Synthesis of linezolid-like molecules and evaluation of their antimicrobial activities

Authors: SERAP BAŞOĞLU, MELTEM YOLAL, AHMET DEMİRBAŞ, HAKAN BEKTAŞ, RZA ABBASOĞLU, NESLİHAN DEMİRBAŞ

Abstract: 3-Fluoro-4-(morpholin-4-yl)aniline (2), prepared from 3,4-difluoronitrobenzene, was converted to the corresponding Schiff base (3) by treatment with indol-3-carbaldehyde. The treatment of thiourea 4 and carbothioamide derivatives 9 with ethyl bromoacetate or 4-substituted phenacyl bromides generated the corresponding thiazolidinone (5 and 13) and thiazoline (6 and 12) derivatives, respectively. The acidic or basic treatment of carbothioamide 9 produced 1,3,4-thiadiazole (11) or 1,2,4-triazole (10) compounds, respectively. The structural assignments of the new compounds were based on elemental analysis and spectral (IR, ^1H-NMR, ^{13}C-NMR, and LC-MS) data. The antimicrobial activity study revealed that all compounds showed good antitubercular activities.

Keywords: 1,3-Thiazole, 1,3,4-thiadiazole, 1,2,4-triazole, linezolid, antimicrobial activity

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