Synthesis, structure, and estrogenic activity of 2- and 3-substituted 2,3-dihydro-4H-1-benzopyran-4-ones

A short synthesis of 7-amino alkoxy homoisoflavonoides

“…The results show that best and more efficient condition to the synthesis of homoisoavonoids is provided by using HCl in ethanol at room temperature which leads to achieve the product with highest yield than others. [27][28][29][30][31][32][33][34] Based on the above, by this achievement, the scope of homoisoavonoids as very medicinally important compounds was developed. Rapid formation and easily purication of target products, needing a little of HCl (g) to accelerate reaction can be countered as other advantages of this protocol.…”

Quantitative Structure-cytotoxicity Relationship of 3-Benzylidenechromanones

“…(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

“…mp 110°C (lit. 111°C 22) ). 1H, ddd, J=8.3, 7.1, 1.7 Hz, H-7), 7.08 (1H, ddd, J=7.9, 7.1, 0.9 Hz, H-6), 6.97 (1H, dd, J=8.3, 0.9 Hz, H-8), 6.94 (1H, d, J=8.3 Hz, H-5′), 6.90 (1H, dd, J=8.3, 1.9 ).…”

“…[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.…”