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Synthesis of novel coumarin and benzocoumarin derivatives and their biological and photophysical studies
Author(s) -
AbdElAziz Alaa S.,
Mohamed Hany M.,
Mohammed Shawkat,
Zahid Shamsulhaq,
Ata Athar,
Bedair Ahmed H.,
ElAgrody Ahmed M.,
Harvey Pierre D.
Publication year - 2007
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.5570440610
Subject(s) - chemistry , coumarin , nucleophile , ring (chemistry) , methylene , fluorescence , proton nmr , medicinal chemistry , nucleophilic substitution , stereochemistry , organic chemistry , catalysis , physics , quantum mechanics
everal derivatives of coumarin‐3 N ‐carboxamides ( 3‐21 ) have been prepared via the reaction of the coumarin‐3‐carbonyl chloride ( 1 ) with a number of nucleophiles. Novel double‐headed coumarin‐3 N ‐carboxamides ( 26‐33 ) were also produced using the same method. The Pechmann‐Duisberg reaction was applied to prepare new benzo[ f ]‐ benzo[ h ]coumarins and 4‐(chloromethyl)‐pyrano[3,2‐ c ]coumarin‐2‐one ( 36‐42 ). The reaction of 1‐chloromethylbenzo[ f ]coumarins ( 36 ) with cyanide anion under different reaction conditions was also investigated in order to assess its suitability for nucleophilic substitution reactions as well as ring transformation products ( 43‐49 ). Synthesis of 1‐((benzo[ d ]thiazol‐2‐yl)methyl)‐9‐hydroxybenzo[ f ]coumarin ( 50 ) represented the first example of methylene bridge‐head heterocyclecontaining benzo[ f ]coumarin. Some of the newly prepared coumarins exhibited anti‐bacterial activity against Gram Positive and Gram negative bacteria. Compound 36d was found to be active against all the screened bacteria. Photophysical studies were performed on selected fluorescent benzo[ f ]‐ and benzo[ h ]coumarin and the quantum yields were also calculated. All new compounds were characterized by IR, MS, 1 H and 13 C NMR, as well as elemental analysis.