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An Expedient Method for the Synthesis of 1,2,4‐Triazolo‐fused 1,5‐Benzodiazepine, 1,5‐Benzoxazepine, and 1,5‐Benzothiazepine Scaffolds: A Novel Seven‐membered Ring System of Biological Interest
Author(s) -
Sharma Aruna,
Kishore Dharma,
Singh Bhawani
Publication year - 2018
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3060
Subject(s) - chemistry , ring (chemistry) , enterobacter cloacae , antibacterial activity , fusarium oxysporum , proton nmr , candida albicans , stereochemistry , escherichia coli , organic chemistry , bacteria , enterobacteriaceae , microbiology and biotechnology , biochemistry , genetics , botany , biology , gene
New heterocyclic compounds 1‐(3‐methyl‐9 H ‐dibenzo[ b , f ][1,2,4]triazolo[4,3‐ d ][1,4]diazepin‐6‐yl)ethanone 8a , 1‐(3‐methyldibenzo[ b , f ][1,2,4]triazolo[4,3‐ d ][1,4]oxazepin‐6‐yl)ethanone 8b , and 1‐(3‐methyldibenzo[ b , f ][1,2,4]triazolo[4,3‐ d ][1,4]thiazepin‐6‐yl)ethanone 8c are synthesized from benzodiazepinone, benzoxazepinone, and benzothiazepinone derivatives. These heterocyclic scaffolds have wide medicinal importance. Best results were obtained in antibacterial screening against Escherichia coli , Enterobacter cloacae , and Staphylococcus aureus and antifungal screening against Candida albicans and Fusarium oxysporum . 1,1‐Diphenyl‐2‐picrylhydrazyl radical scavenging activities of compounds 6c , 7c , and 8c were tested in doses 10, 20, 30, 40, and 50 μg/mL and were expressed as IC 50 values and percent of inhibition with means ± standard deviation of three different concentrations of synthesized compounds. The assignment of the structures of synthesized compounds was made by thin‐layer chromatography, elemental analysis, IR, 1 H‐NMR, 13 C‐NMR, and liquid chromatography–mass spectrometry.