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新型二肽磺酰胺类化合物的合成及其对碳酸酐酶 I、II、IX 和 XII 的抑制作用。

Synthesis of novel dipeptide sulfonamide conjugates with effective carbonic anhydrase I, II, IX, and XII inhibitory properties.

机构信息

Department of Chemistry, Faculty of Arts and Sciences, İnönü University, 44280 Malatya, Turkey.

Department of Basic Pharmaceutical Sciences, Faculty of Pharmacy, İnönü University, 44280 Malatya, Turkey.

出版信息

Bioorg Chem. 2018 Dec;81:311-318. doi: 10.1016/j.bioorg.2018.08.032. Epub 2018 Aug 27.

DOI:10.1016/j.bioorg.2018.08.032
PMID:30176570
Abstract

Twenty-four novel sulfonamide derivatives incorporating dipeptide tails were synthesized by facile acylation reactions of homosulfanilamide through benzotriazole or dicyclohexyl carbodiimide (DCC) mediated coupling reactions. The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity of the new compounds was assessed against four human (h) isoforms, hCA I, hCA II, hCA IX and hCA XII. Most of the synthesized compounds showed good in vitro carbonic anhydrase inhibitory properties, with inhibition constants in the low nanomolar range. Particularly, the new dipeptide-sulfonamide conjugates incorporating Ala, Phe and Met in the dipeptide sequence, showed the most effective inhibitory activity against to CA IX and XII.

摘要

二十四种新型磺酰胺衍生物通过苯并三唑或二环己基碳二亚胺（DCC）介导的偶联反应，由同磺酰苯胺的简便酰化反应合成。新化合物的碳酸酐酶（CA，EC 4.2.1.1）抑制活性针对四种人（h）同工酶 hCA I、hCA II、hCA IX 和 hCA XII 进行评估。大多数合成的化合物表现出良好的体外碳酸酐酶抑制特性，抑制常数在纳摩尔范围内。特别是，含有丙氨酸、苯丙氨酸和甲硫氨酸的新型二肽-磺酰胺缀合物对 CA IX 和 XII 表现出最有效的抑制活性。

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