Abstract
A new compound (E)-3-[3-(4-morpholinophenyl)acryloyl]-2H-chromen-2-one, a coumarin based chalcone derivative, has been successfully synthesized employing a molecular hybridization method through the reaction between 3-acetylcoumarin and 4-morpholinobenzaldehyde using a Claisen–Schmidt reaction using pTSA as a catalyst. The structure of the title compound was established using spectroscopic data FTIR, HRESI-MS, 1H- and 13C-NMR. The anticancer activity against breast cancer cells line T47D and cervix cancer cells line HeLa was determined using an MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay.
Highlights
Combining different pharmacophoric moieties from different bioactive compounds to generate a new hybrid compound showing better affinity and efficacy, with fewer undesired side effects, than the parent compounds becomes a new concept in drug design and development, which is known as molecular hybridization [1]
Coumarins are secondary metabolites possessing a benzopyran ring that can be found as synthetic products and are already known for their various pharmacological activities such as antimycobacterial [2], inhibitor of HIV-1 [3], inhibitor of platelet aggregation, and to smooth muscle contraction in vitro [4]
Compounds of the ketocoumarin type are usually synthesized from salicylaldehyde using a cyclic
Summary
Combining different pharmacophoric moieties from different bioactive compounds to generate a new hybrid compound showing better affinity and efficacy, with fewer undesired side effects, than the parent compounds becomes a new concept in drug design and development, which is known as molecular hybridization [1]. An example of such hybridization is a compound constructed from coumarin and chalcones. The pharmacological activities of coumarin–chalcone derivatives containing urea moiety as an anticancer agent has been reported [11] Based on this consideration, we designed a coumarin–chalcone hybrid compound containing morpholino-phenyl moiety and synthesized it successfully through a Claisen–Schmidt reaction. The prepared compound was evaluated in relation to its anticancer activity against breast cancer cell line T47D and cervix cancer cell line HeLa using an MTT assay
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