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

BASOGLU S., YOLAL M., DEMİRBAŞ A., Bektas H., Abbasoglu R., DEMİRBAŞ N.

TURKISH JOURNAL OF CHEMISTRY, vol.36, no.1, pp.37-53, 2012 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 36 Issue: 1
  • Publication Date: 2012
  • Doi Number: 10.3906/kim-1105-54
  • Journal Name: TURKISH JOURNAL OF CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.37-53
  • Karadeniz Technical University Affiliated: Yes

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, H-1-NMR, C-13-NMR and LC-MS) data. The antimicrobial activity study revealed that all compounds showed good antitubercular activities.

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, H-1-NMR, C-13-NMR and LC-MS) data. The antimicrobial activity study revealed that all compounds showed good antitubercular activities.