Synthesis of novel 5-amino-1,3,4-thiadiazole-2-sulfonamide containing acridine sulfonamide/carboxamide compounds and investigation of their inhibition effects on human carbonic anhydrase I,II, IV and VII |
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| Institution: | 1. Chemistry Department, Faculty of Arts and Science, Dumlup?nar University, 43100 Kütahya, Turkey;2. Università degli Studi di Firenze, NEUROFARBA Dept., Sezione di Scienze Farmaceutiche e Nutraceutiche, 50019 Sesto Fiorentino, Florence, Italy;3. Biochemistry Department, Faculty of Arts and Science, Dumlup?nar University, 43100 Kütahya, Turkey;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. Center for Biomaterials, Korea Institute of Science and Technology, PO Box 131, Cheongryang, Seoul 130-650, Republic of Korea;2. Department of Biomolecular Science, University of Science and Technology, 113 Gwahangno, Yuseong-gu, Daejeon 305-333, Republic of Korea;3. Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki-Giza 12622, Egypt;4. Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt;5. Chemical Kinomics Research Center, Korea Institute of Science and Technology, PO Box 131, Cheongryang, Seoul 130-650, Republic of Korea;1. Latvian Institute of Organic Synthesis, 21 Aizkraukles Str., Riga LV-1006, Latvia;2. Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3/7 Paula Valdena Str., Riga LV-1048, Latvia;3. Latvian Biomedical Research and Study Center, Rātsupītes 1, LV-1067 Riga, Latvia;4. Università degli Studi di Firenze, Dipartimento di Chimica, Laboratorio di Chimica Bioinorganica, Polo Scientifico, Via della Lastruccia 3, 50019 Sesto Fiorentino, Florence, Italy;5. Faculty of Biology, Department of Molecular Biology, University of Latvia, Jelgavas 1, LV1004 Riga, Latvia;6. Università degli Studi di Firenze, Dipartimento Neurofarba, Sezione di ScienzeFarmaceutiche e Nutraceutiche, Via U. Schiff 6, 50019 Sesto Fiorentino, Florence, Italy;1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Cairo University, Kasr El-Aini Street, Cairo, P.O. Box, 11562, Egypt;2. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Al-Azhar University, Assiut, 71524, Egypt;3. National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS, 38677, USA;4. Pharmacognosy Department, National Research Center, Dokki, Giza, 12622, Egypt;1. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran;2. Department of Chemistry, Shiraz University of Technology, Shiraz, Iran;3. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy and Biotechnology Research Center, Tehran University of Medical Sciences, Iran;4. School of Chemistry, College of Science, University of Tehran, Tehran, Iran;5. Department of Biotechnology, Iranian Research Organization for Science and Technology (IROST), Tehran, Iran;6. Diabetes Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran;7. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran;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 |
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| Abstract: | Herein, we report that acridine intermediates 5 were obtained from the reduction of nitro acridine derivatives 4, which were synthesized via condensation of dimedone, p-nitrobenzaldehyde with 4-amino-N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)benzamide, respectively. Then acridine sulfonamide/carboxamide (7a–i) compounds were synthesized by reaction of amino acridine 5 with sulfonyl chlorides and carbamoyl chlorides. The new compounds were characterized by melting points, FT-IR, 1H NMR, 13C NMR and HRMS analyzes. The evaluation of in vitro test of the synthesized compounds against hCA I, II, IV and VII showed that some of them are potent inhibitors. Among them, compound 7e showed the most potent activity against hCA II with a KI of 7.9 nM. |
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| Keywords: | Carbonic anhydrase Acridine Sulfonamide Carboxamide Enzyme inhibition Isoforms CA I II IV and VII |
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