SYNTHESIS OF EPEREZOLID-LIKE MOLECULES AND EVALUATION OF THEIR ANTIMICROBIAL ACTIVITIES

Meltem Yolal*, Serap Basoglu*, Hakan Bektas**, Serpil Demirci*, Sengul Alpay-Karaoglu*** and Ahmet Demirbas*^#

^#Phone: +90 462 3772600; fax: +90 4623253196; e-mail: ndemirbas651@mynet.com

*Department of Chemistry, Faculty of Arts and Sciences, Karadeniz Technical University, Trabzon, Turkey
**Giresun University, Department of Chemistry, Giresun, Turkey
***Rize University, Department of Biology, Rize, Turkey

Abstract. 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 afforded the 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.

Keywords: piperazin, 1,3-thiazolidinone, 1,2,4-triazole, 1,3,4-thiadiazole, antimicrobial activity.

Биоорг.химия 2012, 38 (5):610-620