Synthesis, anti-microbial activity, and cytotoxicity of novel 1-[5-[6-[(2-benzoylbenzofuran-5-yl)methyl]-2-oxo-2H-chromen-3-yl]thiazol-2-yl]urea derivatives

doi:10.1007/s00706-016-1838-z

Paper

Synthesis, anti-microbial activity, and cytotoxicity of novel 1-[5-[6-[(2-benzoylbenzofuran-5-yl)methyl]-2-oxo-2H-chromen-3-yl]thiazol-2-yl]urea derivatives

Published Jun 1, 2017 · B. Shankar, P. Jalapathi, M. Nagamani

Monatshefte für Chemie - Chemical Monthly

UNKNOWN SJR score

14

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

A series of novel 1-[5-[6-[(2-benzoylbenzofuran-5-yl)methyl]-2-oxo-2H-chromen-3-yl]thiazol-2-yl]urea derivatives were synthesized by the reaction of 3-(2-aminothiazol-5-yl)-6-[(2-benzoylbenzofuran-5-yl)methyl]-2H-chromen-2-one with various substituted amines and triphosgene, in the presence of a base. The chemical structures of newly synthesized compounds were elucidated by 1H NMR, 13C NMR, IR, MS, and HRMS spectral data. The synthesized compounds evaluated for their inhibitory effects as anti-microbial activity and cytotoxicity. Most of the compounds exhibited a promising anti-microbial activity against the selected Gram-positive and Gram-negative bacterial strains at MIC values ranging from 0.071 to 0.199 μM and fungal pathogen was moderate to be good. The in vitro cytotoxicity testing of the title compounds was performed against cervical cancer (HeLa) cell lines. In the preliminary MTT cytotoxicity studies, the results have shown that there are a few of the synthesized compounds which exhibit a significant cytotoxicity at microliter concentration were found to non-toxic, their IC50 values ranging from 49.322/15 to 52.715/15 mm3.Graphical abstract

Study Snapshot

Novel 1-[5-[6-[(2-benzoylbenzofuran-5-yl)methyl]-2-oxo-2H-chromen-3-yl]thiazol-2-yl]urea derivatives show promising anti-microbial activity and low cytotoxicity against cervical cancer cell lines

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

Synthesis, anti-microbial activity, and cytotoxicity of novel 1-[5-[6-[(2-benzoylbenzofuran-5-yl)methyl]-2-oxo-2H-chromen-3-yl]thiazol-2-yl]urea derivatives

Sign up to use Study Snapshot

References

Synthesis, antioxidant and carbonic anhydrase I and II inhibitory activities of novel sulphonamide-substituted coumarylthiazole derivatives

Novel sulphonamide-substituted coumarylthiazole derivatives show inhibitory activity on carbonic anhydrase I and II, with the strongest inhibitor being N-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)

Synthesis of polybrominated benzimidazole and benzotriazole derivatives containing a tetrazole ring and their cytotoxic activity

Polybrominated benzimidazole and benzotriazole derivatives containing a tetrazole moiety exhibit significant cytotoxicity at micromolar concentrations against human T-cell lymphoblast and breast adenocarcinoma cell lines.

Synthesis, antioxidant and anticholinesterase activities of novel coumarylthiazole derivatives.

Novel coumarylthiazole derivatives show inhibitory activity against acetylcholinesterase and butyrylcholinesterase, with f8 showing the most potent anticholinesterase activity and e31 showing the strongest antioxidant activity.

Synthesis and pharmacological evaluation of some novel 2-(5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)-4-(coumarin-3-yl)thiazoles.

Novel 2-(5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)-4-(coumarin-3-yl)thiazoles show significant to moderate anti-inflammatory activity and good broad spectrum antibacterial activity against various bacteria.

Synthesis, antitumor and antioxidant evaluation of some new thiazole and thiophene derivatives incorporated coumarin moiety

3-Acetylcoumarin (1) is a key intermediate for the synthesis of various coumarin derivatives, which were evaluated as antitumor and antioxidant agents.

Synthesis and antimicrobial properties of some new thiazolyl coumarin derivatives.

New thiazolyl coumarin derivatives show promising antimicrobial activity against various bacteria, including Mycobacterium tuberculosis and Candida albicans.

An efficient non-ionic surfactant catalyzed multicomponent synthesis of novel benzylamino coumarin derivative via Mannich type reaction in aqueous media

This study developed an efficient non-ionic surfactant-catalyzed multicomponent synthesis of novel benzylamino coumarin derivatives from secondary amines, aromatic aldehyde, and 4-hydroxy coumarin in aqueous media.

[Targeted therapies in breast cancer].

Targeted therapies in breast cancer include trastuzumab, lapatinib, and new treatments targeting HER2, PI3K-AKT-mTOR, and antiangiogenic pathways.

Pharmacological significance of triazole scaffold

Triazole nucleus is a key structural component in various medicinal agents, with broad and potent pharmacological activities across various drug categories.

Citations

Synthesis of newer substituted chalcone linked 1,2,3-triazole analogs and evaluation of their cytotoxic activities

The synthesized chalcone 1,2,3-triazole analogs show moderate to good cytotoxic activities against A549 lung cancer cells, with compound 6j showing good selectivity.

Synthesis and potent antimicrobial activity of novel coumarylthiazole α-aminophosphonates derivatives

Novel coumarylthiazole -aminophosphonates derivatives show moderate antibacterial and antifungal activity against various pathogens, making them potential antimicrobial drug candidates.

Characterization and molecular docking studies of substituted 3-(2-benzylidenehydrazinyl)-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines synthesized via a one-pot, three-component reaction

Synthesized compounds 4f, 4 g, and 4k show promising binding interactions with p38MAPK, offering potential therapeutic applications.

A decade review of triphosgene and its applications in organic reactions.

Triphosgene has become a versatile reagent in organic synthesis, facilitating the preparation of value-added compounds and emerging applications in complex molecules, polymer synthesis, and flow chemistry.

Overview on developed synthesis procedures of coumarin heterocycles

Recent research on synthesis methods of coumarin heterocycles, including green conditions, shows promising potential for valuable biological and pharmaceutical properties.

Synthesis of novel 3-[(2R)-2-[(2S)-6-fluoro-3,4-dihydro-2H-chromen-2-yl]-2-hydroxyethyl]-urea/thiourea derivatives and evaluation of their antimicrobial activities

Novel 3-[(2R)-2-[(2S)-6-fluoro-3,4-dihydro-2H-chromen-2-yl]-2-hydroxyethyl]-urea/thiourea derivatives show moderate to excellent antimicrobial activity against both bacterial and

Synthesis, Antibacterial Activity, and Cytotoxicity of Newly Synthesized N-Substituted 5,6-Dimethoxy-1H-indole Derivatives

Novel N-substituted 5,6-dimethoxy-1H-indole derivatives show promising antibacterial activity and potential anticancer activity against MCF7 breast cancer cell line.

Synthesis, antimycobacterial activity, and acid dissociation constants of polyfunctionalized 3-[2-(pyrrolidin-1-yl)thiazole-5-carbonyl]-2H-chromen-2-one derivatives

Polyfunctionalized 3-[2-(pyrrolidin-1-yl)thiazole-5-carbonyl]-2H-chromen-2-one derivatives show antimycobacterial activity against M. tuberculosis H37Rv strain, with acid dissociation constants associated with SH, OH,

Synthesis, anti-microbial activity, and cytotoxicity of novel 1-[5-[6-[(2-benzoylbenzofuran-5-yl)methyl]-2-oxo-2H-chromen-3-yl]thiazol-2-yl]urea derivatives

Sign up to use Study Snapshot

References

Synthesis, antioxidant and carbonic anhydrase I and II inhibitory activities of novel sulphonamide-substituted coumarylthiazole derivatives

Novel sulphonamide-substituted coumarylthiazole derivatives show inhibitory activity on carbonic anhydrase I and II, with the strongest inhibitor being N-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)

Synthesis of polybrominated benzimidazole and benzotriazole derivatives containing a tetrazole ring and their cytotoxic activity

Polybrominated benzimidazole and benzotriazole derivatives containing a tetrazole moiety exhibit significant cytotoxicity at micromolar concentrations against human T-cell lymphoblast and breast adenocarcinoma cell lines.

Synthesis, antioxidant and anticholinesterase activities of novel coumarylthiazole derivatives.

Novel coumarylthiazole derivatives show inhibitory activity against acetylcholinesterase and butyrylcholinesterase, with f8 showing the most potent anticholinesterase activity and e31 showing the strongest antioxidant activity.

Synthesis and pharmacological evaluation of some novel 2-(5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)-4-(coumarin-3-yl)thiazoles.

Novel 2-(5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)-4-(coumarin-3-yl)thiazoles show significant to moderate anti-inflammatory activity and good broad spectrum antibacterial activity against various bacteria.

Synthesis, antitumor and antioxidant evaluation of some new thiazole and thiophene derivatives incorporated coumarin moiety

3-Acetylcoumarin (1) is a key intermediate for the synthesis of various coumarin derivatives, which were evaluated as antitumor and antioxidant agents.

Synthesis and antimicrobial properties of some new thiazolyl coumarin derivatives.

New thiazolyl coumarin derivatives show promising antimicrobial activity against various bacteria, including Mycobacterium tuberculosis and Candida albicans.

An efficient non-ionic surfactant catalyzed multicomponent synthesis of novel benzylamino coumarin derivative via Mannich type reaction in aqueous media

This study developed an efficient non-ionic surfactant-catalyzed multicomponent synthesis of novel benzylamino coumarin derivatives from secondary amines, aromatic aldehyde, and 4-hydroxy coumarin in aqueous media.

[Targeted therapies in breast cancer].

Targeted therapies in breast cancer include trastuzumab, lapatinib, and new treatments targeting HER2, PI3K-AKT-mTOR, and antiangiogenic pathways.

Pharmacological significance of triazole scaffold

Triazole nucleus is a key structural component in various medicinal agents, with broad and potent pharmacological activities across various drug categories.

Citations

Synthesis of newer substituted chalcone linked 1,2,3-triazole analogs and evaluation of their cytotoxic activities

The synthesized chalcone 1,2,3-triazole analogs show moderate to good cytotoxic activities against A549 lung cancer cells, with compound 6j showing good selectivity.

Synthesis and potent antimicrobial activity of novel coumarylthiazole α-aminophosphonates derivatives

Novel coumarylthiazole -aminophosphonates derivatives show moderate antibacterial and antifungal activity against various pathogens, making them potential antimicrobial drug candidates.

Characterization and molecular docking studies of substituted 3-(2-benzylidenehydrazinyl)-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines synthesized via a one-pot, three-component reaction

Synthesized compounds 4f, 4 g, and 4k show promising binding interactions with p38MAPK, offering potential therapeutic applications.

A decade review of triphosgene and its applications in organic reactions.

Triphosgene has become a versatile reagent in organic synthesis, facilitating the preparation of value-added compounds and emerging applications in complex molecules, polymer synthesis, and flow chemistry.

Overview on developed synthesis procedures of coumarin heterocycles

Recent research on synthesis methods of coumarin heterocycles, including green conditions, shows promising potential for valuable biological and pharmaceutical properties.

Synthesis of novel 3-[(2R*)-2-[(2S*)-6-fluoro-3,4-dihydro-2H-chromen-2-yl]-2-hydroxyethyl]-urea/thiourea derivatives and evaluation of their antimicrobial activities

Novel 3-[(2R*)-2-[(2S*)-6-fluoro-3,4-dihydro-2H-chromen-2-yl]-2-hydroxyethyl]-urea/thiourea derivatives show moderate to excellent antimicrobial activity against both bacterial and

Synthesis, Antibacterial Activity, and Cytotoxicity of Newly Synthesized N-Substituted 5,6-Dimethoxy-1H-indole Derivatives

Novel N-substituted 5,6-dimethoxy-1H-indole derivatives show promising antibacterial activity and potential anticancer activity against MCF7 breast cancer cell line.

Synthesis, antimycobacterial activity, and acid dissociation constants of polyfunctionalized 3-[2-(pyrrolidin-1-yl)thiazole-5-carbonyl]-2H-chromen-2-one derivatives

Polyfunctionalized 3-[2-(pyrrolidin-1-yl)thiazole-5-carbonyl]-2H-chromen-2-one derivatives show antimycobacterial activity against M. tuberculosis H37Rv strain, with acid dissociation constants associated with SH, OH,

Synthesis of novel 3-[(2R)-2-[(2S)-6-fluoro-3,4-dihydro-2H-chromen-2-yl]-2-hydroxyethyl]-urea/thiourea derivatives and evaluation of their antimicrobial activities

Novel 3-[(2R)-2-[(2S)-6-fluoro-3,4-dihydro-2H-chromen-2-yl]-2-hydroxyethyl]-urea/thiourea derivatives show moderate to excellent antimicrobial activity against both bacterial and