Synthesis and antioxidant properties of substituted 3-benzylidene-7-alkoxychroman-4-ones

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

“…These findings were consistent with the previous reports that showed compound 13 20) and 18 21) had a strong DPPH radical scavenging activity. The catechol group in the B-ring of 3-benzylidene-4-chromanones is known to be an important structural feature for antioxidant activity.…”

“…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.…”

Quantitative Structure-cytotoxicity Relationship of 3-Benzylidenechromanones

“…It is urgent to explore the method by which this type of side-effect can be alleviated. We also found that the introduction of dimethylamino groups [6,12] and chloride [8] in the 4'-position of benzene ring produced comparable TS values with [3,10,15]. This indicates that molecular shape, size and polarization are useful for the evaluation of tumor-specificity of 3-benzylidenechromanone derivatives.…”

“…(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.…”