Pub Date : 2024-09-18DOI: 10.2174/0113852728301305240828073241
Amrita Yadav, Pooja A. Chawla, Simranpreet K. Wahan, Viney Chawla
A series of 4-thiazolidinone was synthesized and characterized by means of TLC, melting point, and spectral data like IR, 1H NMR, and Mass spectra. The anti-inflammatory activity of the synthesized compounds was determined via in vivo studies. The antioxidant properties of the synthesized compounds were determined by carrageenan-induced rat paw edema model. The synthesized compounds (A1-A14) showed significant anti-inflammatory and antioxidant activities. The most promising results for both antioxidant and antiinflammatory activity were exhibited by compound A8 which may emerge as a potent anti-inflammatory agent with potential free radical scavenging activity. Molecular docking studies were carried out to determine the interaction of compounds into the active site of COX-2 inhibitor (PDB ID: 3LN1), which suggested compound A8 to have the best docking score by showing interactions with ASP483 and LYS478.
{"title":"Exploring the Potential of Novel 4-Thiazolidinone Derivatives as Dual Anti-inflammatory and Antioxidant Agents: Synthesis, Pharmacological Activity and Docking Analysis","authors":"Amrita Yadav, Pooja A. Chawla, Simranpreet K. Wahan, Viney Chawla","doi":"10.2174/0113852728301305240828073241","DOIUrl":"https://doi.org/10.2174/0113852728301305240828073241","url":null,"abstract":"A series of 4-thiazolidinone was synthesized and characterized by means of TLC, melting point, and spectral data like IR, 1H NMR, and Mass spectra. The anti-inflammatory activity of the synthesized compounds was determined via in vivo studies. The antioxidant properties of the synthesized compounds were determined by carrageenan-induced rat paw edema model. The synthesized compounds (A1-A14) showed significant anti-inflammatory and antioxidant activities. The most promising results for both antioxidant and antiinflammatory activity were exhibited by compound A8 which may emerge as a potent anti-inflammatory agent with potential free radical scavenging activity. Molecular docking studies were carried out to determine the interaction of compounds into the active site of COX-2 inhibitor (PDB ID: 3LN1), which suggested compound A8 to have the best docking score by showing interactions with ASP483 and LYS478.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"26 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142265002","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-18DOI: 10.2174/0113852728301326240827115106
Nandita Nawal, Pooja A. Chawla, Sharma Arvind Virendra, Viney Chawla
aims: A series of sixteen new 4-(substituted phenyl) - 6-(substituted phenylamino)-3, 4-dihydropyrimidine-2(1H)-ones/thiones derivatives have been synthesized in two step reaction. background: Free radicals are widely known to play a significant part in the inflammatory process. Many non-steroidal anti-inflammatory medicines have been shown to work as radical scavengers or as inhibitors of free radical generation. Inflammation is a part of the vascular tissues' complicated biological reaction to adverse stimuli like bacteria, damaged cells, or irritants. The organism's protective response to damaging stimuli is inflammation, which aims to get rid of them and start the healing process. The inflammatory response has several advantageous effects, such as stopping the spread of dangerous substances to nearby tissues, getting rid of cell waste and infections, and getting the body ready for repair objective: To synthesize new derivatives as anti-inflammatory and antioxidant agents. method: In first step chalcones (I1-I6) was obtained and in the second step, these chalcones were reacted with urea and thiourea in the presence of potassium hydroxide to obtain the corresponding pyrimidinones and thiopyrimidinones. The structures of the synthesized compounds 4-(substituted phenyl)-6-(substituted phenylamino)-3,4-dihydropyrimidine-2(1H)-ones/thione derivatives are investigated by means of TLC (visualized it in Iodine chamber), IR, mass, 1H-NMR spectral and elemental analysis. The title compounds evaluated for anti-inflammatory as well as antioxidant activity. Anti-inflammatory activity in vivo was carried out by carrageenan induced rat-paw edema method and compared with standard drug diclofenac sodium and antioxidant activity was measured by DPPH, FRAP and Hydrogen peroxide (H2O2) method and compared with standard ascorbic acid. result: Electron donating groups showed better antioxidant activity as compared to electron withdrawing ones in both activities. All the compounds exhibited good to moderate activity. Compound DHPM8 shows better antioxidant activity and compound DHPM6 shows better anti-inflammatory activity while compound DHPM11 shows minimum antioxidant as well as anti-inflammatory activity than other compounds. conclusion: To better understanding, we have performed molecular docking simulation. The molecular docking studies revealed that all synthesized compound were showed good receptor binding interaction in which compound 9 had highest docking score of 9.8 due to interaction with CYS36, PRO153, TYR130, GLY45, LEU152, ARG469, LYS468 and GLU465. other: NA
{"title":"3,4-Dihydropyrimidine-2(1H)-one/thione Derivatives as Anti-inflammatory and Antioxidant Agents: Synthesis, Biological Activity, and Docking Studies","authors":"Nandita Nawal, Pooja A. Chawla, Sharma Arvind Virendra, Viney Chawla","doi":"10.2174/0113852728301326240827115106","DOIUrl":"https://doi.org/10.2174/0113852728301326240827115106","url":null,"abstract":"aims: A series of sixteen new 4-(substituted phenyl) - 6-(substituted phenylamino)-3, 4-dihydropyrimidine-2(1H)-ones/thiones derivatives have been synthesized in two step reaction. background: Free radicals are widely known to play a significant part in the inflammatory process. Many non-steroidal anti-inflammatory medicines have been shown to work as radical scavengers or as inhibitors of free radical generation. Inflammation is a part of the vascular tissues' complicated biological reaction to adverse stimuli like bacteria, damaged cells, or irritants. The organism's protective response to damaging stimuli is inflammation, which aims to get rid of them and start the healing process. The inflammatory response has several advantageous effects, such as stopping the spread of dangerous substances to nearby tissues, getting rid of cell waste and infections, and getting the body ready for repair objective: To synthesize new derivatives as anti-inflammatory and antioxidant agents. method: In first step chalcones (I1-I6) was obtained and in the second step, these chalcones were reacted with urea and thiourea in the presence of potassium hydroxide to obtain the corresponding pyrimidinones and thiopyrimidinones. The structures of the synthesized compounds 4-(substituted phenyl)-6-(substituted phenylamino)-3,4-dihydropyrimidine-2(1H)-ones/thione derivatives are investigated by means of TLC (visualized it in Iodine chamber), IR, mass, 1H-NMR spectral and elemental analysis. The title compounds evaluated for anti-inflammatory as well as antioxidant activity. Anti-inflammatory activity in vivo was carried out by carrageenan induced rat-paw edema method and compared with standard drug diclofenac sodium and antioxidant activity was measured by DPPH, FRAP and Hydrogen peroxide (H2O2) method and compared with standard ascorbic acid. result: Electron donating groups showed better antioxidant activity as compared to electron withdrawing ones in both activities. All the compounds exhibited good to moderate activity. Compound DHPM8 shows better antioxidant activity and compound DHPM6 shows better anti-inflammatory activity while compound DHPM11 shows minimum antioxidant as well as anti-inflammatory activity than other compounds. conclusion: To better understanding, we have performed molecular docking simulation. The molecular docking studies revealed that all synthesized compound were showed good receptor binding interaction in which compound 9 had highest docking score of 9.8 due to interaction with CYS36, PRO153, TYR130, GLY45, LEU152, ARG469, LYS468 and GLU465. other: NA","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"37 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142265003","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-18DOI: 10.2174/0113852728326804240828071148
Vladimir A. Potapov, Roman S. Ishigeev, Lyudmila A. Belovezhets, Svetlana V. Amosova
The synthesis of a novel family selenazolo[3,2-a]pyridin-4-ium derivatives in high yields was developed based on the annulation reactions of 2-pyridineselenenyl chloride with unsaturated heteroatom and heterocyclic compounds. The analogous new thiazolo[3,2-a]pyridin-4-ium derivatives were obtained by the annulation reactions of 2-pyridinesulfenyl chloride. The reactions with vinylic ethers and N-vinylimidazole gave 3- substituted selenazolo[3,2-a]- and -[1,3]thiazolopyridin-4-ium derivatives, whereas reactions with allyl alcohol, allyl chloride, allyl bromide, 3-butenoic, 4-pentenoic and 5-hexenoic acids occurred with the opposite regiochemistry, affording 2-substituted [1,3]chalcogenazolo[3,2-a]pyridiniums. The antibacterial activity of the obtained products against gram-positive and gram-negative bacteria was evaluated, and compounds with high activity were discovered. A comparison of the antibacterial properties of [1,3]selenazolo[3,2-a]pyridin-4-ium derivatives with their sulfur analogs shows a higher activity of the selenium compounds.
{"title":"A Novel Family of Selenazolo[3,2-a]pyridinium Derivatives Based on Annulation Reactions and Comparative Analysis of Antimicrobial Activity of the Selenium and Sulfur Analogs of Chalcogenazolo[3,2-a]pyridiniums","authors":"Vladimir A. Potapov, Roman S. Ishigeev, Lyudmila A. Belovezhets, Svetlana V. Amosova","doi":"10.2174/0113852728326804240828071148","DOIUrl":"https://doi.org/10.2174/0113852728326804240828071148","url":null,"abstract":"The synthesis of a novel family selenazolo[3,2-a]pyridin-4-ium derivatives in high yields was developed based on the annulation reactions of 2-pyridineselenenyl chloride with unsaturated heteroatom and heterocyclic compounds. The analogous new thiazolo[3,2-a]pyridin-4-ium derivatives were obtained by the annulation reactions of 2-pyridinesulfenyl chloride. The reactions with vinylic ethers and N-vinylimidazole gave 3- substituted selenazolo[3,2-a]- and -[1,3]thiazolopyridin-4-ium derivatives, whereas reactions with allyl alcohol, allyl chloride, allyl bromide, 3-butenoic, 4-pentenoic and 5-hexenoic acids occurred with the opposite regiochemistry, affording 2-substituted [1,3]chalcogenazolo[3,2-a]pyridiniums. The antibacterial activity of the obtained products against gram-positive and gram-negative bacteria was evaluated, and compounds with high activity were discovered. A comparison of the antibacterial properties of [1,3]selenazolo[3,2-a]pyridin-4-ium derivatives with their sulfur analogs shows a higher activity of the selenium compounds.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"2 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142265001","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-10DOI: 10.2174/0113852728322595240819045039
Manijeh Nematpour
: In this study, functionalized 2-(trichloromethyl)-1H-benzo[d]imidazole derivative with good yields was synthesized using a copper-catalyzed N-arylation reaction of 2-iodoaniline and trichloroacetonitrile. This reaction was performed by employing the catalytic value of copper (I) and 1,10-phenanthroline as the ligand in tetrahydrofuran solvent at 23°C. In the following, the reaction of the final product with phenylacetylene and sodium azide (Huisgen reaction) using the copper catalyst in water solvent at 23°C led to the synthesis of new (1,2,3-triazol)-1H-benzo[d]imidazole derivatives with the principles of green chemistry and suitable efficiency. The availability of raw materials and suitable catalysts, mild reaction conditions, and easy purification are among the advantages of this method for the synthesis of various multi-substituted benzo[d]imidazole and 1,2,3-triazole derivatives.
{"title":"A New Route for the Synthesis of Trichloromethyl-1H-Benzo[d]imidazole and (1,2,3- Triazol)-1H-Benzo[d]imidazole Derivatives via Copper-Catalyzed N-Arylation and Huisgen Reactions","authors":"Manijeh Nematpour","doi":"10.2174/0113852728322595240819045039","DOIUrl":"https://doi.org/10.2174/0113852728322595240819045039","url":null,"abstract":": In this study, functionalized 2-(trichloromethyl)-1H-benzo[d]imidazole derivative with good yields was synthesized using a copper-catalyzed N-arylation reaction of 2-iodoaniline and trichloroacetonitrile. This reaction was performed by employing the catalytic value of copper (I) and 1,10-phenanthroline as the ligand in tetrahydrofuran solvent at 23°C. In the following, the reaction of the final product with phenylacetylene and sodium azide (Huisgen reaction) using the copper catalyst in water solvent at 23°C led to the synthesis of new (1,2,3-triazol)-1H-benzo[d]imidazole derivatives with the principles of green chemistry and suitable efficiency. The availability of raw materials and suitable catalysts, mild reaction conditions, and easy purification are among the advantages of this method for the synthesis of various multi-substituted benzo[d]imidazole and 1,2,3-triazole derivatives.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"274 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142214509","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-10DOI: 10.2174/0113852728323915240816093254
Santanu Chakravorty
: Palladium-catalyzed reactions are widely used for creating carbon-carbon and carbon-heteroatom bonds, with the Heck reaction being particularly valuable for forming rings of various sizes, including mediumsized rings. Recent reports have shown the synthetic potential of intramolecular Heck reactions for assembling rings of seven or more members. While the regioselectivity of this cyclization is often unpredictable in the absence of directing groups, the reductive Heck cyclization strategy can help minimize this issue. Nickel catalysts are also valuable due to their abundance and environmentally friendly nature, playing a pivotal role in producing biologically significant carbocycles and heterocycles. The use of both Pd(0) and Ni(0) catalysts, with or without chiral ligands, has been successful in forming five to nine-member ring heterocycles and carbocycles in a simple, cost-effective manner. This review provides a comprehensive survey of the literature from the past decade on the use of reductive Heck cyclization methodology, including mechanistic details as needed.
{"title":"Recent Advance in the Reductive Heck Cyclization for the Formation of Five to Nine Member Rings","authors":"Santanu Chakravorty","doi":"10.2174/0113852728323915240816093254","DOIUrl":"https://doi.org/10.2174/0113852728323915240816093254","url":null,"abstract":": Palladium-catalyzed reactions are widely used for creating carbon-carbon and carbon-heteroatom bonds, with the Heck reaction being particularly valuable for forming rings of various sizes, including mediumsized rings. Recent reports have shown the synthetic potential of intramolecular Heck reactions for assembling rings of seven or more members. While the regioselectivity of this cyclization is often unpredictable in the absence of directing groups, the reductive Heck cyclization strategy can help minimize this issue. Nickel catalysts are also valuable due to their abundance and environmentally friendly nature, playing a pivotal role in producing biologically significant carbocycles and heterocycles. The use of both Pd(0) and Ni(0) catalysts, with or without chiral ligands, has been successful in forming five to nine-member ring heterocycles and carbocycles in a simple, cost-effective manner. This review provides a comprehensive survey of the literature from the past decade on the use of reductive Heck cyclization methodology, including mechanistic details as needed.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"97 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142214513","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-10DOI: 10.2174/0113852728322422240816060345
Ravi Varala, Murali Mohan Achari Kamsali, Ramanaiah S, Mohammed Mujahid Alam
: Di-tert-butyl peroxide (DTBP) is one of the most widely used organic peroxides in a variety of oxidative transformations. The main factors contributing to the increasing use of DTBP are its affordability, minimal environmental impact, great effectiveness, and capacity to substitute scarce or dangerous heavy metal oxidants. We have reviewed critically and succinctly the noteworthy applications of DTBP in heterocyclic ring constructions from 2014 onwards in this decennial update. The main components of this evaluation are the pros and cons of its use, the scope of a synthetic organic transformation, and mechanistic logistics.
{"title":"Di-tert-butyl Peroxide (DTBP)-Promoted Heterocyclic Ring Construction","authors":"Ravi Varala, Murali Mohan Achari Kamsali, Ramanaiah S, Mohammed Mujahid Alam","doi":"10.2174/0113852728322422240816060345","DOIUrl":"https://doi.org/10.2174/0113852728322422240816060345","url":null,"abstract":": Di-tert-butyl peroxide (DTBP) is one of the most widely used organic peroxides in a variety of oxidative transformations. The main factors contributing to the increasing use of DTBP are its affordability, minimal environmental impact, great effectiveness, and capacity to substitute scarce or dangerous heavy metal oxidants. We have reviewed critically and succinctly the noteworthy applications of DTBP in heterocyclic ring constructions from 2014 onwards in this decennial update. The main components of this evaluation are the pros and cons of its use, the scope of a synthetic organic transformation, and mechanistic logistics.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"59 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142214508","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-06DOI: 10.2174/0113852728331472240826071320
Ashraf A. Aly, Hisham A. Abd El-Naby, Essam Kh. Ahmed, Sageda A. Gedamy, Mohammed B. Alshammari, Akil Ahmed, Stefan Braese
: Pyrano[3,2-c]quinolone and pyrano[2,3-c]quinoline, as promising molecules, have garnered more attention due to their interesting biological properties. This review dealt with the catalytic synthesis of the former candidates in the last 20 years. Multi-component reactions (MCRs) are synthetic routes that produce a single product from three or more reactants in a one-pot step procedure. We herein reported on the advantages of catalysis in synthesizing the target compounds using the MCR sequence. We also discussed the mechanism and explained the chosen catalyst's utility in the target molecules' selectivity. Finally, this recent review focuses on the biological applications of these molecules as anticancer, antimicrobial activities, anti-diabetic, antiinflammatory, anti-Alzheimer, and antitubercular agents.
{"title":"Catalytic Syntheses of Pyrano[3,2-C]Quinolone and -Quinoline Derivatives and their Potential Therapeutic Agents","authors":"Ashraf A. Aly, Hisham A. Abd El-Naby, Essam Kh. Ahmed, Sageda A. Gedamy, Mohammed B. Alshammari, Akil Ahmed, Stefan Braese","doi":"10.2174/0113852728331472240826071320","DOIUrl":"https://doi.org/10.2174/0113852728331472240826071320","url":null,"abstract":": Pyrano[3,2-c]quinolone and pyrano[2,3-c]quinoline, as promising molecules, have garnered more attention due to their interesting biological properties. This review dealt with the catalytic synthesis of the former candidates in the last 20 years. Multi-component reactions (MCRs) are synthetic routes that produce a single product from three or more reactants in a one-pot step procedure. We herein reported on the advantages of catalysis in synthesizing the target compounds using the MCR sequence. We also discussed the mechanism and explained the chosen catalyst's utility in the target molecules' selectivity. Finally, this recent review focuses on the biological applications of these molecules as anticancer, antimicrobial activities, anti-diabetic, antiinflammatory, anti-Alzheimer, and antitubercular agents.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"6 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142214512","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-04DOI: 10.2174/0113852728316820240815164622
Sheersha Pradhan, Banoth Janhavi, Thangamuthu Mohan Das
Due to the compatibility of binding and undergoing chemical modification of sugar derivatives with a variety of scaffolds, the design of innovative tools for bio-sensing and bio-marking, energy harvesting, drug design, and delivery is growing steadily. Furthermore, the chemistry of partially protected sugars has not been explored well in terms of its applications in smart materials. However, these sugar derivatives possess a unique characteristic balance between hydrophilic and hydrophobic nature, which makes them act as gelator molecules. Several synthetic strategies pertaining to synthesis and applications are known in the literature. The present review mainly focuses on the partially protected monosaccharide-based N-glycosylamines and their applications, with few examples from O- and C-glycosides.
{"title":"Recent Advances in the Synthesis and Applications of Partially Protected N-Glycosylamines","authors":"Sheersha Pradhan, Banoth Janhavi, Thangamuthu Mohan Das","doi":"10.2174/0113852728316820240815164622","DOIUrl":"https://doi.org/10.2174/0113852728316820240815164622","url":null,"abstract":"Due to the compatibility of binding and undergoing chemical modification of sugar derivatives with a variety of scaffolds, the design of innovative tools for bio-sensing and bio-marking, energy harvesting, drug design, and delivery is growing steadily. Furthermore, the chemistry of partially protected sugars has not been explored well in terms of its applications in smart materials. However, these sugar derivatives possess a unique characteristic balance between hydrophilic and hydrophobic nature, which makes them act as gelator molecules. Several synthetic strategies pertaining to synthesis and applications are known in the literature. The present review mainly focuses on the partially protected monosaccharide-based N-glycosylamines and their applications, with few examples from O- and C-glycosides.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"2 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-09-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142214510","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
: This review summarizes the recent trends in the transition-metal-catalyzed C-H bond functionalization approach to access C-branched (hetero)aryl/alkenyl/alkyl glycosides with reaction characteristics and proposed mechanisms. Recently, the Transition-metal-catalyzed C-H functionalization has arisen as a groundbreaking and versatile method for producing potent C-branched glycosides feasibly and efficiently. Nowadays, site-selective functionalization of C-H bonds in carbohydrate chemistry is highly demanded, owing to the intricate and highly stable nature of C-H bonds. In this context, we systematically summarize the C-H glycosylation of arenes, C-H arylation of glycoside, and Cattelani-strategy with mechanistic investigation. Also, the applications of transition-metal-catalyzed C-glycosylation for the formation of biologically active molecules are discussed.
{"title":"Emerging Advances in Transition Metal-Catalyzed C-H Bond Functionalizations Towards C-Glycosides","authors":"Zanjila Azeem, Sunny Maurya, Mohammad Ovais, Rekha Sagwan, Atul Dubey, Pintu Kumar Mandal","doi":"10.2174/0113852728326485240815110646","DOIUrl":"https://doi.org/10.2174/0113852728326485240815110646","url":null,"abstract":": This review summarizes the recent trends in the transition-metal-catalyzed C-H bond functionalization approach to access C-branched (hetero)aryl/alkenyl/alkyl glycosides with reaction characteristics and proposed mechanisms. Recently, the Transition-metal-catalyzed C-H functionalization has arisen as a groundbreaking and versatile method for producing potent C-branched glycosides feasibly and efficiently. Nowadays, site-selective functionalization of C-H bonds in carbohydrate chemistry is highly demanded, owing to the intricate and highly stable nature of C-H bonds. In this context, we systematically summarize the C-H glycosylation of arenes, C-H arylation of glycoside, and Cattelani-strategy with mechanistic investigation. Also, the applications of transition-metal-catalyzed C-glycosylation for the formation of biologically active molecules are discussed.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142214519","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-08-29DOI: 10.2174/0113852728315680240815095102
Dnyaneshwar D. Subhedar, Mubarak H. Shaikh, Amol A. Nagargoje, Dhiman Sarkar, Vijay M. Khedkar, Bapurao B. Shingate
Here, we report the solvent-free one-pot multicomponent synthesis of 4-substituted-1,5- benzodiazepine derivatives from O-phenylenediamine, aromatic aldehydes, and dimedone using [DBUH][HSO4] as a catalyst in excellent yields. This process was carried out in search of a reusable, easily accessible, affordable, and efficient catalyst. 1,5-Benzodiazepines demonstrate a new family of good inhibitors with potent anti-mycobacterial properties. The most promising compounds in the present series are 4c, 4i, and 4l which showed excellent activity and inhibited the growth of both MTB H37Ra and M. bovis BCG strains with lower MICs. The most active compounds were further studied for their cytotoxicity against cell lines MCF-7, A549, HCT116, and THP-1 by MTT assays and the compounds were found to be non-toxic. The fact that none of these compounds work against either Gram-positive or Gram-negative bacteria suggests that they are only effective against MTB. The in silico docking of the molecules against mycobacterial enoyl reductase, InhA enzyme could provide well-clustered solutions and have given valuable insights into the thermodynamic elements governing the binding affinities. The findings of this investigation unmistakably point to the discovery of extremely specific and selective MTB inhibitors, which can now be investigated further in search of possible anti-tubercular drugs.
{"title":"[DBUH][HSO4]-Catalyzed Solvent-Free Synthesis of 1,5-Benzodiazepine Derivatives: Bioevaluation and In Silico Molecular Docking Study","authors":"Dnyaneshwar D. Subhedar, Mubarak H. Shaikh, Amol A. Nagargoje, Dhiman Sarkar, Vijay M. Khedkar, Bapurao B. Shingate","doi":"10.2174/0113852728315680240815095102","DOIUrl":"https://doi.org/10.2174/0113852728315680240815095102","url":null,"abstract":"Here, we report the solvent-free one-pot multicomponent synthesis of 4-substituted-1,5- benzodiazepine derivatives from O-phenylenediamine, aromatic aldehydes, and dimedone using [DBUH][HSO4] as a catalyst in excellent yields. This process was carried out in search of a reusable, easily accessible, affordable, and efficient catalyst. 1,5-Benzodiazepines demonstrate a new family of good inhibitors with potent anti-mycobacterial properties. The most promising compounds in the present series are 4c, 4i, and 4l which showed excellent activity and inhibited the growth of both MTB H37Ra and M. bovis BCG strains with lower MICs. The most active compounds were further studied for their cytotoxicity against cell lines MCF-7, A549, HCT116, and THP-1 by MTT assays and the compounds were found to be non-toxic. The fact that none of these compounds work against either Gram-positive or Gram-negative bacteria suggests that they are only effective against MTB. The in silico docking of the molecules against mycobacterial enoyl reductase, InhA enzyme could provide well-clustered solutions and have given valuable insights into the thermodynamic elements governing the binding affinities. The findings of this investigation unmistakably point to the discovery of extremely specific and selective MTB inhibitors, which can now be investigated further in search of possible anti-tubercular drugs.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"41 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-08-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142214514","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
京公网安备 11010802042870号
京ICP备2023020795号-1
扫码关注我们
求助内容：
应助结果提醒方式：