Crystal structure of 3-amino-8-methoxy-1-phenyl-1H-benzo[f]chromene-2-carbonitrile, C21H16N2O2

Okasha, Rawda M.; Amr, Abd El‐Galil E.; El‐Agrody, Ahmed M.; Al-Omar, Mohamed A.; Ghabbour, Hazem A.

doi:10.1515/ncrs-2016-0338

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“…Some 3-amino-1aryl-1H-benzo[f]chromene-2-carbonitrile derivatives exhibit c-Src kinase inhibitory and antiproliferative activities [22] and show a high potency for the inhibition of hAChE [23], while inducing cell cycle arrest and apoptosis in human cancer cells via dual inhibition of topoisomerase I and II [26,27]. In continuation of our previous work in benzochromenes chemistry [2][3][4]22,26,27] and the study of crystal structure for benzochromene derivatives [2,[28][29][30][31][32][33][34], we report the synthesis, NMR spectra, crystal structure, theoretical calculations (DFT), molecular modeling analyses, and cytotoxic activity of 3-amino-1-(2,5-dichlorophenyl)-8-1H-benzo[f]chromene-2-carbonitrile.…”

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confidence: 85%

Synthesis, Cytotoxic Activity, Crystal Structure, DFT Studies and Molecular Docking of 3-Amino-1-(2,5-dichlorophenyl)-8-methoxy-1H-benzo[f]chromene-2-carbonitrile

et al. 2021

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The target compound 3-amino-1-(2,5-d ichlorophenyl)-8-methoxy-1H-benzo[f]- chromene-2-carbonitrile (4) was synthesized via a reaction of 6-methoxynaphthalen-2-ol (1), 2,5-dichlorobenzaldehyde (2), and malononitrile (3) in ethanolic piperidine solution under microwave irradiation. The newly synthesized β-enaminonitrile was characterized by FT-IR, 1H NMR, 13C NMR, mass spectroscopy, elemental analysis and X-ray diffraction data. Its cytotoxic activity was evaluated against three different human cancer cell lines MDA-MB-231, A549, and MIA PaCa-2 in comparison to the positive controls etoposide and camptothecin employing the XTT cell viability assay. The analysis of the Hirshfeld surface was utilized to visualize the reliability of the crystal package. The obtained results confirmed that the tested molecule revealed promising cytotoxic activities against the three cancer cell lines. Furthermore, theoretical calculations (DFT) were carried out with the Becke3-Lee-Yang-parr (B3LYP) level using 6-311++G(d,p) basis. The optimization geometry for molecular structures was in agreement with the X-ray structure data. The HOMO-LUMO energy gap of the studied system was discussed. The intermolecular-interactions were studied through analysis of the topological-electron-density(r) using the QTAIM and NCI methods. The novel compound exhibited favorable ADMET properties and its molecular modeling analysis showed strong interaction with DNA methyltransferase 1.

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