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Synthesis and antifungal activity of novel oxazolidin-2-one-linked 1,2,3-triazole derivatives†
RSC Medicinal Chemistry ( IF 4.1 ) Pub Date : 2017-10-17 00:00:00 , DOI: 10.1039/c7md00442g
Alejandra Ramírez-Villalva 1 , Davir González-Calderón 1 , Roxana I Rojas-García 1 , Carlos González-Romero 1 , Joaquín Tamaríz-Mascarúa 2 , Macario Morales-Rodríguez 3 , Nieves Zavala-Segovia 4 , Aydeé Fuentes-Benítes 1
Affiliation  

Novel oxazolidin-2-one-linked 1,2,3-triazole derivatives (4a–k) were synthesized by straightforward and versatile azide–enolate (3 + 2) cycloaddition. The series of compounds was screened for antifungal activity against four filamentous fungi as well as six yeast species of Candida spp. According to their efficiency and breadth of scope, they can be ordered as 4k > 4d > 4h > 4a, especially in relation to the activity displayed against Candida glabrata ATCC-34138, Trichosporon cutaneum ATCC-28592 and Mucor hiemalis ATCC-8690, i.e. compounds 4d, 4h and 4k showed excellent activity against C. glabrata (MIC 0.12, 0.25 and 0.12 μg mL−1, respectively), better than that of itraconazole (MIC 1 μg ml−1). The activity of compound 4d (MIC = 2 μg mL−1) was higher than that observed for the standard antifungal drug (MIC = 8 μg mL−1) against Trichosporon cutaneum, while compound 4k displayed an excellent antimycotic activity against Mucor hiemalis (MIC = 2 μg mL−1vs. 4 μg mL−1 for itraconazole). In addition, we describe herein a novel mild and eco-friendly synthetic protocol for obtaining β-ketosulfones (adducts to afford compounds 4a–k) from α-brominated carbonyls in an aqueous nanomicellar medium at room temperature.

中文翻译:

新型恶唑烷-2-单联1,2,3-三唑衍生物的合成和抗真菌活性†

通过简单且通用的叠氮-烯醇化物 (3 + 2) 环加成反应合成了新型恶唑烷-2-单连接 1,2,3-三唑衍生物 ( 4a–k )。筛选了该系列化合物对四种丝状真菌以及六种念珠菌属酵母的抗真菌活性。根据其效率和范围广度,它们可以排序为4k > 4d > 4h > 4a,特别是针对光滑念珠菌ATCC-34138、皮肤毛孢子ATCC-28592 和毛霉ATCC-8690 所表现出的活性,化合物4d4h4k光滑念珠菌表现出优异的活性(MIC分别为0.12、0.25和0.12 μg ml -1),优于伊曲康唑(MIC 1 μg ml -1)。化合物4d对皮肤毛孢子菌的活性(MIC = 2 μg mL -1)高于标准抗真菌药物(MIC = 8 μg mL -1),而化合物4k对冬毛霉表现出优异的抗真菌活性(MIC = 8 μg mL -1 )。 = 2 μg mL -1对比伊曲康唑4 μg mL -1)。此外,我们在此描述了一种新颖的温和且环保的合成方案,用于在室温下在水性纳米胶束介质中从 α-溴化羰基获得 β-酮砜(加合物以提供化合物4a-k )。
更新日期:2017-10-17
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