6-Substituted Triazolyl Benzoxaboroles as Selective Carbonic Anhydrase Inhibitors: In Silico Design, Synthesis, and X-ray Crystallography
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6-Substituted Triazolyl Benzoxaboroles as Selective Carbonic Anhydrase Inhibitors: In Silico Design, Synthesis, and X-ray Crystallography (67 views)

Nocentini A, Bonardi A, Bazzicalupi C, Alterio V, Esposito D, Monti SM, Smietana M, De Simone G, Supuran CT, Gratteri P, Winum JY

J Med Chem (ISSN: 0022-2623linking), 2023 Jun 22; 66 (12 ): 8118-8129.

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Paper type: Journal Article , Research Support, Non-U. S. Gov'T

Impact factor: 0, 5-year impact factor: 0

Url: Not available.

Keywords: Carbonic Anhydrases Metabolism , Carbonic Anhydrase Ix Metabolism , Carbonic Anhydrase I Metabolism , Carbonic Anhydrase Ii Metabolism , Carbonic Anhydrase Inhibitors Chemistry , Crystallography, X-Ray , Structure-Activity Relationship , Antigens, Neoplasm Chemistry

Affiliations:
*** IBB - CNR ***

NEUROFARBA Department, Pharmaceutical and Nutraceutical Section, University of Florence, Via U. Schiff 6, 50019 Sesto Fiorentino, Firenze, Italy.
Department of Chemistry "Ugo Schiff", University of Florence, Via della Lastruccia 3-13, 50019 Sesto Fiorentino, Italy.
Institute of Biostructures and Bioimaging, Consiglio Nazionale delle Ricerche, Via Pietro Castellino, 111, 80131 Naples, Italy.
IBMM, Univ Montpellier, CNRS, ENSCM, 1919 route de Mende, 34293 Montpellier, cedex 5, France.


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6-Substituted Triazolyl Benzoxaboroles as Selective Carbonic Anhydrase Inhibitors: In Silico Design, Synthesis, and X-ray Crystallography

Benzoxaborole is currently a scaffold of great relevance in medicinal chemistry. In 2016, it was reported to be a new and valuable chemotype for designing carbonic anhydrase (CA) inhibitors. Herein, using an in silico design, we report the synthesis and characterization of substituted 6-(1H-1,2,3-triazol-1-yl)benzoxaboroles. 6-Azidobenzoxaborole was described for the first time as a molecular platform to prepare libraries of inhibitors by a copper(I)-catalyzed azide-alkyne cycloaddition via a click chemistry strategy. With inhibition constants below 30 nM, some derivatives, such as compound 20, showed efficacy as selective hCA VII and IX inhibitors. The design hypothesis was validated by crystallographic investigation on the hCA II/20 adduct, which provided explanations over the different inhibition behavior observed against the five evaluated hCA isoforms. Overall, this study identified 20 as a new promising lead compound to develop novel anticancer agents targeting the tumor-associated hCA IX but also potent neuropathic pain relievers targeting hCA VII.
6-Substituted Triazolyl Benzoxaboroles as Selective Carbonic Anhydrase Inhibitors: In Silico Design, Synthesis, and X-ray Crystallography

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6-Substituted Triazolyl Benzoxaboroles as Selective Carbonic Anhydrase Inhibitors: In Silico Design, Synthesis, and X-ray Crystallography

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Di Fiore A, Supuran CT, Scaloni A, De Simone G
* Post-translational modifications in tumor-associated carbonic anhydrases (90 views)
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De Simone G, Bua S, Supuran CT, Alterio V
* Benzyl alcohol inhibits carbonic anhydrases by anchoring to the zinc coordinated water molecule (87 views)
Biochem Biophys Res Commun (ISSN: 0006-291xlinking), 2021 Apr 9; 548: 217-221.
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Nocentini A, Alterio V, Bua S, Micheli L, Esposito D, Buonanno M, Bartolucci G, Osman SM, Alothman ZA, Cirilli R, Pierini M, Monti SM, Di Cesare Mannelli L, Gratteri P, Ghelardini C, De Simone G, Supuran CT
* Phenyl(thio)phosphon(amid)ate Benzenesulfonamides as Potent and Selective Inhibitors of Human Carbonic Anhydrases II and VII Counteract Allodynia in a Mouse Model of Oxaliplatin-Induced Neuropathy (230 views)
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Impact Factor: 6.205
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Langella E, Alterio V, D'Ambrosio K, Cadoni R, Winum JY, Supuran CT, Monti SM, De Simone G, Di Fiore A
* Exploring benzoxaborole derivatives as carbonic anhydrase inhibitors: a structural and computational analysis reveals their conformational variability as a tool to increase enzyme selectivity (310 views)
J Enzym Inhib Med Ch (ISSN: 1475-6366linking, 1475-6374electronic), 2019 Dec; 34(1): 1498-1505.
Impact Factor: 4.027
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Mishra CB, Kumari S, Angeli A, Bua S, Buonanno M, Monti SM, Tiwari M, Supuran CT
* Discovery of potent anti-convulsant carbonic anhydrase inhibitors: Design, synthesis, in vitro and in vivo appraisal (291 views)
Eur J Med Chem (ISSN: 0223-5234linking, 1768-3254electronic), 2018 Aug 5; 156: 430-443.
Impact Factor: 4.816
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Rami M, Dubois L, Parvathaneni NK, Alterio V, van Kuijk SJ, Monti SM, Lambin P, De Simone G, Supuran CT, Winum JY
* Hypoxia-targeting carbonic anhydrase IX inhibitors by a new series of nitroimidazole-sulfonamides/sulfamides/sulfamates (629 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2013 Nov 14; 56(21): 8512-8520.
Impact Factor: 5.48
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6 Records (6 excluding Abstracts).
Total impact factor: 27.563 (27.563 excluding Abstracts).
Total 5 year impact factor: 21.914 (21.914 excluding Abstracts).

Last modified by Davide Esposito on Friday 04 August 2023, 14:53:27
67 views. Last view on Monday 07 October 2024, 5:57:55