1373886-16-8

Basic information

• Product Name: 5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-phenyl-3,4-dihydropyrimidin-2(1H)-thione
• Synonyms: 5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-phenyl-3,4-dihydropyrimidin-2(1H)-thione
• CAS NO: 1373886-16-8
• Molecular Weight: 514.602
• Mol File: 1373886-16-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-phenyl-3,4-dihydropyrimidin-2(1H)-thione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-phenyl-3,4-dihydropyrimidin-2(1H)-thione(1373886-16-8)
• EPA Substance Registry System: 5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-phenyl-3,4-dihydropyrimidin-2(1H)-thione(1373886-16-8)

Safety Data

• Hazardous Substances Data: 1373886-16-8(Hazardous Substances Data)

Upstream product

• 458-37-7 curcumin 
• 100-52-7 benzaldehyde 
• 17356-08-0 thiourea 

Relevant articles and documents

Design, structure activity relationship, cytotoxicity and evaluation of antioxidant activity of curcumin derivatives/analogues

New fourteen 3,4-dihydropyrimidine derivatives/analogues of curcumin (2a-2n) were designed, synthesized and biologically evaluated for their cytotoxicity and antioxidant activity. Cytotoxicity effect has been evaluated against three cell lines HeLa, HCT-116 and QG-56 by MTT assay method. From SAR study, it has been revealed that particularly, compound 2e and 2j (IC50 value 12.5 μM) have shown better cytotoxicity effect against three cell lines. According to results of SAR study, it was found that 3,4-dihydropyrimidines of curcumin, 2c, 2d, 2j and 2n exhibited better antioxidant activity than curcumin. A correlation of structure and activities relationship of these compounds with respect to drug score profiles and other physico-chemical properties of drugs are described and verified experimentally. Therefore, we conclude that physico-chemical analyses may prove structural features of curcumin analogues with their promising combined cytotoxicity/antioxidant activity and it is also concluded from virtual and practical screening that the compounds were varied to possess a broad range of lipophilic character, revealed by Log P values.

Design, synthesis, synergistic antimicrobial activity and cytotoxicity of 4-aryl substituted 3,4-dihydropyrimidinones of curcumin

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.