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Novel benzofuran-based sulphonamides as selective carbonic anhydrases IX and XII inhibitors: synthesis and in vitro biological evaluation.
- Source :
- Journal of Enzyme Inhibition & Medicinal Chemistry; Dec2020, Vol. 35 Issue 1, p298-305, 8p
- Publication Year :
- 2020
-
Abstract
- Pursuing on our efforts toward searching for efficient hCA IX and hCA XII inhibitors, herein we report the design and synthesis of new sets of benzofuran-based sulphonamides (4a,b, 5a,b, 9a–c, and 10a–d), featuring the zinc anchoring benzenesulfonamide moiety linked to a benzofuran tail via a hydrazine or hydrazide linker. All the target benzofurans were examined for their inhibitory activities toward isoforms hCA I, II, IX, and XII. The target tumour-associated hCA IX and XII isoforms were efficiently inhibited with K<subscript>I</subscript>s spanning in ranges 10.0–97.5 and 10.1–71.8 nM, respectively. Interestingly, arylsulfonehydrazones 9 displayed the best selectivity toward hCA IX and XII over hCA I (SIs: 39.4–250.3 and 26.0–149.9, respectively), and over hCA II (SIs: 19.6–57.1 and 13.0–34.2, respectively). Furthermore, the target benzofurans were assessed for their anti-proliferative activity, according to US-NCI protocol, toward a panel of sixty cancer cell lines. Only benzofurans 5b and 10b possessed selective and moderate growth inhibitory activity toward certain cancer cell lines. [ABSTRACT FROM AUTHOR]
- Subjects :
- BIOSYNTHESIS
SULFONAMIDES
BENZOFURANS
CELL lines
MOIETIES (Chemistry)
CANCER cells
Subjects
Details
- Language :
- English
- ISSN :
- 14756366
- Volume :
- 35
- Issue :
- 1
- Database :
- Complementary Index
- Journal :
- Journal of Enzyme Inhibition & Medicinal Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 147176713
- Full Text :
- https://doi.org/10.1080/14756366.2019.1697250