Green synthesis, antioxidant and antibacterial activities of 4-aryl-3,4-dihydropyrimidinones/thiones derivatives of curcumin. Theoretical calculations and mechanism study

3,4-Dihydropyrimidin-2(1H)-one/thione analogs of curcumin were synthesized in good yield by a one-pot multi-component cyclocondensation using curcumin, substituted aromatic aldehydes, and urea/thiourea in less volume of ethanol catalysed by commercial heteropolyacide Keggin type H3PMo12O40 5% mol as...

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Bibliographic Details
Published in:	Journal of molecular structure Vol. 1181; pp. 261 - 269
Main Authors:	Khaldi-Khellafi, Nassima, Makhloufi-Chebli, Malika, Oukacha-Hikem, Djamila, Bouaziz, Souhila Terachet, Lamara, Kamilia Ould, Idir, Taous, Benazzouz-Touami, Amina, Dumas, Françoise
Format:	Journal Article
Language:	English
Published:	Elsevier B.V 05-04-2019
Subjects:	Antibacterial activity Antioxidant capacity Curcumin-dihydropyrimidinones/thiones Microwave irradiation Nitrogen heterocycles Theoretical studies Microwave irradiation Antioxidant capacity Curcumin-dihydropyrimidinones/thiones Antibacterial activity Nitrogen heterocycles Theoretical studies
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Summary:	3,4-Dihydropyrimidin-2(1H)-one/thione analogs of curcumin were synthesized in good yield by a one-pot multi-component cyclocondensation using curcumin, substituted aromatic aldehydes, and urea/thiourea in less volume of ethanol catalysed by commercial heteropolyacide Keggin type H3PMo12O40 5% mol as a recyclable and nontoxic catalyst under conventional heating and microwave irradiation. All the synthesized curcumin derivatives 4a–n were screened for antioxidant and antimicrobial activity. Biological activity data of the synthesized showed that most of the synthesized compounds exhibited greater antioxidant and antibacterial activity than curcumin. Geometries of synthesized compounds were optimized by using B3LYP method with 6-31G* basis set. Then, DFT based reactivity descriptors such as HOMO, LUMO, chemical hardness, electronegativity, chemical potential were calculated and discussed. An efficient green synthesis of 3,4-Dihydropyrimidin-2(1H)-one/thione analogs of curcumin was developed involving a one-pot multi-component cyclocondensation of curcumin using substituted aromatic aldehydes and urea/thiourea catalysed by commercial heteropolyacid Keggin type H3PMo12O40 catalyst under conventional heating and microwave irradiation. The derivatives were screened for antioxidant and antimicrobial activity. [Display omitted] •H3PMo12O40 as green catalyst in the synthesis of 4-aryl-3,4-dihydropyrimidinones/thiones of curcumin.•Conventional heating and microwave irradiation.•Theoretical calculations and mechanism studies.•Antioxidant and antibacterial activity are greater than curcumin.•Geometries of synthesized compounds were optimized by using B3LYP method with 6-31G* basis set.
ISSN:	0022-2860 1872-8014
DOI:	10.1016/j.molstruc.2018.12.104