Divergent Synthesis of Novel 3(5)-Aminoazole-Benzopyrone Hybrids and their Evaluation as α-Glucosidase Inhibitors.

IF 3.6 4区医学 Q2 CHEMISTRY, MEDICINAL

ChemMedChem Pub Date : 2024-11-19 DOI:10.1002/cmdc.202400525

Andrii S Myshko, Galyna P Mrug, Svitlana P Bondarenko, Bohdan A Demydchuk, Oleksandr L Kobzar, Vladyslav M Buldenko, Andriy I Vovk, Mykhaylo Frasinyuk

引用次数: 0

Abstract

An efficient approach has been developed for the trapping in situ generated benzopyrone-based ortho-quinone methide intermediates by 3- and 5-amino pyrazoles or isoxazoles. In cases of naturally occurring phenolic Mannich bases, hybrid compounds between the azole and flavonoid, namely, coumarin, chromone, isoflavone, and aurone were synthesized in moderate to good yields. It is remarkable that depending on 3- or 5-position of the amino group, the reaction led to the formation of C-4 or 3-NH substituted azole derivatives, respectively. In vitro studies showed that some of the obtained compounds bearing 5-aminoisoxazole part exhibit inhibitory activity towards α-glucosidase with IC50 values in the micromolar range.

查看原文本刊更多论文

新型 3(5)-Aminoazole-Benzopyrone Hybrids 的不同合成及其作为 α-葡萄糖苷酶抑制剂的评估。

我们开发了一种有效的方法，通过 3-和 5-氨基吡唑或异噁唑捕获原位生成的苯并吡喃酮基邻位醌甲酰胺中间体。在天然酚类曼尼希碱的情况下，唑类和黄酮类之间的杂交化合物，即香豆素、色酮、异黄酮和呋喃酮以中等至良好的产率合成。值得注意的是，根据氨基的 3 位或 5 位，反应分别会生成 C-4 或 3-NH 取代的唑衍生物。体外研究表明，所获得的一些含有 5-aminoisoxazole 部分的化合物对 α-葡萄糖苷酶具有抑制活性，其 IC50 值在微摩尔范围内。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

ChemMedChem 医学-药学

CiteScore

6.70

自引率

2.90%

发文量

280

审稿时长

1 months

期刊介绍： Quality research. Outstanding publications. With an impact factor of 3.124 (2019), ChemMedChem is a top journal for research at the interface of chemistry, biology and medicine. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. ChemMedChem publishes primary as well as critical secondary and tertiary information from authors across and for the world. Its mission is to integrate the wide and flourishing field of medicinal and pharmaceutical sciences, ranging from drug design and discovery to drug development and delivery, from molecular modeling to combinatorial chemistry, from target validation to lead generation and ADMET studies. ChemMedChem typically covers topics on small molecules, therapeutic macromolecules, peptides, peptidomimetics, and aptamers, protein-drug conjugates, nucleic acid therapies, and beginning 2017, nanomedicine, particularly 1) targeted nanodelivery, 2) theranostic nanoparticles, and 3) nanodrugs. Contents ChemMedChem publishes an attractive mixture of: Full Papers and Communications Reviews and Minireviews Patent Reviews Highlights and Concepts Book and Multimedia Reviews.