Pub Date : 2023-09-30DOI: 10.59467/ijhc.2023.33.289
S. Subramanyam, Ramu Samineni, Sunil Kumar Kadiri, J. P. Yanadaiah, Phaneendranath Jonnalagedda, Krishna Veni Chikkula, Sampath A. Gouru
The anti-inflammatory, analgesic, and antiulcer activities of eight new hydrazide Schiff bases and eight new Mannich bases of indole derivatives were investigated. 2-Methyl-1H-indole-3-carboxylate (III) on hydrazinolysis gave 2-methyl-1H-indole-3-carbohydrazide (IV), which on reaction with aldehydes gave corresponding hydrazide Schiff bases Va–Vh. The reaction of IV with formaldehyde, different aliphatic, aromatic, and heterocyclic amines afforded the Mannich bases of indole derivatives (VIa–VIe). The results of biological studies revealed that Schiff bases with 2,4-dichlorobenzaldehyde (Vh) and 2-chlorobenzaldehyde (Vb) were potent anti-inflammatory, analgesic, and antiulcer activities. Mannich bases (VIh and VIc) having -NO2 and -Cl groups in the paralocation of the heterocyclic nucleus displayed effective anti-inflammatory, analgesic, and antiulcer activities.
{"title":"Synthesis and In-vivo Bioactivity Studies of Some New Hydrazide Schiff Bases and Mannich Bases of Indole Derivatives","authors":"S. Subramanyam, Ramu Samineni, Sunil Kumar Kadiri, J. P. Yanadaiah, Phaneendranath Jonnalagedda, Krishna Veni Chikkula, Sampath A. Gouru","doi":"10.59467/ijhc.2023.33.289","DOIUrl":"https://doi.org/10.59467/ijhc.2023.33.289","url":null,"abstract":"The anti-inflammatory, analgesic, and antiulcer activities of eight new hydrazide Schiff bases and eight new Mannich bases of indole derivatives were investigated. 2-Methyl-1H-indole-3-carboxylate (III) on hydrazinolysis gave 2-methyl-1H-indole-3-carbohydrazide (IV), which on reaction with aldehydes gave corresponding hydrazide Schiff bases Va–Vh. The reaction of IV with formaldehyde, different aliphatic, aromatic, and heterocyclic amines afforded the Mannich bases of indole derivatives (VIa–VIe). The results of biological studies revealed that Schiff bases with 2,4-dichlorobenzaldehyde (Vh) and 2-chlorobenzaldehyde (Vb) were potent anti-inflammatory, analgesic, and antiulcer activities. Mannich bases (VIh and VIc) having -NO2 and -Cl groups in the paralocation of the heterocyclic nucleus displayed effective anti-inflammatory, analgesic, and antiulcer activities.","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":"135038088","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.2023.33.285
Parth P. Patel, Navin B. Patel, Manesh S. Tople, Vatsal M. Patel, Dhanji P. Rajani
2-(Arylidene)-1-thia-4-azaspiro[4.5]decan-3-ones (3a-e, 4a-e) were synthesized from the 1-thia-4-azaspiro[4.5] decan-3-one through Knoevenagel reaction using the microwave method. In vitro, antibacterial and antitubercular screening of synthetic derivatives 3a-e and 4a-e revealed that compounds 3a and 4b are considerably potent as antibacterial agents against Escherichia coli with MIC = 50 μg/mL and MIC = 50 μg/mL, respectively. Compounds 3e and 4e possessed very good antitubercular activity with MIC = 0.47 μg/mL and MIC = 0.43 μg/mL. The results of molecular docking analysis supported the results of in vitro evaluation as against antibacterial protein compound 3a showed the lowest binding energy and against antitubercular protein, while 3e and 4e were highly attached?
{"title":"Microwave-Assisted Synthesis of 2-(Arylidene)-1-thia-4-azaspiro[4.5]decan-3-ones and their Antibacterial, Antitubercular, and In Silico Screening","authors":"Parth P. Patel, Navin B. Patel, Manesh S. Tople, Vatsal M. Patel, Dhanji P. Rajani","doi":"10.59467/ijhc.2023.33.285","DOIUrl":"https://doi.org/10.59467/ijhc.2023.33.285","url":null,"abstract":"2-(Arylidene)-1-thia-4-azaspiro[4.5]decan-3-ones (3a-e, 4a-e) were synthesized from the 1-thia-4-azaspiro[4.5] decan-3-one through Knoevenagel reaction using the microwave method. In vitro, antibacterial and antitubercular screening of synthetic derivatives 3a-e and 4a-e revealed that compounds 3a and 4b are considerably potent as antibacterial agents against Escherichia coli with MIC = 50 μg/mL and MIC = 50 μg/mL, respectively. Compounds 3e and 4e possessed very good antitubercular activity with MIC = 0.47 μg/mL and MIC = 0.43 μg/mL. The results of molecular docking analysis supported the results of in vitro evaluation as against antibacterial protein compound 3a showed the lowest binding energy and against antitubercular protein, while 3e and 4e were highly attached?","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":"135038090","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.2023.33.277
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.2023.33.277","DOIUrl":"https://doi.org/10.59467/ijhc.2023.33.277","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":"135038109","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.2023.33.355
Nisha Sharma, Rashmi Pundeer, Om Prakash
Dehydroacetic acid, commonly abbreviated as DHA, and its derivatives have been extensively used as important intermediates in organic synthesis particularly for the synthesis of heterocyclic compounds. The reaction of 8-aryloct-7-en-2,4,6-triones (DHA-triones, readily prepared from commercially available DHA by the use of a multistep procedure) with thiosemicarbazide led the formation of some new 2-methyl-5-styryl-7-thioxo-6,7-dihydropyrazolo[1,5-c] pyrimidines.
{"title":"8-Aryloct-7-en-2,4,6-triones as Useful Precursors for the Regioselective Synthesis of Some New 2-Methyl-5-styryl-7-thioxo-6,7-dihydropyrazolo[1,5-c]pyrimidines","authors":"Nisha Sharma, Rashmi Pundeer, Om Prakash","doi":"10.59467/ijhc.2023.33.355","DOIUrl":"https://doi.org/10.59467/ijhc.2023.33.355","url":null,"abstract":"Dehydroacetic acid, commonly abbreviated as DHA, and its derivatives have been extensively used as important intermediates in organic synthesis particularly for the synthesis of heterocyclic compounds. The reaction of 8-aryloct-7-en-2,4,6-triones (DHA-triones, readily prepared from commercially available DHA by the use of a multistep procedure) with thiosemicarbazide led the formation of some new 2-methyl-5-styryl-7-thioxo-6,7-dihydropyrazolo[1,5-c] pyrimidines.","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":"135038111","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}
Some new thiosemicarbazide derivatives (5*a-5*b and 6a-6f) were synthesized by multiple steps approaches starting from substituted anilines. The synthesized compounds were evaluated for their muscle relaxant activity by an in silico docking study against nicotinic muscarinic receptor (protein database [PDB] ID: 2XNU) using AutoDock Vina and Biovia discovery studio tools. The rotarod test was also used to evaluate the muscle-relaxing activity of the compounds. The results were compared with generic diazepam to corroborate both research findings. In the in silico test, all the compounds showed 2–4 interactions with the target nicotinic muscarinic receptor (PDB ID- 2XNU) having binding affinities in the range of −5.8–−7.8 Kcal/mol. Among them, the 6a compound demonstrated the most remarkable relaxant activity with four hydrogen bond interactions with amino acids TYRC: 52, ILE C: 88, ALA C:90, and GLN C:119 of the target molecule. In addition, the rotarod test showed that compounds 5*a and 6d also had more muscle-relaxing effects than diazepam.
{"title":"New Thiosemicarbazide Analogs as Antagonist of Nicotinic Muscarinic Receptors: Synthesis, In silico, and In vivo Screening","authors":"Varsha Jindaniya, Rakhi Mishra, Rupa Mazumder, Avijit Mazumder, Bhupinder Kapoor, Fahad Khan","doi":"10.59467/ijhc.2023.33.321","DOIUrl":"https://doi.org/10.59467/ijhc.2023.33.321","url":null,"abstract":"Some new thiosemicarbazide derivatives (5*a-5*b and 6a-6f) were synthesized by multiple steps approaches starting from substituted anilines. The synthesized compounds were evaluated for their muscle relaxant activity by an in silico docking study against nicotinic muscarinic receptor (protein database [PDB] ID: 2XNU) using AutoDock Vina and Biovia discovery studio tools. The rotarod test was also used to evaluate the muscle-relaxing activity of the compounds. The results were compared with generic diazepam to corroborate both research findings. In the in silico test, all the compounds showed 2–4 interactions with the target nicotinic muscarinic receptor (PDB ID- 2XNU) having binding affinities in the range of −5.8–−7.8 Kcal/mol. Among them, the 6a compound demonstrated the most remarkable relaxant activity with four hydrogen bond interactions with amino acids TYRC: 52, ILE C: 88, ALA C:90, and GLN C:119 of the target molecule. In addition, the rotarod test showed that compounds 5*a and 6d also had more muscle-relaxing effects than diazepam.","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":"135038274","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 : 2023-06-01DOI: 10.59467/ijhc.2023.33.221
M. Almehmadi, Ahad Amer Alsaiari, M. Allahyani, A. Aljuaid, S. Saha, M. Asif
{"title":"Synthesis and In Vitro Antimycobacterial Activity of Some New N-(5-Substituted Phenylthiazol-2-yl) Pyrimidine-5-Carboxamides","authors":"M. Almehmadi, Ahad Amer Alsaiari, M. Allahyani, A. Aljuaid, S. Saha, M. Asif","doi":"10.59467/ijhc.2023.33.221","DOIUrl":"https://doi.org/10.59467/ijhc.2023.33.221","url":null,"abstract":"","PeriodicalId":54993,"journal":{"name":"Indian Journal of Heterocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.3,"publicationDate":"2023-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42871184","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 : 2023-06-01DOI: 10.59467/ijhc.2023.33.183
Nidhi Negi, G. Chand, R. Gahtori, Santosh K. Upadhyay, Penny Joshi
{"title":"Synthesis, Antioxidant, and Antibacterial Potential of New Curcumin-Coumarin Hybrids","authors":"Nidhi Negi, G. Chand, R. Gahtori, Santosh K. Upadhyay, Penny Joshi","doi":"10.59467/ijhc.2023.33.183","DOIUrl":"https://doi.org/10.59467/ijhc.2023.33.183","url":null,"abstract":"","PeriodicalId":54993,"journal":{"name":"Indian Journal of Heterocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.3,"publicationDate":"2023-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47803563","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 : 2023-06-01DOI: 10.59467/ijhc.2023.33.191
K. Prabakaran, A. Nepolraj, Javid A. Malik, Vasyl I. Shupeniuk
{"title":"Synthesis, Characterization, Molecular Docking, and Biological Evaluation of 2-Methyl Perlolidine","authors":"K. Prabakaran, A. Nepolraj, Javid A. Malik, Vasyl I. Shupeniuk","doi":"10.59467/ijhc.2023.33.191","DOIUrl":"https://doi.org/10.59467/ijhc.2023.33.191","url":null,"abstract":"","PeriodicalId":54993,"journal":{"name":"Indian Journal of Heterocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.3,"publicationDate":"2023-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41553255","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 : 2023-06-01DOI: 10.59467/ijhc.2023.33.199
Sameh R. Elgogary, Emad M. El Telbani
{"title":"Design, Synthesis, and Anticancer Evaluation of New Coumarin and Pyrazole Derivatives Bearing Benzenesulfonamide Moiety","authors":"Sameh R. Elgogary, Emad M. El Telbani","doi":"10.59467/ijhc.2023.33.199","DOIUrl":"https://doi.org/10.59467/ijhc.2023.33.199","url":null,"abstract":"","PeriodicalId":54993,"journal":{"name":"Indian Journal of Heterocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.3,"publicationDate":"2023-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42162962","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 : 2023-06-01DOI: 10.59467/ijhc.2023.33.173
M. Almehmadi, Ahad Amer Alsaiari, M. Allahyani, A. Aljuaid, Abdulaziz Alsharif, M. Asif
{"title":"Synthesis and Antimicrobial Evaluation of 6-Aryl-3-(pyridin-4-yl)-[1,2,4]triazolo[3,4-b] [1,3,4]thiadiazoles","authors":"M. Almehmadi, Ahad Amer Alsaiari, M. Allahyani, A. Aljuaid, Abdulaziz Alsharif, M. Asif","doi":"10.59467/ijhc.2023.33.173","DOIUrl":"https://doi.org/10.59467/ijhc.2023.33.173","url":null,"abstract":"","PeriodicalId":54993,"journal":{"name":"Indian Journal of Heterocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.3,"publicationDate":"2023-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47444825","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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