The inhibitory effects of phenolic Mannich bases on carbonic anhydrase I and II isoenzymes |
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| Authors: | Cem Yamali Mehtap Tugrak Muhammet Tanc |
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| Institution: | 1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ataturk University, Erzurum, Turkey and;2. Polo Scientifico, Laboratorio Di Chimica Bioinorganica, Universita Degli Studi Di Firenze, Sesto Fiorentino, Italy;3. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ataturk University, Erzurum, Turkey and;4. Polo Scientifico, Laboratorio Di Chimica Bioinorganica, Universita Degli Studi Di Firenze, Sesto Fiorentino, Italy |
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| Abstract: | Phenolic mono Mannich bases 2-4-hydroxy-3-(aminomethyl)benzylidene]-2,3-dihydro-1H-inden-1-one (8–15)] and bis Mannich bases 2-4-hydroxy-3,5-bis(aminomethyl)benzylidene]-2, 3-dihydro-1H-inden-1-one (2–7)] were synthesized starting from 2-(4-hydroxybenzylidene)-2, 3-dihydro-inden-1-one (1). This study was designed in order to investigate the carbonic anhydrase (CA, EC 4.2.1.1) inhibitory properties of a library of compounds incorporating the phenol functional group. All prepared compounds showed a low inhibition percentages on both human (h) isoforms hCA I and hCA II compared to the reference sulfonamide acetazolamide. Mannich bases 2–15 had lower inhibition percentages than the compound 1 on hCA I and hCA II, except compound 14, which is a Mannich base derivative of dipropylamine, which had a similar inhibitory power as compound 1 on hCA II. All compounds synthesized 1–15 were 1.3–1.9 times more effective on hCA II comparing with the effectivenes of the compounds on hCA I. |
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| Keywords: | Carbonic anhydrase indanone Mannich bases phenol |
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