In silico molecular modeling studies were carried out on some newly synthesized flavanoid analogues. Search for potential targets for these compounds was performed using pharmacophore-mapping algorithm employing inverse screening of some representative compounds to a large set of pharmacophore models constructed from human target proteins. Further, molecular docking studies were carried out to assess binding affinity of these compounds to proteins mediating tumor growth. In vitro anticancer studies were carried out on colon cancer cell lines (HCT116) to assess validity of this approach for target identification of the new compounds. Further important structural features of compounds for anticolon cancer activity were assessed using Monte Carlo-based SMILES and hydrogen graph-Based QSAR studies. In conclusion this study have depicted successful and stepwise application of pharmacophore mapping, molecular docking, and QSAR studies in target identification and lead optimization of flavonoids.

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In the racemic title compound, C16H14O3, the ring of the 4-hy­droxy­benzyl substituent group forms a dihedral angle of 80.12 (12)° with the benzene ring of the chromanone system. Two C atoms of the pyran­one ring and the H atoms on the benzyl α-C atom are disordered over two sites, with site-occupation factors of 0.818 (8) and 0.182 (8). The crystal structure is stabilized by O—H⋯O hydrogen bonds, which form parallel one-dimensional zigzag chains down the c axis and are inter­connected by both methine C—H⋯O hydrogen bonds and weak aromatic C—H⋯π inter­actions, giving a sheet structure lying parallel to [011].

Key indicators: single-crystal X-ray study; T = 295 K; mean (C-C) = 0.003 Å; R factor = 0.045; wR factor = 0.142; data-to-parameter ratio = 13.9.In the title compound, C 18 H 18 O 4 , the six-membered chroman-4-one ring adopts an envelope conformation with the C atom bonded to the bridging CH 2 atom as the flap. The dihedral angle between the mean plane of the fused pyranone ring and the dimethoxy-substituted benzene ring is 89.72 (2) . In the crystal, adjacent molecules are linked via C-HÁ Á Á interactions. Related literatureFor the biological activity and pharmaceutical properties of chromenes(benzopyrans) and a similar structure, see: Jasinski et al.

Objective: The objective of this study was to synthesize 7-amino-2-styrylchromone derivatives and evaluate their in vitro cytotoxic and antioxidant potential.Methods: 7-amino-2-styrylchromones were synthesized from 7-amino-2-methylchromone by condensing it with various substituted aromatic aldehydes. The cytotoxicity of the synthesized molecules was assessed against two cell lines, MCF-7 and HCT-116 by 3-(4,5-dimethyl thiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay. Cell cycle analysis of the most potent molecule ASC-7 was carried out. The antioxidant studies were conducted by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and nitric oxide methods.Result: (E)-7-amino-2-(3,4-methylenedioxystyryl)-4H-chromen-4-one (ASC-7) with inhibitory concentration 50% (IC 50 ) 56.0 µM was found to be the most potent molecule against MCF-7. ASC-7 induced G 0 /G 1 phase arrest of MCF-7. Furthermore, (E)-7-amino-2-(3,4-methylenedioxystyryl)-4H-chromen-4-one(ASC-7) showed good DPPH scavenging activity (IC 50 54.6 µM). However, none of the tested compounds exhibited nitric oxide scavenging property. Conclusion:This study reports the synthesis of 7-amino-2-styrylchromones. Some of the synthesized compounds showed moderate cytotoxicity against the tested cell lines MCF-7 and HCT-116. (E)-7-amino-2-(3,4-methylenedioxystyryl)-4H-chromen-4-one (ASC-7) was found to be the best cytotoxic and antioxidant agent.