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Journal of Enzyme Inhibition and Medicinal Chemistry Volume 32, 2017 - Issue 1
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Research Article

Primary mono- and bis-sulfonamides obtained via regiospecific sulfochlorination of N-arylpyrazoles: inhibition profile against a panel of human carbonic anhydrases

Mikhail KrasavinSaint Petersburg State University, Saint Petersburg, Russian Federation; Correspondence[email protected]
ORCID Iconhttp://orcid.org/0000-0002-0200-4772View further author information
ORCID Icon,
Mikhail KorsakovThe Ushinsky Yaroslavl State Pedagogical University, Yaroslavl, Russian Federation; View further author information
,
Oksana RonzhinaThe Ushinsky Yaroslavl State Pedagogical University, Yaroslavl, Russian Federation; View further author information
,
Tiziano TuccinardiDepartment of Pharmacy, University of Pisa, Pisa, Italy; ORCID Iconhttp://orcid.org/0000-0002-6205-4069View further author information
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Stanislav KalininSaint Petersburg State University, Saint Petersburg, Russian Federation; View further author information
,
Muhammet TançDepartment of Neurofarba, Universita degli Studi di Firenze, Florence, ItalyView further author information
&
Claudiu T. SupuranDepartment of Neurofarba, Universita degli Studi di Firenze, Florence, ItalyCorrespondence[email protected]
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Pages 920-934 | Received 20 May 2017, Accepted 15 Jun 2017, Published online: 18 Jul 2017

Citations (17)

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Claudiu T. Supuran. (2020) Exploring the multiple binding modes of inhibitors to carbonic anhydrases for novel drug discovery. Expert Opinion on Drug Discovery 15:6, pages 671-686.
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Siham A. Alissa, Hanan A. Alghulikah, Zeid A. Alothman, Sameh M. Osman, Sonia Del Prete, Clemente Capasso, Alessio Nocentini & Claudiu T. Supuran. (2020) Phosphonamidates are the first phosphorus-based zinc binding motif to show inhibition of β-class carbonic anhydrases from bacteria, fungi, and protozoa. Journal of Enzyme Inhibition and Medicinal Chemistry 35:1, pages 59-64.
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Alessio Nocentini & Claudiu T. Supuran. (2019) Advances in the structural annotation of human carbonic anhydrases and impact on future drug discovery. Expert Opinion on Drug Discovery 14:11, pages 1175-1197.
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Mohammad M. Al-Sanea, Ahmed Elkamhawy, Sora Paik, Silvia Bua, So Ha Lee, Mohamed A. Abdelgawad, Eun Joo Roh, Wagdy M. Eldehna & Claudiu T. Supuran. (2019) Synthesis and biological evaluation of novel 3-(quinolin-4-ylamino)benzenesulfonamides as carbonic anhydrase isoforms I and II inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry 34:1, pages 1457-1464.
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Suleyman Akocak, Nabih Lolak, Silvia Bua, Alessio Nocentini & Claudiu T. Supuran. (2019) Activation of human α-carbonic anhydrase isoforms I, II, IV and VII with bis-histamine schiff bases and bis-spinaceamine substituted derivatives. Journal of Enzyme Inhibition and Medicinal Chemistry 34:1, pages 1193-1198.
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Baijayantimala Swain, Andrea Angeli, Srinivas Angapelly, Pavitra S. Thacker, Priti Singh, Claudiu T. Supuran & Mohammed Arifuddin. (2019) Synthesis of a new series of 3-functionalised-1-phenyl-1,2,3-triazole sulfamoylbenzamides as carbonic anhydrase I, II, IV and IX inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry 34:1, pages 1199-1209.
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Alessandra Ammazzalorso, Simone Carradori, Andrea Angeli, Atilla Akdemir, Barbara De Filippis, Marialuigia Fantacuzzi, Letizia Giampietro, Cristina Maccallini, Rosa Amoroso & Claudiu T. Supuran. (2019) Fibrate-based N-acylsulphonamides targeting carbonic anhydrases: synthesis, biochemical evaluation, and docking studies. Journal of Enzyme Inhibition and Medicinal Chemistry 34:1, pages 1051-1061.
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Articles from other publishers (10)

Panasa Mahesh, Parameswari Akshinthala, Naresh Kumar Katari, Lavleen Kumar Gupta, Dikshita Panwar, Manoj Kumar Sharma, Sreekantha Babu Jonnalagadda & Rambabu Gundla. (2023) Antiproliferative Activity of New Pyrazole-4-sulfonamide Derivatives: Synthesis and Biological Evaluation. ACS Omega 8:29, pages 25698-25709.
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Nikolina Sibinčić, Stanislav Kalinin, Vladimir Sharoyko, Julia Efimova, Olga A. Gasilina, Mikhail Korsakov, Maxim Gureev & Mikhail Krasavin. (2023) A Series of Trifluoromethylisoxazolyl- and Trifluoromethylpyrazolyl- Substituted (Hetero)aromatic Sulfonamide Carbonic Anhydrase Inhibitors: Synthesis, and Convenient Prioritization Workflow for Further In Vivo Studies. Medicinal Chemistry 19:2, pages 193-210.
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Reihane Ghomashi, Shakila Ghomashi, Hamidreza Aghaei & Ahmad Reza Massah. (2023) Recent Advances in Biological Active Sulfonamide based Hybrid Compounds Part A: Two-Component Sulfonamide Hybrids. Current Medicinal Chemistry 30:4, pages 407-480.
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Karol Biernacki, Mateusz Daśko, Olga Ciupak, Konrad Kubiński, Janusz Rachon & Sebastian Demkowicz. (2020) Novel 1,2,4-Oxadiazole Derivatives in Drug Discovery. Pharmaceuticals 13:6, pages 111.
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Stanislav Kalinin, Alessio Nocentini, Alexander Kovalenko, Vladimir Sharoyko, Alessandro Bonardi, Andrea Angeli, Paola Gratteri, Tatiana B. Tennikova, Claudiu T. Supuran & Mikhail Krasavin. (2019) From random to rational: A discovery approach to selective subnanomolar inhibitors of human carbonic anhydrase IV based on the Castagnoli-Cushman multicomponent reaction. European Journal of Medicinal Chemistry 182, pages 111642.
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Mikhail Krasavin, Anton Shetnev, Sergey Baykov, Stanislav Kalinin, Alessio Nocentini, Vladimir Sharoyko, Giulio Poli, Tiziano Tuccinardi, Mikhail Korsakov, Tatiana B. Tennikova & Claudiu T. Supuran. (2019) Pyridazinone-substituted benzenesulfonamides display potent inhibition of membrane-bound human carbonic anhydrase IX and promising antiproliferative activity against cancer cell lines. European Journal of Medicinal Chemistry 168, pages 301-314.
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Mikhail Krasavin, Anton Shetnev, Tatyana Sharonova, Sergey Baykov, Stanislav Kalinin, Alessio Nocentini, Vladimir Sharoyko, Giulio Poli, Tiziano Tuccinardi, Sofia Presnukhina, Tatiana B. Tennikova & Claudiu T. Supuran. (2019) Continued exploration of 1,2,4-oxadiazole periphery for carbonic anhydrase-targeting primary arene sulfonamides: Discovery of subnanomolar inhibitors of membrane-bound hCA IX isoform that selectively kill cancer cells in hypoxic environment. European Journal of Medicinal Chemistry 164, pages 92-105.
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Edita Čapkauskaitė, Asta Zubrienė, Vaida Paketurytė, David D. Timm, Sigitas Tumkevičius & Daumantas Matulis. (2018) Thiazole-substituted benzenesulfonamides as inhibitors of 12 human carbonic anhydrases. Bioorganic Chemistry 77, pages 534-541.
Crossref
Alexander Sapegin, Stanislav Kalinin, Andrea Angeli, Claudiu T. Supuran & Mikhail Krasavin. (2018) Unprotected primary sulfonamide group facilitates ring-forming cascade en route to polycyclic [1,4]oxazepine-based carbonic anhydrase inhibitors. Bioorganic Chemistry 76, pages 140-146.
Crossref
Mikhail Krasavin, Anton Shetnev, Tatyana Sharonova, Sergey Baykov, Tiziano Tuccinardi, Stanislav Kalinin, Andrea Angeli & Claudiu T. Supuran. (2018) Heterocyclic periphery in the design of carbonic anhydrase inhibitors: 1,2,4-Oxadiazol-5-yl benzenesulfonamides as potent and selective inhibitors of cytosolic hCA II and membrane-bound hCA IX isoforms. Bioorganic Chemistry 76, pages 88-97.
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