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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MDPI AG
2022-05-01
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| author | 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 |
| author_facet | 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 |
| author_sort | Ahmed M. El-Agrody |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-10T03:04:55Z |
| format | Article |
| id | doaj.art-83582327bd1d4d0182428e905a475830 |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-03-10T03:04:55Z |
| publishDate | 2022-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-83582327bd1d4d0182428e905a4758302023-11-23T10:36:18ZengMDPI AGCrystals2073-43522022-05-0112573710.3390/cryst12050737The 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 StudiesAhmed M. El-Agrody0Ahmed M. Fouda1Hany M. Mohamed2Mohammed Y. Alshahrani3Hazem A. Ghabbour4Abd El-Galil E. Amr5Rawda M. Okasha6Ahmed M. Naglah7Abdulrahman A. Almehizia8Ahmed A. Elhenawy9Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo 11884, EgyptChemistry Department, Faculty of Science, King Khalid University, Abha 61413, Saudi ArabiaChemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo 11884, EgyptDepartment of Clinical Laboratory Science, College of Applied Medical Science, King Khalid University, Abha 61413, Saudi ArabiaDepartment of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, EgyptPharmaceutical Chemistry Department, Drug Exploration and Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi ArabiaChemistry Department, Faculty of Science, Taibah University, Medina 30002, Saudi ArabiaPharmaceutical Chemistry Department, Drug Exploration and Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi ArabiaPharmaceutical Chemistry Department, Drug Exploration and Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi ArabiaChemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo 11884, EgyptThe 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.https://www.mdpi.com/2073-4352/12/5/737benzochromenesantitumor activityEGFRVEGFR-2dockingX-ray |
| spellingShingle | 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 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 Crystals benzochromenes antitumor activity EGFR VEGFR-2 docking X-ray |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| topic | benzochromenes antitumor activity EGFR VEGFR-2 docking X-ray |
| url | https://www.mdpi.com/2073-4352/12/5/737 |
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