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- Title
DESIGN, SYNTHESIS, AND CYTOTOXIC ACTIVITY OF SOME NOVEL N-(SUBSTITUTED) BENZAMIDE DERIVATIVES BEARING COUMARIN AND 1-AZOCOUMARIN COMPOUNDS.
- Authors
Al-Hazmi, Ghaferah H.
- Abstract
Among oxygen-containing heterocyclic compounds such as coumarin and azacoumarin derivatives, the scaffold has become an important construction motif for developing new drugs. Coumarin and its derivatives possess many types of biological activities and have been reported to show significant cytotoxic activity. N-(6,8-disubstituted coumarin-3-yl)benzamides (8a-c) namely (3-N-(benzoyl) aminocoumarin-6-ylmethyl acetate (8a); N-[6-(1-acetylpyrazol-3-yldiazineyl) coumarin-3-yl] benzamide (8b); N-(8-methoxy-6-bromo-coumarin-3-yl) benzamide (8c), were synthesized via a cyclocondensation reaction of 5-(chloromethyl)-2-hydroxybenzaldehyde (3), 5-(pyrazol-3-yl-diazineyl)-2-hydroxybenzaldehyde (4), and 5-bromo-3-methoxy-2-hydroxybenzaldehyde (5) with N-benzoylglycine (7), in good yield. Treatment of compound 8c with ammonia in the presence of anhydrous potassium carbonate to yield N-(5-bromo-8-methoxy-1-azocoumarin-3-yl) benzamide (9). Compound (9) was acetylated with acetic anhydride to give N-(2-acetoxy-5-bromo-8-methoxyquinolin-3-yl) benzamide (10). N-(substituted coumarin and azacoumarin-3-yl) benzamides (8-10) were tested for their in vitro cytotoxic activity against (HepG2) cell line. Furthermore, DNA flow cytometry investigation over HepG2 cells indicated that compound 8a demonstrated arrest at G1/S stages of the cell cycle and induction of apoptosis by rising pre-G1 stage. Compound 8a displayed a significant tubulin polymerization inhibition.
- Subjects
COUMARINS; COUMARIN derivatives; BENZAMIDE; ACETATES; POTASSIUM carbonate; ACETIC anhydride; AMMONIA compounds; AMMONIA
- Publication
Bulletin of the Chemical Society of Ethiopia, 2023, Vol 37, Issue 4, p1003
- ISSN
1011-3924
- Publication type
Article
- DOI
10.4314/bcse.v37i4.16