Synthesis, antimicrobial activity, and determination of the lipophilicity of ((cyclohex-3-enylmethylene)hydrazinyl)thiazole derivatives

被引：35

作者：

Biernasiuk, Anna ^{[1
]}

Kawczynska, Magdalena ^{[2
]}

Berecka-Rycerz, Anna ^{[3
]}

Rosada, Beata ^{[2
]}

Gumieniczek, Anna ^{[3
]}

Malm, Anna ^{[1
]}

Dzitko, Katarzyna ^{[4
]}

Laczkowski, Krzysztof Z. ^{[2
]}

机构：

[1] Med Univ Lublin, Fac Pharm, Lab Microbiol Diagnost, Dept Pharmaceut Microbiol, Chodzki 1, PL-20093 Lublin, Poland

[2] Nicolaus Copernicus Univ, Fac Pharm, Dept Chem Technol & Pharmaceut, Jurasza 2, PL-85089 Bydgoszcz, Poland

[3] Med Univ Lublin, Fac Pharm, Dept Med Chem, Jaczewskiego 4, PL-20090 Lublin, Poland

[4] Univ Lodz, Fac Biol & Environm Protect, Dept Immunoparasitol, Banacha 12-16, PL-90237 Lodz, Poland

来源：

MEDICINAL CHEMISTRY RESEARCH | 2019年 / 28卷 / 11期

关键词：

Thiazole; Antimicrobial activity; Candida spp; Lipophilicity; Thin-layer chromatography; MOLECULAR DOCKING; ANTICONVULSANTS DESIGN; DFT CALCULATION; ANTIFUNGAL; THIAZOLES; FLUCONAZOLE;

D O I：

10.1007/s00044-019-02433-2

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Synthesis and investigation of antimicrobial activity of fifteen novel thiazoles containing cyclohexene moiety are presented. Among the derivatives, compounds 3a-3d, 3f, 3n, and 3o showed very strong activity against the reference Candida spp. strains with MIC = 0.015-3.91 mu g/ml. The activity of these compounds is similar and even higher than the activity of nystatin used as positive control. Compounds 3d, 3f, 3n, 3o showed the highest activity with very strong effect towards most of yeasts isolated from clinical materials with MIC = 0.015-7.81 mu g/ml. The cytotoxicity studies for the most active compounds showed that Candida spp. growth was inhibited at noncytotoxic concentrations for the mammalian L929 fibroblast. In addition, a good correlation was obtained between lipophilicity of compounds determined using reversed phase thin-layer chromatography and their antifungal activity.

引用

页码：2023 / 2036

页数：14

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