The Crystal Structure of 2-Amino-4-(2,3-Dichlorophenyl)-6-Methoxy-4<i>H</i>-Benzo[<i>h</i>]chromene-3-Carbonitrile: Antitumor and Tyrosine Kinase Receptor Inhibition Mechanism Studies

The target compound, 2-amino-4-(2,3-dichlorophenyl)-6-methoxy-4<i>H</i>-benzo[<i>h</i>]chromene -3-carbonitrile <b>(4)</b>, was synthesized via the reaction of 4-methoxynaphthalen-1-ol <b>(1)</b>, 2,3-dichlorobenzaldehyde <b>(2)</b>, and ma...

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Bibliographic Details
Main Authors: Ahmed M. El-Agrody, Ahmed M. Fouda, Hany M. Mohamed, Mohammed Y. Alshahrani, Hazem A. Ghabbour, Abd El-Galil E. Amr, Rawda M. Okasha, Ahmed M. Naglah, Abdulrahman A. Almehizia, Ahmed A. Elhenawy
Format: Article
Language:English
Published: MDPI AG 2022-05-01
Series:Crystals
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Online Access:https://www.mdpi.com/2073-4352/12/5/737
Description
Summary:The target compound, 2-amino-4-(2,3-dichlorophenyl)-6-methoxy-4<i>H</i>-benzo[<i>h</i>]chromene -3-carbonitrile <b>(4)</b>, was synthesized via the reaction of 4-methoxynaphthalen-1-ol <b>(1)</b>, 2,3-dichlorobenzaldehyde <b>(2)</b>, and malononitrile <b>(3)</b> in an ethanolic piperidine solution under microwave irradiation. The synthesized <i>β</i>-enaminonitrile derivative <b>(4)</b> was characterized by spectral data and X-ray diffraction. The in vitro anti-proliferative profile was conducted against five cancer cell lines and was assessed for compound <b>4</b>, which revealed strong and selective cytotoxic potency. This derivative showed promising inhibition efficacy against the EGFR and VEGFR-2 kinases in comparison to Sorafenib as a reference inhibitor. Lastly, the docking analysis into the EGFR and VEGFR-2 active sites was performed to clarify our biological findings.
ISSN:2073-4352