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
| Autor: | Murat Çelik, İlhami Gülçin, Meryem Topal, Muhammet Tanc, Mehmet Serdar Gültekin, Claudiu T. Supuran, Ali Keskin, Haydar Göksu |
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| Rok vydání: | 2016 |
| Předmět: |
biology
Bicyclic molecule 010405 organic chemistry Stereochemistry Aryl Pharmaceutical Science Maleic anhydride 01 natural sciences Isozyme Cycloaddition 0104 chemical sciences 010404 medicinal & biomolecular chemistry chemistry.chemical_compound Enzyme inhibition chemistry Carbonic anhydrase Drug Discovery biology.protein Maleimide |
| Zdroj: | Archiv der Pharmazie. 349:466-474 |
| ISSN: | 0365-6233 |
| DOI: | 10.1002/ardp.201600047 |
| Popis: | 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 Ki 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. |
| Databáze: | OpenAIRE |
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