Pub Date : 2023-09-30DOI: 10.59467/ijhc.2023.33.385
Nigam Jyoti Maiti, Swastika Ganguly
A series of new substituted phenyl-2-(perchloro-1H-benzo[d][1,2,3]triazol-1-yl)ethan-1-one derivatives 3(a-j) was synthesized, and evaluated for antimycobacterial and antimicrobial activity. Among all the tested compounds, compound 3h exhibited the highest antimycobacterial and antibacterial activity, comparable to the standard drug. Finally, the binding mode analysis of the highly active compounds was performed in the active binding site, the co-crystallized structure of Mycobacterium tuberculosis (PDB ID 2×22) and glucosamine-6-phosphate synthase (PDB ID 2VF5).
合成了一系列新的取代苯-2-(高氯- 1h -苯并[d][1,2,3]三唑-1-基)乙二酮衍生物3(A -j)，并对其抑菌活性和抗菌活性进行了评价。在所有被测化合物中，化合物3h表现出最高的抑菌活性，与标准药物相当。最后，在结核分枝杆菌(PDB ID 2×22)和葡萄糖胺-6-磷酸合酶(PDB ID 2VF5)的活性结合位点共结晶结构上对高活性化合物进行结合模式分析。
{"title":"Some New Benzotriazole Derivatives: Synthesis, Antimycobacterial Evaluation, Antimicrobial Efficacy, ADME Studies, and Molecular Docking Studies","authors":"Nigam Jyoti Maiti, Swastika Ganguly","doi":"10.59467/ijhc.2023.33.385","DOIUrl":"https://doi.org/10.59467/ijhc.2023.33.385","url":null,"abstract":"A series of new substituted phenyl-2-(perchloro-1H-benzo[d][1,2,3]triazol-1-yl)ethan-1-one derivatives 3(a-j) was synthesized, and evaluated for antimycobacterial and antimicrobial activity. Among all the tested compounds, compound 3h exhibited the highest antimycobacterial and antibacterial activity, comparable to the standard drug. Finally, the binding mode analysis of the highly active compounds was performed in the active binding site, the co-crystallized structure of Mycobacterium tuberculosis (PDB ID 2×22) and glucosamine-6-phosphate synthase (PDB ID 2VF5).","PeriodicalId":54993,"journal":{"name":"Indian Journal of Heterocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135038082","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 : 2023-09-30DOI: 10.59467/ijhc.2023.33.349
Shivam Joshi, Neha Kawathekar
A new series of N-benzylindolylchalcone analogs has been designed, synthesized, and screened for in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv. The synthesis of N-benzylatedindole-3-carbaldehyde derivatives, namely, -1-(2-methylbenzyl)-1H-indole-3-carbaldehyde (S2I1)1-(3-methylbenzyl)-1Hindole-3-carbaldehyde (S2I2), was achieved by N-benzylation of indole-3-carbaldehyde using a mixture of different bases in DMF. Subsequent condensation of these derivatives with various acetophenones led to the synthesis of the corresponding N-benzylindolylchalcone derivatives. Notably, within this series of compounds,(E)-1-(4-fluorophenyl)-3-(1-(2-methylbenzyl)-1H-indol-3-yl)prop-2-en-1-one (S2R1) and (E)-1-(4-hydroxyphenyl)-3-(1-(3-methylbenzyl)- 1H-indol-3-yl)prop-2-en-1-one (S2R11) exhibited remarkable antitubercular activity, demonstrating minimal inhibitory concentrations values of 18 and 19 μg/mL, respectively.
{"title":"Synthesis and Biological Evaluation of N-Benzylindolylchalcone Analogs as Antitubercular Agents","authors":"Shivam Joshi, Neha Kawathekar","doi":"10.59467/ijhc.2023.33.349","DOIUrl":"https://doi.org/10.59467/ijhc.2023.33.349","url":null,"abstract":"A new series of N-benzylindolylchalcone analogs has been designed, synthesized, and screened for in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv. The synthesis of N-benzylatedindole-3-carbaldehyde derivatives, namely, -1-(2-methylbenzyl)-1H-indole-3-carbaldehyde (S2I1)1-(3-methylbenzyl)-1Hindole-3-carbaldehyde (S2I2), was achieved by N-benzylation of indole-3-carbaldehyde using a mixture of different bases in DMF. Subsequent condensation of these derivatives with various acetophenones led to the synthesis of the corresponding N-benzylindolylchalcone derivatives. Notably, within this series of compounds,(E)-1-(4-fluorophenyl)-3-(1-(2-methylbenzyl)-1H-indol-3-yl)prop-2-en-1-one (S2R1) and (E)-1-(4-hydroxyphenyl)-3-(1-(3-methylbenzyl)- 1H-indol-3-yl)prop-2-en-1-one (S2R11) exhibited remarkable antitubercular activity, demonstrating minimal inhibitory concentrations values of 18 and 19 μg/mL, respectively.","PeriodicalId":54993,"journal":{"name":"Indian Journal of Heterocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135038092","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 : 2023-09-30DOI: 10.59467/ijhc.2023.33.311
Mary Nygi, L. Aruna Priya, Shalini Devi, B. Prashanthi, S. Kalyani
A series of ten new pyrimidinedione derivatives (4a-j) was synthesized from a common scaffold, 1-(((benzyloxy) carbonyl)methyl)-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carboxylic acid (2). The compound (2) was subjected to acid– amine coupling with different amines 3(a-j). The coupling reaction was performed using HATU as a coupling reagent at room temperature for 3h using the base N-methylmorpholine and solvent DMF. The desired derivatives were obtained with good yields. The synthesized compound’s purity was determined by HPLC analytical techniques. The structures of the pyrimidinediones were analyzed by Fourier-transform infrared spectroscopy, proton nuclear magnetic resonance (1H NMR), 13C NMR, liquid chromatography–mass spectrometry, and Human Resource Management System data. All ten amide derivatives were tested for antibacterial efficacy using Staphylococcus aureus (Gram-positive strain bacteria) and Pseudomonas putida (Gram-negative strain bacteria). Compounds 4g as well as 4h showed significant antibacterial effectiveness, with good minimum inhibition concentration values. A molecular docking study was also performed with the protein 3FQO selected from the Protein Data Bank. The amide compounds 4g and 4h displayed good docking scores. The results of the in silico study complemented the antibacterial effectiveness of the two analogs 4g and 4h. The presence of electron donating groups in these target molecules may be attributed to their high efficacy.
{"title":"Synthesis and Antibacterial Activity of New Amide Derivatives of Pyrimidinediones","authors":"Mary Nygi, L. Aruna Priya, Shalini Devi, B. Prashanthi, S. Kalyani","doi":"10.59467/ijhc.2023.33.311","DOIUrl":"https://doi.org/10.59467/ijhc.2023.33.311","url":null,"abstract":"A series of ten new pyrimidinedione derivatives (4a-j) was synthesized from a common scaffold, 1-(((benzyloxy) carbonyl)methyl)-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carboxylic acid (2). The compound (2) was subjected to acid– amine coupling with different amines 3(a-j). The coupling reaction was performed using HATU as a coupling reagent at room temperature for 3h using the base N-methylmorpholine and solvent DMF. The desired derivatives were obtained with good yields. The synthesized compound’s purity was determined by HPLC analytical techniques. The structures of the pyrimidinediones were analyzed by Fourier-transform infrared spectroscopy, proton nuclear magnetic resonance (1H NMR), 13C NMR, liquid chromatography–mass spectrometry, and Human Resource Management System data. All ten amide derivatives were tested for antibacterial efficacy using Staphylococcus aureus (Gram-positive strain bacteria) and Pseudomonas putida (Gram-negative strain bacteria). Compounds 4g as well as 4h showed significant antibacterial effectiveness, with good minimum inhibition concentration values. A molecular docking study was also performed with the protein 3FQO selected from the Protein Data Bank. The amide compounds 4g and 4h displayed good docking scores. The results of the in silico study complemented the antibacterial effectiveness of the two analogs 4g and 4h. The presence of electron donating groups in these target molecules may be attributed to their high efficacy.","PeriodicalId":54993,"journal":{"name":"Indian Journal of Heterocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135038275","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 : 2023-09-30DOI: 10.59467/ijhc.2023.33.293
Priyanka Chandra, Swastika Swastika, Manik Ghosh
Human immunodeficiency virus-1 (HIV-1) reverse transcriptase enzyme catalyzes the conversion of viral RNA to DNA. This viral DNA infects a healthy host body, it leads to the production of viral DNA in higher concentrations and leads to a disease called acquired immunodeficiency syndrome; which is a very fatal disease and leads to the development of several other diseases. Therefore, the development of effective inhibitors is required to execute the therapeutic effects against this disease. In this context, in the present study, the docking studies of compounds showing HIV-1 inhibition were performed in the non-nucleoside reverse transcriptase inhibitory binding pocket of the enzyme HIV-1 reverse transcriptase (protein data bank [PDB] ID-1RT2), using AutoDock 4.2.6 and to identify the important pharmacophoric features required for the development of effective non-nucleoside reverse transcriptase inhibitors, pharmacophore analysis was performed. The findings of this study can be used as a valuable tool for identifying and developing potent and effective inhibitors.
人类免疫缺陷病毒-1 (HIV-1)逆转录酶催化病毒RNA转化为DNA。这种病毒DNA感染了健康的宿主身体，导致病毒DNA浓度升高导致获得性免疫缺陷综合症;这是一种非常致命的疾病，并会导致其他几种疾病的发展。因此，需要开发有效的抑制剂来实现对该疾病的治疗效果。在此背景下，本研究在HIV-1逆转录酶的非核苷类逆转录酶抑制结合袋(protein data bank [PDB] ID-1RT2)中对具有HIV-1抑制作用的化合物进行对接研究，使用AutoDock 4.2.6进行对接研究，并确定开发有效的非核苷类逆转录酶抑制剂所需的重要药效特征，进行药效团分析。本研究结果可作为鉴定和开发有效抑制剂的宝贵工具。
{"title":"In Silico Studies of Piperazinyl-4-Nitroimidazole Derivatives in the Non-Nucleoside Inhibitory Binding Pocket of Human Immunodeficiency Virus-1-Reverse Transcriptase Enzyme","authors":"Priyanka Chandra, Swastika Swastika, Manik Ghosh","doi":"10.59467/ijhc.2023.33.293","DOIUrl":"https://doi.org/10.59467/ijhc.2023.33.293","url":null,"abstract":"Human immunodeficiency virus-1 (HIV-1) reverse transcriptase enzyme catalyzes the conversion of viral RNA to DNA. This viral DNA infects a healthy host body, it leads to the production of viral DNA in higher concentrations and leads to a disease called acquired immunodeficiency syndrome; which is a very fatal disease and leads to the development of several other diseases. Therefore, the development of effective inhibitors is required to execute the therapeutic effects against this disease. In this context, in the present study, the docking studies of compounds showing HIV-1 inhibition were performed in the non-nucleoside reverse transcriptase inhibitory binding pocket of the enzyme HIV-1 reverse transcriptase (protein data bank [PDB] ID-1RT2), using AutoDock 4.2.6 and to identify the important pharmacophoric features required for the development of effective non-nucleoside reverse transcriptase inhibitors, pharmacophore analysis was performed. The findings of this study can be used as a valuable tool for identifying and developing potent and effective inhibitors.","PeriodicalId":54993,"journal":{"name":"Indian Journal of Heterocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135038254","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 : 2023-09-30DOI: 10.59467/ijhc.2023.33.361
Geeta Mishra, Parmesh K. Dwivedi, Neeraj Verma, Sajal Srivastava, Ashok K. Singh, Devdutt Chaturvedi
A new series of thiophene hybridized thiadiazolyl Schiff bases was designed and synthesized employing FeCl3-mediated cyclization of thiosemicarbazoneinto thiadiazoles and their subsequent Schiff bases formation using p-TSA in benzene. To understand the interaction of the proposed compounds with β-lactamase (Protein Data Bank [PDB] ID: 3UDI), a molecular docking was performed. All the compounds demonstrated an optimal binding affinity with β-lactamase (−8.17 to −9.75 kcal/mol) and showed crucial hydrogen bonds and π–π interaction with the leading amino acids Arg298, Ala300, and Val391 located at the active site of β-lactamase. The in vitro antibacterial activity of the desired molecules was conducted against few gram-positive and Gram-negative bacterial strains using amoxicillinas reference drug. The compound having p-hydroxyphenyl substituent (3c) was found to be potentially effective to inhibit P. aeruginosa and E. coli with MIC value 7.5 μg/mL and 9.0 μg/mL, respectively, whereas other compounds exhibited moderate to good activity. Altogether, the primary in-vitro screening of newly synthesized thiophene hybridized thiadiazole Schiff bases opens a new venture towards the development of promising alternatives of β-lactamase inhibitors as anti-bacterial agents.
设计并合成了一系列新的噻吩杂化噻二唑希夫碱，采用fec13介导的硫代氨基脲环化制备噻二唑，并在苯中利用对- tsa形成噻二唑希夫碱。为了了解所提出的化合物与β-内酰胺酶(Protein Data Bank [PDB] ID: 3UDI)的相互作用，进行了分子对接。所有化合物均与β-内酰胺酶表现出最佳的结合亲和力(−8.17 ~−9.75 kcal/mol)，并与β-内酰胺酶活性位点的氨基酸Arg298、Ala300和Val391表现出关键的氢键和π -π相互作用。利用阿莫西林纳参比药对几种革兰氏阳性和革兰氏阴性菌株进行体外抑菌活性研究。含有对羟基苯基取代基(3c)的化合物对铜绿假单胞菌和大肠杆菌具有潜在的抑制作用，MIC值分别为7.5 μg/mL和9.0 μg/mL，而其他化合物的抑制活性为中等至良好。总之，新合成的噻吩杂化噻二唑希夫碱的初步体外筛选为开发β-内酰胺酶抑制剂作为抗菌药物的有前途的替代品开辟了新的道路。
{"title":"p-TSA-Promoted Efficient Synthesis of Some New Thiophene Hybridized Thiadiazolyl Schiff Bases as Antibacterial Agents","authors":"Geeta Mishra, Parmesh K. Dwivedi, Neeraj Verma, Sajal Srivastava, Ashok K. Singh, Devdutt Chaturvedi","doi":"10.59467/ijhc.2023.33.361","DOIUrl":"https://doi.org/10.59467/ijhc.2023.33.361","url":null,"abstract":"A new series of thiophene hybridized thiadiazolyl Schiff bases was designed and synthesized employing FeCl3-mediated cyclization of thiosemicarbazoneinto thiadiazoles and their subsequent Schiff bases formation using p-TSA in benzene. To understand the interaction of the proposed compounds with β-lactamase (Protein Data Bank [PDB] ID: 3UDI), a molecular docking was performed. All the compounds demonstrated an optimal binding affinity with β-lactamase (−8.17 to −9.75 kcal/mol) and showed crucial hydrogen bonds and π–π interaction with the leading amino acids Arg298, Ala300, and Val391 located at the active site of β-lactamase. The in vitro antibacterial activity of the desired molecules was conducted against few gram-positive and Gram-negative bacterial strains using amoxicillinas reference drug. The compound having p-hydroxyphenyl substituent (3c) was found to be potentially effective to inhibit P. aeruginosa and E. coli with MIC value 7.5 μg/mL and 9.0 μg/mL, respectively, whereas other compounds exhibited moderate to good activity. Altogether, the primary in-vitro screening of newly synthesized thiophene hybridized thiadiazole Schiff bases opens a new venture towards the development of promising alternatives of β-lactamase inhibitors as anti-bacterial agents.","PeriodicalId":54993,"journal":{"name":"Indian Journal of Heterocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135038267","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 : 2023-09-30DOI: 10.59467/ijhc.2023.33.331
Khushal M. Kapadiya, Marupati Siddhartha, Kalpesh S. Parikh, Deepkumar S. Joshi, Jayesh Dhalani, Piyush V. Dholaria
In search of suitable antimicrobial compounds, we report here the synthesis, characterization, and biological activities of 2-((5-(2-nitrophenyl)-1,3,4-oxadiazol-2-yl)thio)-N-arylacetamide (5a-5p). The molecules were characterized by infrared, mass, hydrogen-1 nuclear magnetic resonance (1H NMR), 13C NMR, and elemental analysis. The in vitro antimicrobial activity was investigated against pathogenic Gram-positive and Gram-negative bacterial and fungal strains. The results were explained with a molecular docking study against microbial DNA gyrase. It was found that the compounds 5h, 5i, 5j, 5k, 5l, 5n, and 5p showed significant activities against tested organisms as compared to standard drugs (fluconazole and ciprofloxacin).
为了寻找合适的抗菌化合物，我们在这里报道了2-((5-(2-硝基苯基)-1,3,4-恶二唑-2-基)硫代)- n -芳基乙酰胺(5a-5p)的合成、表征和生物活性。通过红外、质量、氢-1核磁共振(1H NMR)、13C核磁共振(13C NMR)和元素分析对分子进行了表征。研究了其对致病性革兰氏阳性和革兰氏阴性细菌和真菌的体外抑菌活性。结果与微生物DNA回转酶的分子对接研究解释。与标准药物(氟康唑和环丙沙星)相比，化合物5h、5i、5j、5k、5l、5n和5p对被试生物具有显著的活性。
{"title":"Design, Synthesis, and Molecular Docking Studies of 1,3,4-Oxadiazole Scaffolds as Potential Antimicrobial Agents","authors":"Khushal M. Kapadiya, Marupati Siddhartha, Kalpesh S. Parikh, Deepkumar S. Joshi, Jayesh Dhalani, Piyush V. Dholaria","doi":"10.59467/ijhc.2023.33.331","DOIUrl":"https://doi.org/10.59467/ijhc.2023.33.331","url":null,"abstract":"In search of suitable antimicrobial compounds, we report here the synthesis, characterization, and biological activities of 2-((5-(2-nitrophenyl)-1,3,4-oxadiazol-2-yl)thio)-N-arylacetamide (5a-5p). The molecules were characterized by infrared, mass, hydrogen-1 nuclear magnetic resonance (1H NMR), 13C NMR, and elemental analysis. The in vitro antimicrobial activity was investigated against pathogenic Gram-positive and Gram-negative bacterial and fungal strains. The results were explained with a molecular docking study against microbial DNA gyrase. It was found that the compounds 5h, 5i, 5j, 5k, 5l, 5n, and 5p showed significant activities against tested organisms as compared to standard drugs (fluconazole and ciprofloxacin).","PeriodicalId":54993,"journal":{"name":"Indian Journal of Heterocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135038083","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 : 2023-09-30DOI: 10.59467/ijhc.2023.33.278
Praneetha Visampalli, Girija Sastry Vedula
A new series of 7-(arylidene/heteroylidene imino)-2-(3,4-dimethoxy-phenyl)-5-oxo-1,5-dihydro-[1,2,4] triazolo[1,5-α]pyridine-6-carbonitrile derivatives i.e., Schiff bases (4a-4j) was synthesized from reaction of 7-amino-2-(3,4-dimethoxy-phenyl)-5-oxo-1,5-dihydro-[1,2,4]triazolo[1,5-α]pyridine-6-carbonitrile (3) with substituted benzaldehydes or hetraldehydes in presence of glacial acetic acid. The antibacterial and anti-inflammatory properties of compounds 3, 4a-4j were investigated, and the results showed that some of the synthesized compounds had better activity than the standard reference drugs. The minimum inhibitory concentration of compounds 4b, 4c, 4f, 4g, and 4i was found to be 10 μg/mL, which was lower than that of ciprofloxacin. The compounds were also tested for anti-inflammatory properties in vitro, and compounds 4a and 4f were found to have superior anti-inflammatory action at 100 μg/mL compared to the standard reference drug ibuprofen.
{"title":"Synthesis of Some New 7-(arylidene/heteroylidene imino)-2-(3,4-dimethoxy-phenyl)-5-oxo- 1,5-dihydro-[1,2,4]triazolo[1,5-α]pyridine-6-carbonitrile Derivatives as Potent Antibacterial and Anti-inflammatory Agents","authors":"Praneetha Visampalli, Girija Sastry Vedula","doi":"10.59467/ijhc.2023.33.278","DOIUrl":"https://doi.org/10.59467/ijhc.2023.33.278","url":null,"abstract":"A new series of 7-(arylidene/heteroylidene imino)-2-(3,4-dimethoxy-phenyl)-5-oxo-1,5-dihydro-[1,2,4] triazolo[1,5-α]pyridine-6-carbonitrile derivatives i.e., Schiff bases (4a-4j) was synthesized from reaction of 7-amino-2-(3,4-dimethoxy-phenyl)-5-oxo-1,5-dihydro-[1,2,4]triazolo[1,5-α]pyridine-6-carbonitrile (3) with substituted benzaldehydes or hetraldehydes in presence of glacial acetic acid. The antibacterial and anti-inflammatory properties of compounds 3, 4a-4j were investigated, and the results showed that some of the synthesized compounds had better activity than the standard reference drugs. The minimum inhibitory concentration of compounds 4b, 4c, 4f, 4g, and 4i was found to be 10 μg/mL, which was lower than that of ciprofloxacin. The compounds were also tested for anti-inflammatory properties in vitro, and compounds 4a and 4f were found to have superior anti-inflammatory action at 100 μg/mL compared to the standard reference drug ibuprofen.","PeriodicalId":54993,"journal":{"name":"Indian Journal of Heterocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135038268","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 : 2023-09-30DOI: 10.59467/ijhc.2023.33.341
Ravikumar R. Makwana, Khushal M. Kapadiya, Jaysukhlal M. Parmar
A one-pot catalytic and column-free synthesis of fused imidazo[1,2-a]pyridines(4a-4j), from readily available pyridin-2-amine, various isocyanide, and tiglic aldehyde [2-methylbut-2-enal] as building blocks through the Groebke– Blackburn–Bienaymé reaction (GBBR) is reported. This efficient protocol has the advantages of environmental friendliness in terms of atom economy, high yields, and operational simplicity. The optimization of the process was carried out by various p and d block metal catalysts (particularly, Th(NO3)4, AlCl3, PCl3, La(NO3)3, Sc(OTf)3, ZrCl4, and SrCl2) and found most efficient with Zirconium metal catalyst. The biological evaluation demonstrated that compound 4a(t-butyl isocyanide) and 4h (cyclohexyl isocyanide) showed promising antioxidant activity concerning the used standard (ascorbic acid).
{"title":"Synthesis and Antioxidant Activity of Tiglic Aldehyde-Based Fused Imidazo[1,2-a]Pyridines: A Groebke–Blackburn–Bienaymé Reaction","authors":"Ravikumar R. Makwana, Khushal M. Kapadiya, Jaysukhlal M. Parmar","doi":"10.59467/ijhc.2023.33.341","DOIUrl":"https://doi.org/10.59467/ijhc.2023.33.341","url":null,"abstract":"A one-pot catalytic and column-free synthesis of fused imidazo[1,2-a]pyridines(4a-4j), from readily available pyridin-2-amine, various isocyanide, and tiglic aldehyde [2-methylbut-2-enal] as building blocks through the Groebke– Blackburn–Bienaymé reaction (GBBR) is reported. This efficient protocol has the advantages of environmental friendliness in terms of atom economy, high yields, and operational simplicity. The optimization of the process was carried out by various p and d block metal catalysts (particularly, Th(NO3)4, AlCl3, PCl3, La(NO3)3, Sc(OTf)3, ZrCl4, and SrCl2) and found most efficient with Zirconium metal catalyst. The biological evaluation demonstrated that compound 4a(t-butyl isocyanide) and 4h (cyclohexyl isocyanide) showed promising antioxidant activity concerning the used standard (ascorbic acid).","PeriodicalId":54993,"journal":{"name":"Indian Journal of Heterocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135038093","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 : 2023-09-30DOI: 10.59467/ijhc.2023.33.377
K. Mamatha, K. Sirisha, E. Venkateswarlu, B.S. Sharavanabhava
The 1,4-dihydropyridine derivatives (DHPs) (3a-b and 4a-c) were oxidized with iodine in methanol to produce five new, hitherto unreported pyridine derivatives (5a-b and 6a-c). The “Everted sac method” was used to assess the DHPs and their pyridines for potential p-glycoprotein (P-gp) inhibitory or multidrug resistance reversal action. Domperidone, a P-gp substrate, was examined for intestinal absorption in everted rat jejunal segments in the presence and absence of DHPs (3a-b and 4a-c) and pyridines (5a-b and 6a-c) at doses of 30 μg/mL and 100 μg/mL. The standard was Verapamil, a known P-gp inhibitor (30 μg/mL and 100 μg/mL). The P-gp inhibition of all the tested compounds was higher than Verapamil. The P-gp inhibition of compounds 5b and 6b was the highest. Utilizing isolated rat ileum, the newly synthesized pyridine derivatives calcium channel blocking efficacy was also investigated. The strongest Ca2+ channel-blocking action was seen with compound 5b. It was determined to be equivalent to Nifedipine, the gold standard. Strong P-gp inhibitor compound 6b has little calcium channel-blocking action.
{"title":"Synthesis and Evaluation of Some New Pyridines as Possible P-gp Inhibitors with Reduced Calcium Channel Blocking Activity","authors":"K. Mamatha, K. Sirisha, E. Venkateswarlu, B.S. Sharavanabhava","doi":"10.59467/ijhc.2023.33.377","DOIUrl":"https://doi.org/10.59467/ijhc.2023.33.377","url":null,"abstract":"The 1,4-dihydropyridine derivatives (DHPs) (3a-b and 4a-c) were oxidized with iodine in methanol to produce five new, hitherto unreported pyridine derivatives (5a-b and 6a-c). The “Everted sac method” was used to assess the DHPs and their pyridines for potential p-glycoprotein (P-gp) inhibitory or multidrug resistance reversal action. Domperidone, a P-gp substrate, was examined for intestinal absorption in everted rat jejunal segments in the presence and absence of DHPs (3a-b and 4a-c) and pyridines (5a-b and 6a-c) at doses of 30 μg/mL and 100 μg/mL. The standard was Verapamil, a known P-gp inhibitor (30 μg/mL and 100 μg/mL). The P-gp inhibition of all the tested compounds was higher than Verapamil. The P-gp inhibition of compounds 5b and 6b was the highest. Utilizing isolated rat ileum, the newly synthesized pyridine derivatives calcium channel blocking efficacy was also investigated. The strongest Ca2+ channel-blocking action was seen with compound 5b. It was determined to be equivalent to Nifedipine, the gold standard. Strong P-gp inhibitor compound 6b has little calcium channel-blocking action.","PeriodicalId":54993,"journal":{"name":"Indian Journal of Heterocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135038110","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 : 2023-09-30DOI: 10.59467/ijhc.2023.33.369
T. M. Somanatha, G. Krishnaswamy, R. Bhavana, K. Radhakrishna, G. Shivaraj, S. Sreenivasa, M. Shet Prakash
In the present investigation, we focused our interest to develop 1, 2, 3-triazolefuran chalcone hybrids along with their biological profile. The synthesis of target molecules involves sequence of reactions, namely diazotization, nucleophilic substitution, cycloaddition and finally, solvent-free Claisen–Schmidt condensation reaction. The biological profile of the synthesized compounds was carried out using prediction of activity spectra for substances and results revealed that the synthesized compounds may act as mild antimicrobial agents.
{"title":"Synthesis, In Vitro and In Silico Biological Studies of 1, 2, 3-Triazole-Furan Chalcone Hybrids","authors":"T. M. Somanatha, G. Krishnaswamy, R. Bhavana, K. Radhakrishna, G. Shivaraj, S. Sreenivasa, M. Shet Prakash","doi":"10.59467/ijhc.2023.33.369","DOIUrl":"https://doi.org/10.59467/ijhc.2023.33.369","url":null,"abstract":"In the present investigation, we focused our interest to develop 1, 2, 3-triazolefuran chalcone hybrids along with their biological profile. The synthesis of target molecules involves sequence of reactions, namely diazotization, nucleophilic substitution, cycloaddition and finally, solvent-free Claisen–Schmidt condensation reaction. The biological profile of the synthesized compounds was carried out using prediction of activity spectra for substances and results revealed that the synthesized compounds may act as mild antimicrobial agents.","PeriodicalId":54993,"journal":{"name":"Indian Journal of Heterocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135038077","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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