The first synthesis of 4-phenylbutenone derivative bromophenols including natural products and their inhibition profiles for carbonic anhydrase,acetylcholinesterase and butyrylcholinesterase enzymes |
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| Institution: | 1. Department of Chemistry, Faculty of Sciences, Atatürk University, 25240, Erzurum, Turkey;2. Faculty of Health Sciences, Gümü?hane University, 29100, Gümü?hane, Turkey;3. Department of Chemistry, Faculty of Arts & Sciences, Marmara University, 34722, ?stanbul, Turkey;1. Department of Chemistry, Faculty of Science, Ataturk University, Erzurum 25240, Turkey;2. Dogubeyazit Ahmed-i Hani Vocational School, Agri Ibrahim Cecen University, Agri 04400, Turkey;3. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Bezmialem Vakif University, Istanbul 34093, Turkey;1. Sakarya University, Faculty of Science and Arts, Department of Chemistry, 54187 Serdivan Sakarya, Turkey;2. Department of Chemistry, Faculty of Science, Atatürk University, 25240 Erzurum, Turkey;3. Sakarya University, Faculty of Medicine, Infectious Diseases and Clinical Microbiology Department, 54290 Adapazar? Sakarya, Turkey;1. Department of Chemistry, Faculty of Science, Ataturk University, Erzurum 25240, Turkey;2. Dogubayazit Ahmed-i Hani Vocational School, Agri Ibrahim Cecen University, Agri 04400, Turkey;1. Erzurum Technical University, Faculty of Science, Department of Basic Sciences, Erzurum, Turkey;2. Ataturk University, Faculty of Science, Department of Chemistry, Erzurum, Turkey;3. King Saud University, College of Science, Department of Zoology, Riyadh, Saudi Arabia;4. Department of Biophysics, School of Medicine, Bahcesehir University, Istanbul, Turkey;5. Faculty of Science and Arts, Department of Chemistry, Sutcu Imam University, Kahramanmaras, Turkey;6. Dipartimento di Chimica Ugo Schiff, Universita degli Studi di Firenze, Sesto Fiorentino (Firenze), Italy;7. Neurofarba Department, Section of Pharmaceutical and Nutraceutical Sciences, Universita degli Studi di Firenze, Sesto Fiorentino (Florence), Italy |
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| Abstract: | The first synthesis of (E)-4-(3-bromo-4,5-dihydroxyphenyl)but-3-en-2-one (1), (E)-4-(2-bromo-4,5-dihydroxyphenyl)but-3-en-2-one (2), and (E)-4-(2,3-dibromo-4,5-dihydroxyphenyl)but-3-en-2-one (3) was realized as natural bromophenols. Derivatives with mono OMe of 2 and 3 were obtained from the reactions of their derivatives with di OMe with AlCl3. These novel 4-phenylbutenone derivatives were effective inhibitors of the cytosolic carbonic anhydrase I and II isoenzymes (hCA I and II), acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) with Ki values in the range of 158.07–404.16 pM for hCA I, 107.63–237.40 pM for hCA II, 14.81–33.99 pM for AChE and 5.64–19.30 pM for BChE. The inhibitory effects of the synthesized novel 4-phenylbutenone derivatives were compared to acetazolamide as a clinical hCA I and II isoenzymes inhibitor and tacrine as a clinical AChE and BChE enzymes inhibitor. |
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| Keywords: | Bromination Bromophenols Carbonic anhydrase Acetylcholinesterase Butyrylcholinesterase Enzyme inhibition Phenylbutenone Natural products |
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