Synthesis of 4-sulfamoylphenyl-benzylamine derivatives with inhibitory activity against human carbonic anhydrase isoforms I, II, IX and XII

Bioorganic & Medicinal Chemistry
Mustafa DurgunClaudiu T Supuran

Abstract

Imine derivatives were obtained by condensation of sulfanilamide with substituted aromatic aldehydes. The Schiff bases were thereafter reduced with sodium borohydride, leading to the corresponding amines, derivatives of 4-sulfamoylphenyl-benzylamine. These sulfonamides were investigated as inhibitors of the human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms hCA I and II (cytosolic isozymes), as well as hCA IX and XII (transmembrane, tumor-associated enzymes). We noted that the compounds incorporating secondary amine moieties showed a better inhibitory activity against all CA isozymes compared to the corresponding Schiff bases. Low nanomolar CA II, IX and XII inhibitors were detected, whereas the activity against hCA I was less potent. The secondary amines incorporating sulfonamide or similar zinc-binding groups, poorly investigated chemotypes for designing metalloenzyme inhibitors, may offer interesting opportunities in the field due to the facile preparation and possibility to explore a vast chemical space.

References

Dec 25, 2002·Medicinal Research Reviews·Claudiu T SupuranAngela Casini
Oct 27, 2004·Journal of Enzyme Inhibition and Medicinal Chemistry·Silvia PastorekovaClaudiu T Supuran
Oct 27, 2004·Journal of Enzyme Inhibition and Medicinal Chemistry· Mahmood-Ul-HassanClaudiu T Supuran
Jan 3, 2008·Nature Reviews. Drug Discovery·Claudiu T Supuran
Aug 6, 2011·Journal of Enzyme Inhibition and Medicinal Chemistry·Zahid H Chohan, Hazoor A Shad
Dec 8, 2011·Journal of Enzyme Inhibition and Medicinal Chemistry·Ramazan DemirdağClaudiu T Supuran
Apr 4, 2012·Journal of Enzyme Inhibition and Medicinal Chemistry·Claudiu T Supuran
Jan 17, 2013·Journal of Enzyme Inhibition and Medicinal Chemistry·Sonia Del PreteClemente Capasso
Feb 6, 2013·Journal of Enzyme Inhibition and Medicinal Chemistry·Claudiu T Supuran
Feb 16, 2013·Journal of Enzyme Inhibition and Medicinal Chemistry·Fortunato MigliardiniClemente Capasso
Mar 7, 2013·Expert Opinion on Therapeutic Patents·Claudiu T Supuran
May 1, 2013·Expert Opinion on Drug Discovery·Giuseppina De SimoneClaudiu T Supuran
May 1, 2013·Journal of Enzyme Inhibition and Medicinal Chemistry·Clemente Capasso, Claudiu T Supuran
Aug 7, 2013·Journal of Enzyme Inhibition and Medicinal Chemistry·Sonia Del PreteClemente Capasso
Jan 25, 2014·Journal of Enzyme Inhibition and Medicinal Chemistry·Sonia Del PreteClemente Capasso
Apr 29, 2014·Journal of Enzyme Inhibition and Medicinal Chemistry·Clemente Capasso, Claudiu T Supuran
Dec 2, 2015·Journal of Enzyme Inhibition and Medicinal Chemistry·Claudiu T Supuran

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Citations

Feb 28, 2019·Journal of Enzyme Inhibition and Medicinal Chemistry·Ismail KoyuncuClaudiu T Supuran
Oct 27, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Suleyman AkocakClaudiu T Supuran
Apr 7, 2020·Journal of Enzyme Inhibition and Medicinal Chemistry·Mustafa DurgunClaudiu T Supuran
Mar 12, 2021·Journal of Biomolecular Structure & Dynamics·Seyit Ali GüngörSultan Erkan
Jul 3, 2021·International Journal of Molecular Sciences·Ebru TemizClaudiu T Supuran

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