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Cited by 189

The DOI matches its Crossref record; 2 of the 2 references it cites were found in a registry or an index.

Carbonic Anhydrase Inhibitors: Inhibition of Isozymes I, II, and IX with Triazole-Linked O-Glycosides of Benzene Sulfonamides

Open access
Wilkinson, Brendan L., Bornaghi, Laurent F., Houston, Todd A., Innocenti, Alessio, Vullo, Daniela, Supuran, Claudiu T., Poulsen, Sally-Ann·2007·Journal of Medicinal Chemistry

Abstract

We report the synthesis of a series of benzene sulfonamides containing triazole-O-glycoside tails for evaluation as carbonic anhydrase (CA) inhibitors. These glycoconjugates were synthesized by the 1,3-dipolar cycloaddition reaction of 4-azidobenzenesulfonamide with O-propynyl glycosides. Compounds were assessed for their ability to inhibit the enzymatic activity of the physiologically dominant isozymes hCA I and II and the tumor-associated isozyme hCA IX (h = human). Against hCA I these compounds were either micromolar or low-nanomolar inhibitors, while against hCA II and IX inhibition in the range of 6.8-53 and 9.7-107 nM, respectively, was observed. The most potent inhibitor against hCA IX was the galactose derivative 8 (Ki = 9.7 nM); this is so far the most potent glycoconjugate inhibitor reported for the tumor-associated hCA IX. These carbohydrate-tethered sulfonamides may prove interesting lead candidates to target tumor-associated CA isozymes, wherein the CA domain is located extracellularly.

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Crossref · 10.1021/jm061320h

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Metadata

Authors
Wilkinson, B. L., Bornaghi, L. F., Houston, T. A., Innocenti, A., Vullo, D., Supuran, C. T., & Poulsen, S.-A.
Venue
Journal of Medicinal Chemistry
Published
2007-03-08
Volume
50
Issue
7
Pages
1651-1657
ISSN
  • 0022-2623 (ISSN-L)
  • 1520-4804
OpenAlex
W2009420676
Cited by
189
References
2
FWCI
3.83
Type
journal article
Language
en
Open access
green

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