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Superacid synthesis of halogen containing N-substituted-4-aminobenzene sulfonamides: new selective tumor-associated carbonic anhydrase inhibitors.
Bioorg Med Chem. 2013 Mar 15; 21(6):1555-63.BM

Abstract

A series of new, halogen containing N-substituted 4-aminobenzenesulfonamides were synthesized by using superacid HF/SbF5 chemistry and investigated as inhibitors of several human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms, that is, the cytosolic hCA I and II and, the tumor-associated transmembrane isoforms hCA IX and XII. Despite the substitution of the sulfonamide function, the presence of fluorine atom(s) in β position of the sulfonamide function strongly favors hCA inhibition. A similar effect of the β-fluorinated alkyl substitution on the amino function has been also observed. Among the tested compounds, several chlorinated derivatives have been identified as selective nanomolar, tumor-associated isoforms inhibitors. These non-primary sulfonamides probably bind in the coumarin-binding site, at the entrance of the cavity, and not to the metal ion as the primary sulfonamide inhibitors.

Authors+Show Affiliations

Superacid group in « Glycochimie, Superacide et Chimie des systèmes » team-Université de Poitiers, CNRS UMR 7285 IC2MP, 4, avenue Michel Brunet, F-86022 Poitiers Cedex, France.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

22705188

Citation

Compain, Guillaume, et al. "Superacid Synthesis of Halogen Containing N-substituted-4-aminobenzene Sulfonamides: New Selective Tumor-associated Carbonic Anhydrase Inhibitors." Bioorganic & Medicinal Chemistry, vol. 21, no. 6, 2013, pp. 1555-63.
Compain G, Martin-Mingot A, Maresca A, et al. Superacid synthesis of halogen containing N-substituted-4-aminobenzene sulfonamides: new selective tumor-associated carbonic anhydrase inhibitors. Bioorg Med Chem. 2013;21(6):1555-63.
Compain, G., Martin-Mingot, A., Maresca, A., Thibaudeau, S., & Supuran, C. T. (2013). Superacid synthesis of halogen containing N-substituted-4-aminobenzene sulfonamides: new selective tumor-associated carbonic anhydrase inhibitors. Bioorganic & Medicinal Chemistry, 21(6), 1555-63. https://doi.org/10.1016/j.bmc.2012.05.037
Compain G, et al. Superacid Synthesis of Halogen Containing N-substituted-4-aminobenzene Sulfonamides: New Selective Tumor-associated Carbonic Anhydrase Inhibitors. Bioorg Med Chem. 2013 Mar 15;21(6):1555-63. PubMed PMID: 22705188.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Superacid synthesis of halogen containing N-substituted-4-aminobenzene sulfonamides: new selective tumor-associated carbonic anhydrase inhibitors. AU - Compain,Guillaume, AU - Martin-Mingot,Agnès, AU - Maresca,Alfonso, AU - Thibaudeau,Sebastien, AU - Supuran,Claudiu T, Y1 - 2012/05/26/ PY - 2012/03/29/received PY - 2012/05/09/revised PY - 2012/05/15/accepted PY - 2012/6/19/entrez PY - 2012/6/19/pubmed PY - 2013/9/5/medline SP - 1555 EP - 63 JF - Bioorganic & medicinal chemistry JO - Bioorg. Med. Chem. VL - 21 IS - 6 N2 - A series of new, halogen containing N-substituted 4-aminobenzenesulfonamides were synthesized by using superacid HF/SbF5 chemistry and investigated as inhibitors of several human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms, that is, the cytosolic hCA I and II and, the tumor-associated transmembrane isoforms hCA IX and XII. Despite the substitution of the sulfonamide function, the presence of fluorine atom(s) in β position of the sulfonamide function strongly favors hCA inhibition. A similar effect of the β-fluorinated alkyl substitution on the amino function has been also observed. Among the tested compounds, several chlorinated derivatives have been identified as selective nanomolar, tumor-associated isoforms inhibitors. These non-primary sulfonamides probably bind in the coumarin-binding site, at the entrance of the cavity, and not to the metal ion as the primary sulfonamide inhibitors. SN - 1464-3391 UR - https://www.unboundmedicine.com/medline/citation/22705188/Superacid_synthesis_of_halogen_containing_N_substituted_4_aminobenzene_sulfonamides:_new_selective_tumor_associated_carbonic_anhydrase_inhibitors_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0968-0896(12)00411-7 DB - PRIME DP - Unbound Medicine ER -