Tekiner-Gulbas Betul, Temiz-Arpaci Ozlem, Yildiz Ilkay, Altanlar Nurten
Ankara University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, TR-06100 Tandogan, Ankara, Turkey.
Eur J Med Chem. 2007 Oct;42(10):1293-9. doi: 10.1016/j.ejmech.2007.01.022. Epub 2007 Jan 27.
Some new 2-(benzyl/p-chlorobenzyl)-5-[(substituted-thienyl/phenyl/phenylthiomethyl/benzyl)carbonylamino]benzoxazole derivatives have been synthesized by reacting 5-amino-2-(benzyl/p-chlorobenzyl)benzoxazoles with appropriate carboxylic acid chlorides. The structures of the synthesized compounds were confirmed by IR, (1)H NMR and MASS spectral data. In vitro antimicrobial activities of the compounds were investigated using twofold serial dilution technique against different two Gram-positive, two Gram-negative bacteria and three Candida spp. in comparison with standard drugs. Microbiological results indicated that the newly synthesized 2-(benzyl/p-chlorobenzyl)-5-[(substituted-thienyl/phenyl/phenylthiomethyl/benzyl)carbonylamino]benzoxazole derivatives (3-12) possessed a broad spectrum of activity having MIC values of 6.25-100 microg/ml against the tested microorganisms. Especially, with an MIC value of 6.25 microg/ml, 2-(p-chlorophenyl)-5-[(2,5-dimethylphenyl)carbonylamino]benzoxazole 4 displayed the same activity against Candida albicans as the standard drug clotrimazole.
通过使5-氨基-2-(苄基/对氯苄基)苯并恶唑与适当的酰氯反应，合成了一些新的2-(苄基/对氯苄基)-5-[(取代噻吩基/苯基/苯硫基甲基/苄基)羰基氨基]苯并恶唑衍生物。通过红外光谱、核磁共振氢谱和质谱数据对合成化合物的结构进行了确证。采用两倍系列稀释技术，与标准药物相比，研究了这些化合物对两种革兰氏阳性菌、两种革兰氏阴性菌和三种念珠菌属的体外抗菌活性。微生物学结果表明，新合成的2-(苄基/对氯苄基)-5-[(取代噻吩基/苯基/苯硫基甲基/苄基)羰基氨基]苯并恶唑衍生物(3-12)对受试微生物具有广谱活性，其最低抑菌浓度值为6.25-100微克/毫升。特别是，2-(对氯苯基)-5-[(2,5-二甲基苯基)羰基氨基]苯并恶唑4对白色念珠菌的活性与标准药物克霉唑相同，其最低抑菌浓度值为6.25微克/毫升。
