新型5-（硝基噻吩-2-基）-1,3,4-噻二唑衍生物：针对硕大利什曼原虫前鞭毛体阶段的合成及抗利什曼活性
Novel 5-(nitrothiophene-2-yl)-1,3,4-Thiadiazole Derivatives: Synthesis and Antileishmanial Activity against promastigote stage of Leishmania major.
作者信息
Sadat-Ebrahimi Seyed Esmail, Mirmohammadi Maryam, Mojallal Tabatabaei Zahra, Azimzadeh Arani Marjan, Jafari-Ashtiani Sogol, Hashemian Mahsa, Foroumadi Parham, Yahya-Meymandi Azadeh, Moghimi Setareh, Moshafi Mohammad Hassan, Norouzi Peiman, Kabudanian Ardestani Susan, Foroumadi Alireza
机构信息
Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran.
Department of Biochemistry, Institute of Biochemistry and Biophysics, University of Tehran, Tehran, Iran.
出版信息
Iran J Pharm Res. 2019 Fall;18(4):1816-1822. doi: 10.22037/ijpr.2019.14547.12476.
In this study, a series of novel compounds based on 5-(5-nitrothiophene-2-yl)-1,3,4-thiadiazole possessing (het) aryl thio pendant at C-2 position of thiadiazole ring is developed and evaluated as antileishmanial agents using MTT colorimetric assay. 10 New compounds containing aryl and heteroaryl derivatives, started from thiophene-2-carbaldehyde in five steps, were synthesized in good to excellent yields and characterized by H-NMR, C-NMR, and IR spectroscopy. Through the compounds , methylimidazole containing derivative was recognized as the most active compound against promastigotes exhibiting IC values of 11.2µg/mL and 7.1µg/mL after 24 and 48 h, respectively. This compound is > 4 fold more effective than Glucantime as a standard drug (IC = 50 µg/mL after 24 h and 25 µg/mL after 48 h).
在本研究中，开发了一系列基于5-(5-硝基噻吩-2-基)-1,3,4-噻二唑的新型化合物，这些化合物在噻二唑环的C-2位具有（杂）芳基硫代侧链，并使用MTT比色法作为抗利什曼原虫剂进行了评估。从噻吩-2-甲醛开始，分五步合成了10种含芳基和杂芳基衍生物的新化合物，产率良好至优异，并通过H-NMR、C-NMR和红外光谱进行了表征。通过这些化合物，含甲基咪唑的衍生物被认为是对前鞭毛体最具活性的化合物，在24小时和48小时后分别表现出11.2µg/mL和7.1µg/mL的IC值。作为标准药物，该化合物的有效性比葡糖胺锑钠高4倍以上（24小时后IC = 50 µg/mL，48小时后IC = 25 µg/mL）。
Zotero 插件