Microwave-assisted synthesis of dihydropyridones from curcumin

Crystal Structure of 2-(4-Hydroxy-3-Methoxyphenyl)-6- (4-Hydroxy-3-Methoxystyryl)-1-Methyl-2, 3-Dihydropyridine-4 (1H)-One by X-Ray Powder Diffraction

“…The torsion angels between geminal protons H39 and H40 and the proton H38 are 40.1 and -81.9°. This supports the assignment of the two peaks that appear in 1 H NMR spectrum of the studied compound which appear as two doublets of doublets at 2.42 ppm (J = 16 and 4 Hz) and at 2.84 ppm (J = 16 and 7 Hz) (Elias et al, 2008). The distortion of the pyridone ring forces the protons H39 and H40 to adopt two different torsion angles with the O18 atom.…”

“…The compound was synthesized according to previously described procedure (Elias et al, 2008). High resolution x-ray powder diffraction data was collected on an MXPI8A-HF (MAC science, Japan) diffractometer with Cu-Kα (1.540593 Å) radiation at room temperature.…”

“…Sugiyama et al (1970) were synthesized the dihydropyridone 2, 3-dihydro-1, 2-diphenyl-6-(2-phenylethenyl)-4-pyridone from the reaction of 6-methyl-1, 2-diphenyl-2, 3-dihydro-4-pyridone with benzaldehyde. In a previous study (Elias et al, 2008) we reported the synthesis of a series of dihydropyridones that structurally related to that synthesized by Sugiyama et al (1970), by the reaction of curcumin and amines or amine acetates under microwave irradiation in an approach that seems unexpected.…”

Antiviral and Quantitative Structure Activity Relationship Study for Dihydropyridones Derived from Curcumin

“…The screened dihydropyridones were synthesized via previously described method (Elias et al, 2008). These compounds as well as curcumin were evaluated for preliminary estimation of the in vitro tumor inhibiting activity against a variety of viruses included: HIV-1, Bovin Viral Diarrhea (BVDV), Yellow Fever (YFV), Reovirus 1 (Reo), Herpesvirus 1 (HSV-1), Vaccinia VV), Vescular Stomatitis (VSV), Coxackie virus B2 CVB-2), Poliovirus 1 (Sb-1) and Respiratory Syncytial (RSV) viruses, using microculture assay (MTT) method (Tang et al, 2010).…”

“…Dihydropyridones are important intermediates for the synthesis of natural products, particularly alkaloids (Dong et al, 2005;Comins and Ollinger, 2001;Elias et al, 2008) and they have been extensively investigated as valuable building block for the construction of piperidines, perhydroquinolens, indolizidines, quinolizidines and other alkaloid systems, with a wide range of a biological and pharmacological activities. These compounds are known for their antiproliferative and antitubolin activities (Magedov et al, 2008) and as potential selective inhibitors of receptor tyrosine kinase (Hu et al, 2008;Goodman et al, 2007).…”