Novel Thioethers of Dihydroartemisinin Exhibiting Their Biological Activities

IF 1.1 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Heteroatom Chemistry Pub Date : 2023-02-09 DOI:10.1155/2023/6761186

Ngoc-Hung Truong, Thị Ngọc Lam Trần, K. Hoang, D. Ninh, Viet Duc Le, Duc Anh Le, V. Luu

引用次数: 1

Abstract

Eleven conjugates between dihydroartemisinin (DHA) with thiols containing both ether and thioether bonds were designed, synthesized by a two-step procedure including etherification and S-alkylation. Analysis of the NMR spectral data indicated that the dimer of DHA with thiols 6-mercaptopurine and 2-mercaptoimidazole was produced with yields of 31% and 62%, respectively. Furthermore, the tautomerization of thiol 5-methoxy-2-mercaptobenzimidazole led to the formation of a mixture of two isomers in which they might be interchangeable through a dynamic tautomeric equilibrium in the solution. Screening in vitro biological activities revealed that most of the synthesized conjugates showed good cytotoxic and anti-inflammatory activity, while three of them displayed α-glucosidase inhibitory activity. Notably, two conjugates 5d and 5e of DHA with thiols 2-mercaptopyrimidine and 2-mercaptobenzothiazole had an effect in all tested activities in which conjugate 5e is the most potent.

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新型双氢青蒿素硫醚类化合物的生物活性研究

设计了双氢青蒿素(DHA)与含有醚和硫醚键的硫醇之间的11个偶联物，通过醚化和s -烷基化两步合成。核磁共振光谱数据分析表明，DHA与巯基巯基嘌呤和巯基咪唑二聚体的产率分别为31%和62%。此外，巯基5-甲氧基-2-巯基苯并咪唑的互变异构化导致了两种异构体的混合物的形成，其中它们可能通过溶液中的动态互变异构平衡而可互换。体外生物活性筛选结果表明，大多数合成的缀合物具有良好的细胞毒和抗炎活性，其中3个具有α-葡萄糖苷酶抑制活性。值得注意的是，DHA与硫醇- 2-巯基嘧啶和2-巯基苯并噻唑的两个共轭物5d和5e在所有测试的活性中都有影响，其中共轭物5e最有效。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Heteroatom Chemistry 化学-化学综合

CiteScore

1.20

自引率

0.00%

发文量

审稿时长

6 months

期刊介绍： Heteroatom Chemistry brings together a broad, interdisciplinary group of chemists who work with compounds containing main-group elements of groups 13 through 17 of the Periodic Table, and certain other related elements. The fundamental reactivity under investigation should, in all cases, be concentrated about the heteroatoms. It does not matter whether the compounds being studied are acyclic or cyclic; saturated or unsaturated; monomeric, polymeric or solid state in nature; inorganic, organic, or naturally occurring, so long as the heteroatom is playing an essential role. Computational, experimental, and combined studies are equally welcome. Subject areas include (but are by no means limited to): -Reactivity about heteroatoms for accessing new products or synthetic pathways -Unusual valency main-group element compounds and their properties -Highly strained (e.g. bridged) main-group element compounds and their properties -Photochemical or thermal cleavage of heteroatom bonds and the resulting reactivity -Uncommon and structurally interesting heteroatom-containing species (including those containing multiple bonds and catenation) -Stereochemistry of compounds due to the presence of heteroatoms -Neighboring group effects of heteroatoms on the properties of compounds -Main-group element compounds as analogues of transition metal compounds -Variations and new results from established and named reactions (including Wittig, Kabachnik–Fields, Pudovik, Arbuzov, Hirao, and Mitsunobu) -Catalysis and green syntheses enabled by heteroatoms and their chemistry -Applications of compounds where the heteroatom plays a critical role. In addition to original research articles on heteroatom chemistry, the journal welcomes focused review articles that examine the state of the art, identify emerging trends, and suggest future directions for developing fields.