Synthesis of novel imidazo[1,2-a] pyridines and evaluation of their antifungal activities

Goktas F., Cesur N., Satana D., Uzun M.

TURKISH JOURNAL OF CHEMISTRY, cilt.38, sa.4, ss.581-591, 2014 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 38 Sayı: 4
  • Basım Tarihi: 2014
  • Doi Numarası: 10.3906/kim-1307-14
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.581-591
  • Anahtar Kelimeler: Imidazo[1,2-a] pyridine, hydrazinecarbothioamide, 4-oxo-1,3-thiazolidine, 1,3,4-oxadiazole, antifungal activity, ACYLTHIOSEMICARBAZIDES, 1,3,4-OXADIAZOLES, DERIVATIVES
  • İstanbul Üniversitesi Adresli: Evet

Özet

New 2-(imidazo[1,2-a] pyridin-2-ylcarbonyl)-N-substituted hydrazinecarbothioamides (4a-j), N'-(3-substituted-4-oxo-1,3-thiazolidin-2-ylidene) imidazo[1,2-a] pyridine-2-carbohydrazides (5a-f), and N-(nonsubstituted/4-substituted phenyl)-5-(imidazo[1,2-a] pyridine-2-yl)-1,3,4-oxadiazole-2-amines (6a-d) were synthesized from imidazo[1,2-a] pyridine-2-carbohydrazide (3) and evaluated for antifungal activity against Microsporum gypseum NCPF 580, M. canis, Trichophytontonsurans NCPF 245, T. rubrum, Candida albicans ATCC 10231, and C. parapsilosis ATCC 22019 using amphotericin B as the standard. The chemical structures of the compounds were confirmed by elemental analysis, IR, H-1 NMR, C-13 NMR, HMBC (C-13, H-1), and mass spectra. Most of the tested compounds showed moderate antifungal activity. Hydrazinecarbothioamide derivatives 4h and 4f exhibited the highest activity against M. canis (MIC: 2 mu g mL(-1) and 4 mu g mL(-1), respectively).