Synthesis,characterization, anticancer,antimicrobial and carbonic anhydrase inhibition profiles of novel (3aR,4S,7R,7aS)-2-(4-((E)-3-(3-aryl)acryloyl) phenyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione derivatives |
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Affiliation: | 1. Cumhuriyet University, Vocational School of Health Services, 58140 Sivas, Turkey;2. Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpasa University, 60250 Tokat, Turkey;3. Department of Molecular Biology and Genetics, Faculty of Arts and Sciences, Gaziosmanpasa University, 60250 Tokat, Turkey;4. Department of Chemistry, Faculty of Science, Atatürk University, 25240 Erzurum, Turkey;5. Department of Zoology, College of Science, King Saud University, Riyadh, Saudi Arabia;1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ataturk University, Erzurum, Turkey;2. Division of Biochemistry, Meikai University School of Dentistry, Sakado, Saitama, Japan;3. Meikai University Research Institute of Odontology (M-RIO), Meikai University School of Dentistry, Sakado, Saitama, Japan;4. Faculty of Science, Department of Chemistry, Ataturk University, Erzurum, Turkey;5. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu University, Eskişehir, Turkey;6. Neurofarba Department, Sezione di Scienza Farmaceutiche e Nutraceutiche, Universita egli Studi di Firenze, Via U. Schiff 6, 50019 Sesto Fiorentino (Florence), Italy;1. Ataturk University, Faculty of Science, Department of Chemistry, Erzurum, Turkey;2. Erzurum Technical University, Faculty of Science, Department of Basic Sciences, Erzurum, Turkey;3. Agri Ibrahim Cecen University, Central Researching Laboratory, 04200 Agri, Turkey;4. Department of Zoology, College of Science, King Saud University, Riyadh, Saudi Arabia;5. Department of Biophysics, School of Medicine, Bahcesehir University, Istanbul, Turkey;6. Department of chemistry, Istanbul Technical University, Istanbul, Turkey;1. Pharmaceutical Chemistry Department, Faculty of Pharmacy, Cairo University, Cairo 11562, Egypt;2. University of Florence, Department of NEUROFARBA, Section of Pharmaceutical and Nutraceutical Sciences, via Ugo Schiff 6, 50019 Sesto Fiorentino, Florence, Italy;1. Agri Ibrahim Cecen University, Central Researching Laboratory, 04100 Agri, Turkey;2. Atatürk University, Faculty of Science, Department of Chemistry, Erzurum, Turkey;3. Agri Ibrahim Cecen University, Faculty of Arts and Science, Agri, Turkey;4. Igdir University, Vocational School of Health Services, Department of Medical Services and Techniques, Igdir, Turkey;1. Tercan Vocational High School, Erzincan Binali Yildirim University, Erzincan 24800, Turkey;2. Department of Chemistry, Faculty of Science, Atatürk University, Erzurum 25240, Turkey;3. Department of Pharmaceutical Basic Sciences, Faculty of Pharmacy, Erzincan Binali Yildirim University, Erzincan 24100, Turkey;4. Central Research and Application Laboratory, Agri Ibrahim Cecen University, Agri 04100, Turkey;5. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Mersin University, Mersin 33169, Turkey;1. University of Kahramanmaraş Sütçü Imam, Faculty of Science and Arts, Department of Chemistry, 46100 Kahramanmaraş, Turkey;2. Atatürk University, Faculty of Science, Department of Chemistry, 25240 Erzurum, Turkey;3. Agri Ibrahim Cecen University Central Research and Application Laboratory, 04100 Agri, Turkey;4. Inonu University, Faculty of Science, Department of Chemistry, 44280 Malatya, Turkey;5. Department of Biotechnology, Faculty of Science, Bartin University, 74100 Bartin, Turkey;6. Department of Molecular Biology and Genetics, Faculty of Arts and Science, Kilis 7 Aralık University, 79000 Kilis, Turkey |
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Abstract: | In the present study, a series of new hybrid compounds containing chalcone and methanoisoindole units 7a-n ((3aR,4S,7R,7aS)-2-(4-((E)-3-(3-aryl)acryloyl) phenyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione) were synthesized, characterized and investigated for their anticancer activity against C6 gliocarcinoma cell in rats, and antimicrobial activity against some human pathogen microorganisms. The compounds 7e, 7h, 7j, 7k, 7L and 7n showed very high anticancer activity with the inhibition range of 80.51–97.02% compared to 5-FU. Some of the compounds exhibited anti-microbial activity. Also, they evaluated for inhibition effects against human carbonic anhydrase I, and II isoenzymes (hCA I and II) with Ki values in the range of 405.26–635.68 pM for hCA I, and 245.40–489.60 pM for hCA II, respectively. These results demonstrated that 3aR,4S,7R,7aS)-2-(4-((E)-3-(3-aryl)acryloyl)phenyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione derivatives could be used in different biomedical applications. |
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Keywords: | Chalcone Isoindole Anticancer C6 Antimicrobial Carbonic anhydrase |
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