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

Bioorg Khim. 2012 Sep-Oct;38(5):610-20. doi: 10.1134/s106816201205010x.

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 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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetamides* / chemical synthesis
  • Acetamides* / chemistry
  • Acetamides* / pharmacology
  • Anti-Bacterial Agents* / chemical synthesis
  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / pharmacology
  • Antifungal Agents* / chemical synthesis
  • Antifungal Agents* / chemistry
  • Antifungal Agents* / pharmacology
  • Bacteria / growth & development*
  • Fungi / growth & development*
  • Molecular Structure
  • Oxazolidinones* / chemical synthesis
  • Oxazolidinones* / chemistry
  • Oxazolidinones* / pharmacology
  • Species Specificity

Substances

  • Acetamides
  • Anti-Bacterial Agents
  • Antifungal Agents
  • Oxazolidinones
  • eperezolid