Synthesis and Biological Evaluation of Coumarin-Linked 4-Anilinomethyl-1,2,3-Triazoles as Potent Inhibitors of Carbonic Anhydrases IX and XIII Involved in Tumorigenesis

A series of coumarin-linked 4-anilinomethyl-1,2,3-triazoles ( - ) was synthesized via a molecular hybridization approach, through carbon C-6 of the coumarin moiety. The synthesized compounds were evaluated for their inhibition of carbonic anhydrase (CA) isoforms I, II, IX and XIII. CAs IX and XIII w...

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Published inMetabolites Vol. 11; no. 4; p. 225
Main Authors Thacker, Pavitra S, Tiwari, Prerna L, Angeli, Andrea, Srikanth, Danaboina, Swain, Baijayantimala, Arifuddin, Mohammed, Supuran, Claudiu T
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 07.04.2021
MDPI
Subjects
1,2,3-triazole
Acidosis
Carbonic anhydrase II
carbonic anhydrases
Chromatography
Coumarin
hCA IX
hCA XIII
Hybridization
Hypoxia
Isoforms
Metabolism
Metabolites
Metastasis
Triazoles
Tumorigenesis
Tumors
carbonic anhydrases
hCA XIII
1,2,3-triazole
coumarin
hCA IX
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Summary:A series of coumarin-linked 4-anilinomethyl-1,2,3-triazoles ( - ) was synthesized via a molecular hybridization approach, through carbon C-6 of the coumarin moiety. The synthesized compounds were evaluated for their inhibition of carbonic anhydrase (CA) isoforms I, II, IX and XIII. CAs IX and XIII were selectively inhibited over the off-target isoforms I and II. The best inhibitory profiles against CA IX were shown by compounds , and (K < 50 nM), with compound displaying the best inhibition with a K value of 36.3 nM. Compounds , , , and exhibited the best inhibitory profiles against CA XIII (K < 100 nM). These compounds can be further explored for the discovery of potent and effective CA IX and CA XIII inhibitors.
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ISSN:2218-1989
2218-1989
DOI:10.3390/metabo11040225