Journal
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
Volume 37, Issue 1, Pages 994-1004Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1080/14756366.2022.2055553
Keywords
Quinazoline-benzenesulfonamide hybrids; Suzuki coupling; Carbonic anhydrase inhibitors; Molecular docking
Funding
- National Research Foundation of Korea (NRF) - Korean government (MSIT) [2018R1A5A2023127]
- BK21 FOUR program - Ministry of Education of Korea through NRF
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In this study, a series of 4-anilinoquinazoline-based benzenesulfonamides were designed and synthesized as potential carbonic anhydrase inhibitors (hCAIs). These compounds showed high inhibitory activity and have potential applications in the treatment of epilepsy, glaucoma, and cancer.
Human carbonic anhydrase inhibitors (hCAIs) are a key therapeutic class with a multitude of novel applications such as anticonvulsants, topically acting antiglaucoma, and anticancer drugs. Herein, a new series of 4-anilinoquinazoline-based benzenesulfonamides were designed, synthesised, and biologically assessed as potential hCAIs. The target compounds are based on the well-tolerated kinase scaffold (4-anilinoquinazoline). Compounds 3a (89.4 nM), 4e (91.2 nM), and 4f (60.9 nM) exhibited 2.8, 2.7, and 4 folds higher potency against hCA I when compared to the standard (AAZ, V), respectively. A single digit nanomolar activity was elicited by compounds 3a (8.7 nM), 4a (2.4 nM), and 4e (4.6 nM) with 1.4, 5, and 2.6 folds of potency compared to AAZ (12.1 nM) against isoform hCA II, respectively. Structure-activity relationship (SAR) and molecular docking studies validated our design approach that revealed highly potent hCAIs.
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