- Green synthesis, antioxidant and antibacterial activities of 4-aryl-3,4-dihydropyrimidinones/thiones derivatives of curcumin. Theoretical calculations and mechanism study
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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.
- Khaldi-Khellafi, Nassima,Makhloufi-Chebli, Malika,Oukacha-Hikem, Djamila,Bouaziz, Souhila Terachet,Lamara, Kamilia Ould,Idir, Taous,Benazzouz-Touami, Amina,Dumas, Fran?oise
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p. 261 - 269
(2019/01/08)
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- Chitosan: An efficient biodegradable and recyclable green catalyst for one-pot synthesis of 3,4-dihydropyrimidinones of curcumin in aqueous media
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An efficient procedure for the synthesis of curcumin 3,4- dihydropyrimidinones has been developed by simple one-pot condensation of curcumin, aromatic aldehydes and urea/thiourea in the presence of commercially available chitosan in 2% acetic acid in aqueous media at 60°C for 80-90 min. In the reaction, curcumin: a potential biologically active molecule has been used as a component of multi-component synthesis using chitosan as an efficient biodegradable and recyclable green catalyst. The resultant product curcumin 3,4-dihydropyrimidinone is formed in excellent yield (97%). The chitosan catalyst can be reused for without loss of catalytic activity.
- Lal, Jaggi,Gupta, Sushil K.,Agarwal, Dau D.
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- Design, synthesis, synergistic antimicrobial activity and cytotoxicity of 4-aryl substituted 3,4-dihydropyrimidinones of curcumin
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3,4-Dihydropyrimidinones of curcumin were synthesized in excellent yield by multi-component one-pot condensation of curcumin, substituted aromatic aldehydes and urea/thiourea under solvent free conditions using SnCl 2·2H2O catalyst. All the synthesized compounds have been characterized by IR, 1H NMR, 13C NMR, Mass spectra as well as elemental analyses. The synthesized compounds 4a-n were evaluated for their synergistic antimicrobial (antibacterial and antifungal) activity against bacteria and fungi. Zone of inhibition was measured by adopting disc diffusion method. In vitro minimum inhibitory concentrations were measured using broth microdilution and food poisoning method. In addition to this in vitro cytotoxicity of synthesized compounds against three human cancer lines Hep-G2, HCT-116 and QG-56 were also evaluated. Most of the compounds showed interesting antimicrobial and cytotoxic activity as compared to curcumin, that is, the compounds derived from 2-hydroxy benzaldehyde, 4-hydroxy benzaldehyde and 4-hydroxy-3-methoxy benzaldehyde showed the highest biological activity as compared to other compounds.
- Lal, Jaggi,Gupta,Thavaselvam,Agarwal
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supporting information; experimental part
p. 2872 - 2876
(2012/06/01)
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