Inhibition of carbonic anhydrases from the extremophilic bacteria Sulfurihydrogenibium yellostonense (SspCA) and S. azorense (SazCA) with a new series of sulfonamides incorporating aroylhydrazone-, [1,2,4]triazolo[3,4-b][1,3,4]thiadiazinyl- or 2-(cyanophenylmethylene)-1,3,4-thiadiazol-3(2H)-yl moieties

Bioorganic & Medicinal Chemistry
Ahmed M AlafeefyClaudiu T Supuran

Abstract

A series of new sulfonamides was prepared starting from 2-oxo-N'-(4-sulfamoylphenyl)-propanehydrazonoyl chloride, a sulfanilamide derivative, which was reacted with aroylhydrazides, amines, or thiols. A library of derivatives incorporating aroylhydrazone, [1,2,4]triazolo[3,4-b][1,3,4]thiadiazinyl- or 2-(cyanophenyl-methylene)-1,3,4-thiadiazol-3(2H)-yl moieties was thus synthesized. The new compounds were investigated as inhibitors of four α-carbonic anhydrases (CAs, EC 4.2.1.1), the human (h) isoforms hCA I and II, and the bacterial ones recently isolated from the extremophilic bacteria Sulfurihydrogenibium yellostonense (SspCA) and Sulfurihydrogenibium azorense (SazCA). Low nanomolar activity was observed against hCA II (KIs of 0.56-17.1 nM) whereas hCA I was less inhibited by these compounds (K(I)s of 86.4 nM-32.8 μM). The bacterial CAs were also effectively inhibited by these derivatives (K(I)s in the range of 0.77-234 nM against SazCA, and of 6.2-89.1 against SspCA, respectively), with several low nanomolar/subnanomolar inhibitors detected against both of them. As SspCA and SazCA are among the most thermostable and catalytically active CAs, it is of interest to find modulators of their activity for potential biotechnologic ...Continue Reading

References

Jan 3, 2008·Nature Reviews. Drug Discovery·Claudiu T Supuran
Jun 10, 2008·Expert Opinion on Emerging Drugs·Claudiu T SupuranGiuseppina De Simone
Apr 4, 2012·Journal of Enzyme Inhibition and Medicinal Chemistry·Claudiu T Supuran
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
Mar 16, 2013·Expert Opinion on Therapeutic Patents·Fabrizio Carta, Claudiu T Supuran
Apr 24, 2013·Expert Opinion on Therapeutic Patents·Andrea ScozzafavaFabrizio Carta
May 1, 2013·Expert Opinion on Drug Discovery·Giuseppina De SimoneClaudiu T Supuran
May 23, 2013·Acta Crystallographica. Section D, Biological Crystallography·Anna Di FioreGiuseppina De Simone

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Citations

Dec 17, 2014·Expert Opinion on Therapeutic Targets·Claudiu T Supuran, Clemente Capasso
Nov 20, 2014·Journal of Enzyme Inhibition and Medicinal Chemistry·Ahmed M AlafeefyClemente Capasso
Jul 10, 2014·Journal of Enzyme Inhibition and Medicinal Chemistry·Viviana De LucaClemente Capasso
Oct 3, 2015·Acta Pharmaceutica : a Quarterly Journal of Croatian Pharmaceutical Society and Slovenian Pharmaceutical Society, Dealing with All Branches of Pharmacy and Allied Sciences·Mostafa M Ghorab, Mansour S Alsaid
Apr 29, 2014·Journal of Enzyme Inhibition and Medicinal Chemistry·Clemente Capasso, Claudiu T Supuran
Mar 9, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Daniela VulloClemente Capasso
Feb 11, 2014·Bioorganic & Medicinal Chemistry Letters·Amrita K SalujaClaudiu T Supuran
May 13, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Rosa PerfettoClemente Capasso
Jul 6, 2018·Expert Opinion on Therapeutic Patents·Claudiu T Supuran, Clemente Capasso
Aug 10, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Sonia Del PreteClemente Capasso
Aug 4, 2015·Expert Opinion on Therapeutic Targets·Clemente Capasso, Claudiu T Supuran

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