Design, synthesis and antimicrobial activities of some azole derivatives.

Three new 1,3,4-oxadiazole, 1,3-thiazolidine and 1,2,4-triazole derivatives were obtained starting from furan-2-carbohydrazide. Then, 1,2,4-triazole compound was converted to the corresponding Mannich bases using several secondary amines including piperidine, piperazine, morpholine or thiomorpholine moiety. The synthesis of 5-(furan-2-yl)-4-{[(4-methoxyphenyl)methylidene]amino}-4H-1,2,4-triazole-3-thiol (XIII) was performed starting from furan-2-carbohydrazide by three steps. The structures of the synthesized compounds were well characterized by elemental analyses, IR, 1H NMR, 13C NMR and mass spectral studies. Newly synthesized compounds were screened for their antimicrobial activities and some of them displayed activity against the tested microorganisms.

Synthesis of eperezolid-like molecules and evaluation of their antimicrobial activities.

3-Fluoro-4-(4-phenylpiperazin-1-yl)aniline (II) prepared from 3,4-difluoro nitrobenzene was converted to the corresponding Schiff bases (III) and (IV) by treatment with 4-methoxybenzaldehyde and indol-3-carbaldehyde, respectively. Treatment of amine (II) with 4-fluorophenyl isothiocyanate affordedthe corresponding thiourea derivative (V). Compound (V) was converted to thiazolidinone and thiazoline derivatives (VI) and (VII) by cyclocondensation with ethylbromoacetate or 4-chlorophenacylbromide, respectively. The synthesis of carbothioamide derivative (X) was performed starting from compound (II) by three steps. Treatment of compound (X) with sodium hydroxide, sulfuric acid, or chlorophenacyl bromide generated the corresponding 1,2,4-triazole (XI), 1,3,4-thiadiazole (XII), and 1,3-thiazolidinone (XIII) derivatives, respectively. The structural assignments of new compounds were based on their elemental analysis and spectral (IR, 1H-NMR, 13C-NMR, and LC-MS) data. In the antimicrobial activity study all the compounds revealed high anti-Mycobacterium smegmatis activity.