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

Yolal M., Basoglu S., BEKTAŞ H., Demirci S., ALPAY KARAOĞLU Ş., DEMİRBAŞ A.

RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, vol.38, no.5, pp.539-549, 2012 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 38 Issue: 5
  • Publication Date: 2012
  • Doi Number: 10.1134/s106816201205010x
  • Journal Name: RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.539-549
  • Keywords: piperazin, 1,3-thiazolidinone, 1,2,4-triazole, 1,3,4-thiadiazole, antimicrobial activity, ANTIBACTERIAL ACTIVITY, BIOLOGICAL EVALUATION, N-ALKYL, DERIVATIVES, OXAZOLIDINONE, PIPERAZINE, SCHIFF, ACID, 4-THIAZOLIDINONES, HYDRAZONES
  • Recep Tayyip Erdoğan University Affiliated: Yes

Abstract

3-Fluoro-4-(4-phenylpiperazin-l-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, H-1-NMR, C-13-NMR, and LC-MS) data. In the antimicrobial activity study all the compounds revealed high anti-Mycobacterium smegmatis activity.