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6-三唑并-6-脱氧丁香酚糖苷的合成及其抗菌活性

Synthesis and antimicrobial activity of 6-triazolo-6-deoxy eugenol glucosides.

作者信息

de Souza Thiago Belarmino, Raimundo Paulo Otávio Botelho, Andrade Saulo Fernandes, Hipólito Taciane Maira Magalhães, Silva Naiara Chaves, Dias Amanda Latercia Tranches, Ikegaki Masaharu, Rocha Raissa Prado, Coelho Luiz Felipe Leomil, Veloso Marcia Paranho, Carvalho Diogo Teixeira, Dias Danielle Ferreira

机构信息

Instituto de Química, Universidade Federal de Alfenas, 37130-000, MG, Brazil.

Centro Universitário de Lavras, 37200-000, MG, Brazil.

出版信息

Carbohydr Res. 2015 Jun 17;410:1-8. doi: 10.1016/j.carres.2015.04.002. Epub 2015 Apr 13.

Abstract

A new series of 1,2,3-triazole eugenol glucosides were synthesized. The new compound structures were confirmed by MS, (1)H NMR and (13)C NMR. All of the synthesized compounds were screened for antimicrobial and cytotoxic activity. Five compounds exerted significant activity against the Gram-negative bacteria Salmonella typhimurium with low IC50 values (49.73-68.53 μΜ), and seven compounds were active against the Gram-positive bacteria Micrococcus luteus (42.89-210.94 μM). In vitro cytotoxicity on mouse spleen cells was also evaluated. One compound bearing a phenyl substituent at the triazole ring showed good activity against Salmonella typhimurium (49.73 μM) and low toxicity to normal cells (CC50=157.83 μM). Thus, the compounds herein can be considered for further modification for improving their antibacterial activity or obtaining novel antibacterial drug candidates.

摘要

合成了一系列新的1,2,3-三唑丁香酚糖苷。通过质谱、核磁共振氢谱(¹H NMR)和核磁共振碳谱(¹³C NMR)确定了新化合物的结构。对所有合成化合物进行了抗菌和细胞毒性活性筛选。五种化合物对革兰氏阴性菌鼠伤寒沙门氏菌具有显著活性,IC50值较低(49.73 - 68.53 μΜ),七种化合物对革兰氏阳性菌藤黄微球菌有活性(42.89 - 210.94 μM)。还评估了对小鼠脾细胞的体外细胞毒性。一种在三唑环上带有苯基取代基的化合物对鼠伤寒沙门氏菌显示出良好活性(49.73 μM),对正常细胞毒性较低(CC50 = 157.83 μM)。因此,本文中的化合物可考虑进一步修饰以提高其抗菌活性或获得新型抗菌候选药物。

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