Synthesis and microbiological activity of some N-(2-hydroxy-4-substitutedphenyl)benzamides, phenylacetamides and furamides as the possible metabolites of antimicrobial active benzoxazoles.
The synthesis of some N-(2-hydroxy-4-substitutedphenyl)benzamides, phenylacetamides and furamides as the possible metabolites of benzoxazoles (II1-15) was performed in order to determine their in vitro antimicrobial activity against three Gram-positive bacteria, two Gram-negative bacteria and the fungus Candida albicans and their activities were compared with several control drugs. The compounds II11, II12, and II13 were found active at a MIC value of 12.5 microg/ml against the Gram-negative microorganism Pseudomonas aeruginosa. Most of the compounds show antibacterial activity at MIC a value of 25 microg/ml against the Gram-positive bacteria Staphylococcus aureus. For the antifungal activity against C. albicans, compound II10 was found more active than the other derivatives. The antimicrobial activity of some of these benzamides, phenylacetamides (II1 and II10) which are the possible metabolites of benzoxazoles, was also compared to their corresponding cyclic analogues III-IV. Compound II10 possesses two dilutions better antifungal activity than its cyclic analogue, benzoxazole IV, against C. albicans.
Aki-Sener
Esin
E
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ankara University, Tandogan, Turkey. sener@pharmacy.ankara.edu.tr
Bingöl
Kamuran K
KK
Temiz-Arpaci
Ozlem
O
Yalçin
Ismail
I
Altanlar
Nurten
N
D000081:Acetamides / Q000138:chemical synthesis* / Q000494:pharmacology*; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001549:Benzamides / Q000138:chemical synthesis* / Q000494:pharmacology*; D001583:Benzoxazoles / Q000737:chemistry; D002176:Candida albicans / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D005663:Furans / Q000138:chemical synthesis* / Q000494:pharmacology*; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D013055:Spectrophotometry, Infrared
D000081:Acetamides; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D001549:Benzamides; D001583:Benzoxazoles; D005663:Furans; C004932:diloxanide furoate