Synthesis, stereochemical assignments, and biological activities of homoisoflavonoids

Quantitative Structure-cytotoxicity Relationship of 3-Benzylidenechromanones

“…Compound [16] showed antibacterial and antifungal activities (33). Compounds [9,11] inhibited the efflux of antimicrobials, such as ethidium bromide from the Mycobacterium smegmatis mc 2 155, suggesting their possible candidacy as anti-tuberculosis drugs by reducing drug-resistance (10). On the other hand, the anti-cancer study of homoisoflavonoids has been limited, possibly due to the absence of appropriate assay method for tumor-selectivity.…”

“…(3E)-2,3-Dihydro-3-(phenylmethylene)-4H-1-benzopyran-4-one [1], (3E)-2,3-dihydro-3-[(4-hydroxyphenyl) methylene]-4H-1-benzopyran-4-one [2], (3E)-2,3-dihydro-3-[(3,4-dihydroxyphenyl)methylene]-4H-1-benzopyran-4-one [3], (3E)-2,3-dihydro-3-[(4-methoxyphenyl)methylene]-4H-1-benzopyran-4-one [4], (3E)-2,3-dihydro-3-[(3,4-dimethoxyphenyl)methylene]-4H-1-benzopyran-4-one [5], (3E)-2,3-dihydro-3-[(4-dimethylaminophenyl)methylene]-4H-1-benzopyran-4-one [6], (3E)-2,3-dihydro-3-[(4-fluorophenyl)methylene]-4H-1-benzopyran-4-one [7], (3E)-3-[(4-chlorophenyl)methylene]-2,3-dihydro-4H-1-benzopyran-4-one [8], (3E)-2,3-dihydro-7-hydroxy-3-[(4-hydroxyphenyl)methylene]-4H-1-benzopyran-4-one [9], (3E)-2,3-dihydro-3-[(3,4-dihydroxyphenyl)methylene]-7-hydroxy-4H-1-benzopyran-4-one [10], (3E)-2,3-dihydro-7-hydroxy-3-[(4-methoxyphenyl)methylene]-4H-1-benzopyran-4-one [11], (3E)-2,3-dihydro-3-[(4-dimethylaminophenyl)methylene]-7-hydroxy-4H-1-benzopyran-4-one [12], (3E)-2,3-dihydro-7-methoxy-3-(phenylmethylene)-4H-1-benzopyran-4-one [13], (3E)-2,3-dihydro-3-[(4-hydroxyphenyl)methylene]-7-methoxy-4H-1-benzopyran-4-one [14], (3E)-2,3-dihydro-3-[(3,4-dihydroxyphenyl)methylene]-7-methoxy-4H-1-benzopyran-4-one [15], (3E)-2,3-dihydro-7-methoxy-3-[(4-methoxyphenyl)methylene]-4H-1-benzopyran-4-one [16] and (3E)-2,3-dihydro-3-[(4-dimethylaminophenyl)methylene]-7-methoxy-4H-1-benzopyran-4-one [17] (structures shown in Figure 1) were synthesized by base-catalyzed condensation of appropriate 4-chromanone with substituted benzaldehyde derivatives according to previous methods (19,20). All compounds were dissolved in DMSO at 40 mM and stored at -20˚C before use.…”

Synthesis and Biological Evaluation of 3-Benzylidene-4-chromanone Derivatives as Free Radical Scavengers and α-Glucosidase Inhibitors

“…Compound 1a was commercially available and compounds 1b and c were synthesized from resorcinol according to the procedure of Foroumadi et al 21) With 1a-c in hand, each was condensed with benzaldehyde derivatives (2a-h) in the presence of piperidine to provide the 3-benzylidene-4-chromanone derivatives (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20).…”

“…[10][11][12][13][14] Several natural and synthetic 3-benzylidene-4-chromanones are related structurally to flavonoids and were found to possess various biological properties such as antioxidant, antifungal, antiviral, anti-mutagenic, antiproliferative, anti-allergic, antihistaminic, anti-inflammatory, and monoamine oxidase inhibitory activity. [15][16][17][18][19][20][21][22][23][24] However, no systematically evaluated data are available on the inhibitory activity of α-glucosidase by 3-benzylidene-4-chromanone derivatives. 14) In order to further explore new biological activities of this family of compounds, we synthesized a series of 3-benzylidene-4-chromanone derivatives and investigated the structure-activity relationships (SAR) of these 3-benzylidene-4-chromanone derivatives to inhibit α-glucosidase and exhibit antioxidant activity.…”

New efficient synthesis and bioactivity of homoisoflavonoids

“…In our research program, we are interested in synthesis and bioactivity evaluation of homoisoflavonoids 5,6 and an increasing demand for a short and efficient method prompted us to develop a simple and general method for the synthesis homoisoflavones.…”