The synthesis of novel pyrazole-3,4-dicarboxamides bearing 5-amino-1,3,4-thiadiazole-2-sulfonamide moiety with effective inhibitory activity against the isoforms of human cytosolic carbonic anhydrase I and II |
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| Institution: | 1. Department of Chemistry, Faculty of Arts and Sciences, Dumlupinar University, 43100 Kutahya, Turkey;2. Department of Chemistry, Faculty of Arts and Sciences, Ahi Evran University, 40000 Kırşehir, Turkey;3. Department of Biochemistry, Faculty of Veterinary Sciences, Mustafa Kemal University, 31000 Hatay, Turkey;4. Department of Chemistry, Faculty of Sciences, Atatürk University, 25240 Erzurum, Turkey;5. Department of Chemistry, Faculty of Natural Sciences, Architecture and Engineering, Bursa Technical University, Osmangazi, 16200 Bursa, Turkey;1. Università degli Studi di Firenze, Polo Scientifico, Laboratorio di Chimica Bioinorganica, Rm. 188, Via della Lastruccia 3, 50019 Sesto Fiorentino (Florence), Italy;2. Department of Pharmacology, Faculty of Pharmacy, Bezmialem Vakif University, Vatan Caddesi, 34093 Fatih, Istanbul, Turkey;3. Università degli Studi di Firenze, NEUROFARBA Dept., Sezione di Farmacologia, Viale Pieraccini 6, 50139 Florence, Italy;4. Università degli Studi di Firenze, NEUROFARBA Dept., Sezione di Scienze Farmaceutiche, Via Ugo Schiff 6, 50019 Sesto Fiorentino (Florence), Italy;1. Department of Chemistry, Kurukshetra University, Kurukshetra 136119, India;2. Università degli Studi di Firenze, Laboratorio di Chimica Bioinorganica, Rm 188, and Neurofarba Department, Sezione di Scienze Farmaceutiche, Via U. Schiff 6, I-50019 Sesto Fiorentino (Firenze), Italy;1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Egyptian Russian University, Badr City, Cairo 11829, Egypt;2. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Kafrelsheikh University, Kafrelsheikh, P.O. Box 33516, Egypt;3. Department of NEUROFARBA, Section of Pharmaceutical and Nutraceutical Sciences, University of Florence, Polo Scientifico, Via U. Schiff 6, 50019, Sesto Fiorentino, Firenze, Italy;4. Department of Applied Organic Chemistry, National Research Center, Dokki, Cairo 12622, Egypt;5. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Cairo University, Kasr El-Aini Street, Cairo, P.O. Box 11562, Egypt;1. Health Services Vocational School, Igdır University, 76000 Igdır, Turkey;2. Department of Science, Faculty of Education, Muş Alparslan University, 49250 Muş, Turkey;3. Department of Chemistry, Faculty of Science, Ataturk University, 25240 Erzurum, Turkey;4. Department of Molecular Biology and Genetics, Faculty of Arts and Science, Kilis 7 Aralik University, 79000 Kilis, Turkey;1. Department NEUROFARBA – Pharmaceutical and Nutraceutical Section, University of Firenze, via Ugo Schiff 6, I-50019 Sesto Fiorentino, Firenze, Italy;2. Department of Life and Environmental Sciences – Unit of Pharmaceutical, Pharmacological and Nutraceutical Sciences, University of Cagliari, via Ospedale 72, I-09124 Cagliari, Italy;3. Department of Chemical and Pharmaceutical Sciences and LTTA, University of Ferrara, via Fossato di Mortara 17/19, I-44100 Ferrara, Italy;1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ataturk University, Erzurum 25240, Turkey;2. Meikai University Research Institute of Odontology (M-RIO), Sakado, Saitama 350-0283, Japan;3. Neurofarba Department, Sezione di Scienza Farmaceutiche e Nutraceutiche, Universita degli Studi di Firenze, Via U. Schiff 6, 50019 Sesto Fiorentino (Florence), Italy;4. Latvian Biomedical Research and Study Center, Ratsupites 1, Riga, Latvia;5. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Agri Ibrahim Cecen University, Agri 04100, Turkey |
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| Abstract: | A series of 1-(3-substituted-phenyl)-5-phenyl-N3,N4-bis(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3,4-dicarboxamides (4–15) were synthesized. The structures of these pyrazole-sulfonamides were confirmed by FT-IR, 1H NMR, 13C NMR and elemental analysis methods. Human cytosolic carbonic anhydrase (CA, EC 4.2.1.1) isozymes (hCA I and II) were purified from erythrocyte cells by affinity chromatography. The inhibitory effects of newly synthesized derivatives (4–15) were investigated in vitro on esterase activities of these isozymes. The Ki values were determined as 0.119–3.999 μM for hCA I and 0.084–0.878 μM for hCA II. The results showed that the compound 6 for hCA I and the compound 11 for hCA II had the highest inhibitory effect. Beside that, the compound 8 had the lowest inhibition effect on both isozymes. |
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| Keywords: | Pyrazole-3 4-dicarboxylic acid 1 3 4-Thiadiazole-2-sulfonamide Synthesis Antiglaucoma Inhibition Carbonic anhydrase |
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