Synthesis and microbiological activity of some substituted N-(2-hydroxy-4-nitrophenyl) benzamides and phenylacetamides as possible metabolites of antimicrobial active benzoxazoles

Oren İ., Aki-Sener E., Ertas C., Arpaci O., Yalcin I., Altanlar N.

TURKISH JOURNAL OF CHEMISTRY, cilt.28, sa.4, ss.441-449, 2004 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 28 Sayı: 4
  • Basım Tarihi: 2004
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.441-449
  • Anahtar Kelimeler: antimicrobial activity, benzamide, benzoxazole, phenylacetainide, BENZIMIDAZOLES, DERIVATIVES, AGENTS, OXAZOLO(4,5-B)PYRIDINES, BENZOTHIAZOLES, MITOCHONDRIA, ANTIFUNGAL, RESISTANCE
  • Ankara Üniversitesi Adresli: Evet

Özet

Some new antimicrobial active N-(2-hydroxy-4-nitrophenyl)-p-stibstituted benzamide and phenylacetamide analogues (I-II) were prepared by 2-step procedures from the corresponding carboxylic acids as possible metabolites of benzoxazoles. Their antimicrobial activities were tested against 3 Gram-positive and 2 Gram-negative bacteria with the fungus Candida albicans and were also compared with several control drugs. The compounds Ia, Id, IIa, and IIe were active at a MIC value of 12.5 mug/mL against the Gram-positive microorganism Bacillus subtilis. Most of the compounds exhibited antifungal activity at a MIC value of 12.5 mug/mL against C. albicans. On the other hand, the antimicrobial activity of some amide derivatives (Ia, Id, IIa-c) was also compared with their cyclic analogues, benzoxazole derivatives (III-IV). The compound Id significantly possessed 2 or 3 dilutions better antimicrobial activity than its heterocyclic derivative, 2-(p-t-butylphenyl)-5-nitrobenzoxazole, IIId, against Staphylococcus aureus, Streptococcus faecalis, Klebsiella pneumonia, and Escherichia coli.