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9,10‐Dibromo‐ N ‐aryl‐9,10‐dihydro‐9,10‐[3,4]epipyrroloanthracene‐12,14‐diones: Synthesis and Investigation of Their Effects on Carbonic Anhydrase Isozymes I, II, IX, and XII
Author(s) -
Göksu Haydar,
Topal Meryem,
Keskin Ali,
Gültekin Mehmet S.,
Çelik Murat,
Gülçin İlhami,
Tanc Muhammet,
Supuran Claudiu T.
Publication year - 2016
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201600047
Subject(s) - carbonic anhydrase , chemistry , isozyme , aryl , chemical synthesis , stereochemistry , enzyme , medicinal chemistry , biochemistry , organic chemistry , in vitro , alkyl
N ‐substituted maleimides were synthesized from maleic anhydride and primary amines. 1,4‐Dibromo‐dibenzo[e,h]bicyclo‐[2,2,2]octane‐2,3‐dicarboximide derivatives ( 4a–f ) were prepared by the [4+2] cycloaddition reaction of dibromoanthracenes with the N ‐substituted maleimide derivatives. The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory effects of the new derivatives were assayed against the human (h) isozymes hCA I, II, IX, and XII. All tested bicyclo dicarboximide derivatives exhibited excellent inhibitory effects in the nanomolar range, with K i values in the range of 117.73–232.87 nM against hCA I and of 69.74–111.51 nM against hCA II, whereas they were low micromolar inhibitors against hCA IX and XII.