Efficient Ultrasound Enhance Novel Series of 2-((E)-2,3-Dihydro-2-(4-(phenylthio)phenyl)benzo[b][1,4]thiazepin-4-yl)phenol as an Antimicrobial Agent

Abstract

An efficient synthesis of 1,5-Benzothiazepines via Michael addition of corresponding (E)-1-(2-hydroxyphenyl)-3-(4-(phenylthio)phenyl)prop-2-en-1-one is described under ultrasound irradiation. A series of novel 2-((E)-2,3-dihydro-2-(4-(phenylthio)phenyl)benzo [b][1,4]thiazepin-4-yl)phenol derivatives was confirmed on the basis of 1 H NMR, Mass, IR spectral data and Elemental analysis. The synthesized compounds were evaluated for their antimicrobial activities. Most of the compounds were found to be comparable potent than the reference standard drugs. Utilization of ultrasound irradiation, simple reaction conditions, isolation, and purification makes this manipulation very interesting from an economic and environmental perspective.

Benzo[1,5]thiazepine: Synthesis, Reactions, Spectroscopy, and Applications

“…Scheme 4: Cyclocondensation reaction of (E)-N-(4-(3-(2-chloro-5,6,7,8-substituted-quinolin-3-yl)acryloyl)phenyl)-methylbenzenesulfonamide with 2-aminothiophenol in ethanol in presence of bi-catalyst. 3 COOH. 1-Phenyl-2-(2 -1,2,3-triazol-2-yl) ethanone 41 when heated under reflux with benzaldehyde and catalytic amount of piperidine gave 1,3-diphenyl-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one 42.…”

“…The latter triazole upon thermal reaction with o-aminothiophenol and CF 3 COOH for 5-6 h yielded 1,5-benzothiazepine containing 1,2,4-triazole moiety 43 (43 toutemeric form in solvent) in 72.7% yield [10] (Scheme 7). 3 COOH. 1-(2-Phenyl-2H-1,2,3-triazol-4-yl)-3-(p-substituted-phenyl)prop-2-en-1-ones 44a-d (prepared from the desired aromatic aldehydes and 1-(2-phenyl-2H-1,2,3-triazol-4-yl)ethanone) on reaction with o-aminothiophenol, in EtOH under reflux in the presence of CF 3 COOH gave 2,3-dihydro [1,5]benzothiazepines 45a-e in good yield (Scheme 8) [11] (Scheme 8).…”

“…1-(2-Phenyl-2H-1,2,3-triazol-4-yl)-3-(p-substituted-phenyl)prop-2-en-1-ones 44a-d (prepared from the desired aromatic aldehydes and 1-(2-phenyl-2H-1,2,3-triazol-4-yl)ethanone) on reaction with o-aminothiophenol, in EtOH under reflux in the presence of CF 3 COOH gave 2,3-dihydro [1,5]benzothiazepines 45a-e in good yield (Scheme 8) [11] (Scheme 8). 3 COOH. The , -unsaturated carbonyl compounds 48a-c were prepared by a condensation reaction of 4-acetyl-2-phenyl-1,2,3-triazole 46 with substituted aldehydes 47a-c.…”

“…In comparison, upon using conventional method, the yield of 70a was 57% after heating 4-5 h at 65 ∘ C. Similarly, the thiazepines 70b-g were synthesized in good yield from 69b-g and o-aminothiophenol in EtOH under ultrasonic irradiation method. A proposed Mechanism was outlined for the synthesis of the thiazepines via [1,4] and [1,2] addition of o-aminothiophenol to the chalcones 69 under ultrasonic irradiation [3] (Scheme 14).…”

“…Some of the 1,5-benzothiazepine derivatives were also used clinically for CNS disorders which includes thiazesim and quetiapine fumarate. Moreover, 1,5-benzothiazepine moiety is a privileged class of pharmacophore, as compounds bearing this structural unit possess a broad spectrum of biological activities such as anticonvulsant, Ca +2 channel antagonist, antianginal, anti HIV, squalene synthetase inhibitor, V 2 arginine vasopressin receptor antagonist, and HIV-1 reverse transcriptase inhibitor [1][2][3].…”