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Synthesis, Characterization, and Cytotoxicity Evaluation of Some New Benzo[ f ]coumarin Derivatives
Author(s) -
Mohamed Khaled S.,
Elbialy Engy E.
Publication year - 2018
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3115
Subject(s) - chemistry , coumarin , salicylaldehyde , benzaldehyde , cytotoxicity , condensation reaction , medicinal chemistry , aryl , stereochemistry , organic chemistry , in vitro , schiff base , catalysis , biochemistry , alkyl
Interaction of 2‐(bromoacetyl)‐3 H ‐benzo[ f ]coumarin ( 1 ) with salicylaldehyde afforded 2‐(2‐oxo‐2‐(3 H ‐benzo[ f ]coumarin‐2‐yl)ethoxy)benzaldehyde ( 2 ) which underwent self‐condensation in refluxing dimethylformamide (DMF) to afford 2‐(2‐benzofuroyl)‐3 H ‐benzo[ f ]coumarin (3). Treatment of 1 with o‐ aminothiophenol ( 4 ) gave 2‐(2‐((2‐aminophenyl)thio)acetyl)‐3 H ‐benzo[ f ]coumarin (5) . Refluxing of 5 in DMF led to formation of 2‐(4 H ‐[1,4]‐benzothiazin‐3‐yl)‐3 H ‐benzo[ f ]coumarin (6). Treatment of 1 with aryl amines 7a–d in boiling DMF gave 1‐aryl‐3‐hydroxybenzo[5,6]chromeno[4,3‐ b ]pyrrol‐4(1 H )‐one ( 10a–d ) . Condensation of 11 with o ‐phenylenediamine gave 2‐(2‐methyl‐2,3‐dihydro‐1 H ‐benzimidazol‐2‐yl)‐3 H ‐benzo[ f ]coumarin ( 12 ). Interaction of 2‐acetyl‐3 H ‐benzo[ f ]coumarin ( 11 ) with arylidene malonononitrile gave 4‐hydroxy‐2‐(3 H ‐benzo[ f ]coumarin‐2‐yl)‐5 H ‐dibenzo[ c , f ]chromen‐5‐one ( 16) . All reaction products were characterized by analytical and spectral data. Novel compounds bioactivity as antitumor were examined for in vitro cytotoxicity against HepG‐2 and MCF‐7.