibuprofen complex. The quantum theory of atoms in molecules showed the interaction of ibuprofen to be mainly driven by non-covalent bonds with alginic acid during complex formation. A hydrogen bond has been found to be formed between the oxygen atoms of alginic acid and ibuprofen's hydrogen atoms. Consequently, alginic acid has been used for delivering ibuprofen to diseased cells.
{"title":"Density Functional Theory Study of Interaction between Ibuprofen and Alginic Acid for Targeted Drug Delivery","authors":"Masoumeh Shahi, Donya Falahati, Fatemeh Ashtari","doi":"10.2174/0115701786269569231221041108","DOIUrl":"https://doi.org/10.2174/0115701786269569231221041108","url":null,"abstract":": The development of density functional theory has led to the consideration of computational chemistry in the design and development of interactions of new drugs in the gas phase with nanocarriers. In the present study, the interaction of ibuprofen with alginic acid (as a nanocarrier) has been investigated using density functional theory (DFT) in the gas phase (M06-2X/6-31+G*). A study on the effects of ibuprofen’s interaction with the compounds present in alginic acid has been conducted, focusing on the electronic properties, the chemical shift tensors, and the natural bond orbital. Based on the results of UV spectra, the compound 6-thioguanine has been found to be changed into an alginic acid/ibuprofen complex. The quantum theory of atoms in molecules showed the interaction of ibuprofen to be mainly driven by non-covalent bonds with alginic acid during complex formation. A hydrogen bond has been found to be formed between the oxygen atoms of alginic acid and ibuprofen's hydrogen atoms. Consequently, alginic acid has been used for delivering ibuprofen to diseased cells.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"24 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139518585","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 : 2024-01-12DOI: 10.2174/0115701786271328231207092337
Marwa Derbel, Iteb Trabelsi, Kamel Essid
: Lipid esters are prepared from mixed fatty anhydrides by esterification. These esters are high-value-added intermediates used in industrial applications. We describe the synthesis and characterization of esters using salicylic acid and mixed anhydrides with zinc oxide as catalysts. To achieve maximum reaction efficiency, we varied the mixed anhydride and studied some parameters in the reaction, such as the molar ratio (anhydride/alcohol) and the amount of catalyst. The esterification reaction was realized with some primary and secondary alcohols in the presence of resin Amberlyst15. The best yield of the palmitic ester was obtained in the case of mixed 4-chlorobenzoic palmitic anhydride. We obtained 53% of fatty ester. Moreover, we also studied the reactivity of certain mixed anhydrides for the esterification reaction of salicylic acid in the presence of a Lewis acid as a heterogeneous catalyst. The anhydrides were prepared in the presence of triethylamine in the organic solvent by a reaction between fatty acid and acid chloride. Mixed aromatic palmitic were more reactive and selective than the aliphatic anhydrides. The palmitic group was the most involved in acylation. Good yields of fatty esters were obtained with total conversion of mixed anhydrides.
{"title":"Study on the Reactivity of Mixed Carboxylic Palmitic Anhydrides via the Esterification Reaction Using Heterogeneous Catalyst","authors":"Marwa Derbel, Iteb Trabelsi, Kamel Essid","doi":"10.2174/0115701786271328231207092337","DOIUrl":"https://doi.org/10.2174/0115701786271328231207092337","url":null,"abstract":": Lipid esters are prepared from mixed fatty anhydrides by esterification. These esters are high-value-added intermediates used in industrial applications. We describe the synthesis and characterization of esters using salicylic acid and mixed anhydrides with zinc oxide as catalysts. To achieve maximum reaction efficiency, we varied the mixed anhydride and studied some parameters in the reaction, such as the molar ratio (anhydride/alcohol) and the amount of catalyst. The esterification reaction was realized with some primary and secondary alcohols in the presence of resin Amberlyst15. The best yield of the palmitic ester was obtained in the case of mixed 4-chlorobenzoic palmitic anhydride. We obtained 53% of fatty ester. Moreover, we also studied the reactivity of certain mixed anhydrides for the esterification reaction of salicylic acid in the presence of a Lewis acid as a heterogeneous catalyst. The anhydrides were prepared in the presence of triethylamine in the organic solvent by a reaction between fatty acid and acid chloride. Mixed aromatic palmitic were more reactive and selective than the aliphatic anhydrides. The palmitic group was the most involved in acylation. Good yields of fatty esters were obtained with total conversion of mixed anhydrides.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"95 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139461614","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 : 2024-01-12DOI: 10.2174/0115701786280075231211094705
Sanjib Kumar Karmee
: Biodiesel and oleo-chemical industries have been producing huge quantities of glycerol as a by-product. Value-added products can be synthesized from glycerol through different chemical and enzymatic reactions, such as oxidation, carbonylation, reforming, acetalyzation, etherification, dehydration, hydrogenolysis, hydrolysis, esterification, and transesterification. Glycerol is a low-cost polyol that can be converted into glycerol carbonate, which has potential applications in polymer and biobased non-isocyanate polyurethanes industries (Bio-NIPUs). The present contribution is the first of its kind to report on the synthesis of glycerol carbonate via catalyst and solvent-free transesterification of glycerol with dimethyl carbonate under conventional as well as microwave heating. Additionally, a comparative study of conventional and microwave-assisted transesterification was performed. Under conventional heating, 78% glycerol carbonate is obtained at 120 o C in 36 hours, whereas, using microwaves, 92% of glycerol carbonate can be achieved in 30 minutes. Presently, biomass-based heterogeneous materials are used in catalysis due to their importance within the context of sustainability. In line with this, in this work, a series of green catalysts, namely, molecular sieves (MS, 4Å), HβZeolite, Montmorillonite K-10 clay, activated carbon prepared from the shell of groundnut (Arachis hypogaea), and biochar from sawdust pyrolysis were successfully employed. Glycerol carbonate was thoroughly characterized by 1 H and 13C NMR, FT-IR and MS. The method described here is facile and green since the utilization of bioresource (glycerol) for the production of glycerol carbonate is performed under microwave.
:生物柴油和油脂化学工业产生了大量的副产品甘油。甘油可通过不同的化学和酶反应合成增值产品，如氧化、羰基化、重整、乙酰化、醚化、脱水、氢解、水解、酯化和酯交换。甘油是一种可转化为碳酸甘油酯的低成本多元醇，在聚合物和生物基非异氰酸酯聚氨酯行业（Bio-NIPUs）中具有潜在的应用价值。本论文首次报道了在常规和微波加热条件下，通过催化剂和无溶剂的碳酸二甲酯化反应合成碳酸甘油酯。此外，还对常规和微波辅助酯交换反应进行了比较研究。在常规加热条件下，在 120 o C 温度下，36 小时内可获得 78% 的碳酸甘油酯，而使用微波，30 分钟内可获得 92% 的碳酸甘油酯。目前，基于生物质的异质材料因其在可持续发展方面的重要性而被用于催化。有鉴于此，本研究成功采用了一系列绿色催化剂，即分子筛（MS，4 Å）、Hβ沸石、蒙脱石 K-10 粘土、从落花生（Arachis hypogaea）外壳制备的活性炭，以及从锯末热解制得的生物炭。通过 1 H 和 13C NMR、FT-IR 和 MS 对碳酸甘油酯进行了全面的表征。由于利用生物资源（甘油）生产碳酸甘油酯的方法是在微波条件下进行的，因此该方法既简便又绿色。
{"title":"Can Glycerol Carbonate be Synthesized Without a Catalyst?","authors":"Sanjib Kumar Karmee","doi":"10.2174/0115701786280075231211094705","DOIUrl":"https://doi.org/10.2174/0115701786280075231211094705","url":null,"abstract":": Biodiesel and oleo-chemical industries have been producing huge quantities of glycerol as a by-product. Value-added products can be synthesized from glycerol through different chemical and enzymatic reactions, such as oxidation, carbonylation, reforming, acetalyzation, etherification, dehydration, hydrogenolysis, hydrolysis, esterification, and transesterification. Glycerol is a low-cost polyol that can be converted into glycerol carbonate, which has potential applications in polymer and biobased non-isocyanate polyurethanes industries (Bio-NIPUs). The present contribution is the first of its kind to report on the synthesis of glycerol carbonate via catalyst and solvent-free transesterification of glycerol with dimethyl carbonate under conventional as well as microwave heating. Additionally, a comparative study of conventional and microwave-assisted transesterification was performed. Under conventional heating, 78% glycerol carbonate is obtained at 120 o C in 36 hours, whereas, using microwaves, 92% of glycerol carbonate can be achieved in 30 minutes. Presently, biomass-based heterogeneous materials are used in catalysis due to their importance within the context of sustainability. In line with this, in this work, a series of green catalysts, namely, molecular sieves (MS, 4Å), HβZeolite, Montmorillonite K-10 clay, activated carbon prepared from the shell of groundnut (Arachis hypogaea), and biochar from sawdust pyrolysis were successfully employed. Glycerol carbonate was thoroughly characterized by 1 H and 13C NMR, FT-IR and MS. The method described here is facile and green since the utilization of bioresource (glycerol) for the production of glycerol carbonate is performed under microwave.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"41 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-01-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139461641","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 : 2023-12-27DOI: 10.2174/0115701786274678231124101033
Ravi K. Mittal, Raghav Mishra, Vikram Sharma, Isha Mishra
:: 1,3,4-Thiadiazole has garnered considerable attention in the scientific community due to its captivating molecular structure and ability to serve as a foundation for creating novel pharmaceutical compounds. Numerous medications feature the 1,3,4-thiadiazole ring in their chemical structure, highlighting its relevance and efficacy in pharmaceutical research and development. The key objective of this comprehensive review is to provide an understandable overview of the chemistry and diverse pharmacological activities associated with 1,3,4-thiadiazole compounds. The manuscript was compiled by conducting a thorough literature review, which included an in-depth analysis of globally esteemed scientific research databases. The remarkable chemical characteristics and diverse pharmacological impacts of 1,3,4-Thiadiazole highlight its significant potential as a structural scaffold for the development of novel therapeutic substances. Based on the information available on synthetic molecules that incorporate the 1,3,4-thiadiazole framework and their wide range of uses, it is reasonable to expect significant advancements in the near future and the possibility of employing these compounds in different domains.
{"title":"1,3,4-Thiadiazole: A Versatile Scaffold for Drug Discovery","authors":"Ravi K. Mittal, Raghav Mishra, Vikram Sharma, Isha Mishra","doi":"10.2174/0115701786274678231124101033","DOIUrl":"https://doi.org/10.2174/0115701786274678231124101033","url":null,"abstract":":: 1,3,4-Thiadiazole has garnered considerable attention in the scientific community due to its captivating molecular structure and ability to serve as a foundation for creating novel pharmaceutical compounds. Numerous medications feature the 1,3,4-thiadiazole ring in their chemical structure, highlighting its relevance and efficacy in pharmaceutical research and development. The key objective of this comprehensive review is to provide an understandable overview of the chemistry and diverse pharmacological activities associated with 1,3,4-thiadiazole compounds. The manuscript was compiled by conducting a thorough literature review, which included an in-depth analysis of globally esteemed scientific research databases. The remarkable chemical characteristics and diverse pharmacological impacts of 1,3,4-Thiadiazole highlight its significant potential as a structural scaffold for the development of novel therapeutic substances. Based on the information available on synthetic molecules that incorporate the 1,3,4-thiadiazole framework and their wide range of uses, it is reasonable to expect significant advancements in the near future and the possibility of employing these compounds in different domains.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"22 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2023-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139055868","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 : 2023-12-27DOI: 10.2174/0115701786273932230927062616
Shilpi Pathak, Neetu Agrawal, Sonam Gaur
: Pyrazine belongs to the 1, 4-diazines family, which is a significant class of heterocyclic compounds. Various pyrazine derivatives have been produced and successfully confirmed as medicines with various pharmacological activities like anti-inflammatory, antitubercular, anticancer, antibacterial, and neurological activity, with some of them becoming clinically utilized pharmaceuticals globally. This review includes a survey on pyrazine derivatives possessing different pharmacological activities. The class of pyrazine-based potential medications has grown rapidly in terms of both the absolute quantity of studied compounds and the range of various biological activities. Additionally, there is a lot of potential for this scaffold, which medicinal chemists ought to investigate for the creation of novel potential drug candidates.
{"title":"A Review on Diverse Biological Activity of Heterocyclic Nucleus Pyrazine and its Derivatives: A Key for the Researchers","authors":"Shilpi Pathak, Neetu Agrawal, Sonam Gaur","doi":"10.2174/0115701786273932230927062616","DOIUrl":"https://doi.org/10.2174/0115701786273932230927062616","url":null,"abstract":": Pyrazine belongs to the 1, 4-diazines family, which is a significant class of heterocyclic compounds. Various pyrazine derivatives have been produced and successfully confirmed as medicines with various pharmacological activities like anti-inflammatory, antitubercular, anticancer, antibacterial, and neurological activity, with some of them becoming clinically utilized pharmaceuticals globally. This review includes a survey on pyrazine derivatives possessing different pharmacological activities. The class of pyrazine-based potential medications has grown rapidly in terms of both the absolute quantity of studied compounds and the range of various biological activities. Additionally, there is a lot of potential for this scaffold, which medicinal chemists ought to investigate for the creation of novel potential drug candidates.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"17 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2023-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139051362","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 : 2023-11-28DOI: 10.2174/0115701786226175231023112257
Awadhesh Kumar, Akash Ved, Karuna S. shukla, Amit Kumar Nigam
: The Ayurvedic formulations' evaluation is very wide and deep. The project's goal was to evaluate the phytochemistry and antioxidant activity of Ayurvedic formulations used to treat digestive disorders. Herbal formulations are typically available as single or mixed formulations of multiple plant constituents, and it is critical to quantify the number of markers present in such formulations to ensure the product's high quality. The extract of formulations (Ajmodadi churna, Avipattikar churna, and Sanjivani vati) was subjected to physicochemical screening, phytochemical screening, HPTLC, and antioxidant activity was observed in the current study. Three ayurvedic formulations (Sanjivini vati, Ajmodadi Churna, and Avipattikar Churna) were studied physicochemically in this study. The extraction process determined the total phenolic and flavonoid content. The antioxidant capacity of the selected formulation was calculated by three methods; total antioxidant capacity, ferric-reducing power, and DPPH scavenging activity. The active constituent was isolated using the HPTLC method. This study shows that the formulations Ajmodai churna, Avipattikar churna, and Sanjivani vati are important sources of antioxidant compounds. The active constituent was isolated using the HPTLC method. The HPTLC technique showed the presence of phenolics and terpenoids that are responsible for antioxidant activity. Phenolics and Terpenoids, due to their antioxidant activity, are used as an important source for digestive disorders.
{"title":"Phytochemical Evaluation of Selected Ayurvedic Formulations and Evaluate their Antioxidant Activity","authors":"Awadhesh Kumar, Akash Ved, Karuna S. shukla, Amit Kumar Nigam","doi":"10.2174/0115701786226175231023112257","DOIUrl":"https://doi.org/10.2174/0115701786226175231023112257","url":null,"abstract":": The Ayurvedic formulations' evaluation is very wide and deep. The project's goal was to evaluate the phytochemistry and antioxidant activity of Ayurvedic formulations used to treat digestive disorders. Herbal formulations are typically available as single or mixed formulations of multiple plant constituents, and it is critical to quantify the number of markers present in such formulations to ensure the product's high quality. The extract of formulations (Ajmodadi churna, Avipattikar churna, and Sanjivani vati) was subjected to physicochemical screening, phytochemical screening, HPTLC, and antioxidant activity was observed in the current study. Three ayurvedic formulations (Sanjivini vati, Ajmodadi Churna, and Avipattikar Churna) were studied physicochemically in this study. The extraction process determined the total phenolic and flavonoid content. The antioxidant capacity of the selected formulation was calculated by three methods; total antioxidant capacity, ferric-reducing power, and DPPH scavenging activity. The active constituent was isolated using the HPTLC method. This study shows that the formulations Ajmodai churna, Avipattikar churna, and Sanjivani vati are important sources of antioxidant compounds. The active constituent was isolated using the HPTLC method. The HPTLC technique showed the presence of phenolics and terpenoids that are responsible for antioxidant activity. Phenolics and Terpenoids, due to their antioxidant activity, are used as an important source for digestive disorders.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"51 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2023-11-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138516057","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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