Design,synthesis, and carbonic anhydrase inhibition activity of benzenesulfonamide-linked novel pyrazoline derivatives |
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| Institution: | 1. Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia;2. Università degli Studi di Firenze, NEUROFARBA Dept., Sezione di Scienze Farmaceutiche, Via Ugo Schiff 6, 50019 Sesto Fiorentino, Florence, Italy;3. Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura, Egypt;1. Saint Petersburg State University, Saint Petersburg 199034, Russian Federation;2. Department of Organic Chemistry, Faculty of Science, RUDN University, 117198, Russian Federation;3. The Ushinsky Yaroslavl State Pedagogical University, Yaroslavl 150000, Russian Federation;4. Department of Pharmacy, University of Pisa, 56126 Pisa, Italy;5. Neurofarba Department, Universita degli Studi di Firenze, Florence, Italy;1. Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia;2. Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt;3. Department of Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo 11884, Egypt;4. NEUROFARBA Department – Pharmaceutical and Nutraceutical Section, Laboratory of Molecular Modeling Cheminformatics & QSAR University of Florence, Via Ugo Schiff 6, 50019 Sesto Fiorentino, Florence, Italy;5. NEUROFARBA Department – Pharmaceutical and Nutraceutical Section, University of Florence, Via Ugo Schiff 6, 50019 Sesto Fiorentino, Florence, Italy;1. Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia;2. Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt;3. Department of Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo 11884, Egypt;4. NEUROFARBA Department, University of Florence, Via Ugo Schiff 6, 50019 Sesto Fiorentino (Florence), Italy;1. Department of Chemistry of Natural and Microbial Products, Division of Pharmaceutical and Drug Industries Research, National Research Centre, El‐Buhouth St., Dokki, P.O. Box 12622, Cairo, Egypt;2. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Cairo University, Kasr El-Aini Street, Cairo, P.O. Box 11562, Egypt;3. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, New Giza University, New Giza, Km 22 Cairo–Alexandria Desert Road, Cairo, Egypt;4. Università degli Studi di Firenze, Department NEUROFARBA – Pharmaceutical and Nutraceutical Section, University of Firenze, Via Ugo Schiff 6, I-50019, Sesto Fiorentino, Firenze, Italy;5. Helmholtz Institute for Pharmaceutical Research Saarland (HIPS) – Helmholtz Centre for Infection Research (HZI), Department of Drug Design and Optimization, Campus Building E8.1, 66123 Saarbrücken, Germany;1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Agri Ibrahim Cecen University, Agri, Turkey;2. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ataturk University, Erzurum, Turkey;3. Division of Pharmacology, Meikai University School of Dentistry, Saitama, Sakado, Japan;4. Meikai University Research Institute of Odontology (M-RIO), Meikai University School of Dentistry, Saitama, Sakado, Japan;5. Department of Chemistry, Faculty of Science, Ataturk University, Erzurum, Turkey;6. Department of Zoology, College of Science, King Saud University, Riyadh, Saudi Arabia;7. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Gazi University, Ankara, Turkey;8. Neurofarba Department e Laboratorio di Chimica Bioinorganica, Universita Degli Studi di Firenze, Sesto Fiorentino (Florence), Italy;1. Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia;2. Università degli Studi di Firenze, Dipartimento Neurofarba, Sezione di Scienze Farmaceutiche e Nutraceutiche, Via U. Schiff 6, 50019 Sesto Fiorentino, Florence, Italy;3. Department of Pharmaceutical Chemistry, College of Pharmacy, Prince Sattam Bin Abdulaziz University, AlKharj, Saudi Arabia;4. Department of Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo, Egypt;5. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo, Egypt |
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| Abstract: | Carbonic anhydrases (CA, EC 4.2.1.1) are Zinc metalloenzymes and are present throughout most living organisms. Among the catalytically active isoforms are the cytosolic CA I and II, and tumor-associated CA IX and CA XII. The carbonic anhydrase (CA) inhibitory activities of newly synthesized pyrazoline-linked benzenesulfonamides 18–33 against human CA (hCA) isoforms I, II, IX, and XII were measured and compared with that of acetazolamide (AAZ), a standard inhibitor. Potent inhibitory activity against hCA I was exerted by compounds 18–25, with inhibition constant (KI) values of 87.8–244.1 nM, which were greater than that of AAZ (KI, 250.0 nM). Compounds 19, 21, 22, 29, 30, and 32 were proven to have inhibitory activities against hCA IX with KI values (5.5–37.0 nM) that were more effective than or nearly equal to that of AAZ (KI, 25.0 nM). Compounds 20–22, and 30 exerted potent inhibitory activities (KIs, 7.1–10.1 nM) against hCA XII, in comparison with AAZ (KI, 5.7 nM). |
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| Keywords: | Synthesis Pyrazoline scaffolds Benzenesulfonamide Carbonic anhydrase Enzyme inhibition Acetazolamide |
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