Synthesis of new benzo[f]chromene-based heterocycles targeting anti-proliferative activity
Abu El-Azm, Fatma; El-Shahawi, Manal M.; Elgubbi, Amna S.; H. M. F. Madkour;
Abstract
Abstract: In this article β-enaminonitrile 1 undergoes intramolecular cyclocondensation reaction under acidic conditions to generate novel chromeno[2,3-b]azet-9-one derivative 2 in good yield. Ring expansion of the four membered ring of the azet-2(1H)-one derivative 2 to six and/or seven membered rings was achieved via reaction of compound 2 with different nitrogen nucleophiles. A new series of benzochromeneone, benzochromenopyrimidine, and benzo[f]coumarin derivatives were prepared via reaction of β-enaminonitrile 1 with different C-electrophiles. The structures of the products have been affirmed on the basis of analytical and spectral data. The anti-proliferative activity of the newly synthesized compounds against two human epithelial cell lines; liver (HepG2) and breast (MCF-7) in addition to normal fibroblasts (WI-38) was investigated. Derivatives 4 and 10 had significant and selective anti-proliferative activity against liver and breast cancer cell lines without harming normal fibroblasts. Graphic abstract: [Figure not available: see fulltext.].
Other data
Title | Synthesis of new benzo[f]chromene-based heterocycles targeting anti-proliferative activity | Authors | Abu El-Azm, Fatma ; El-Shahawi, Manal M.; Elgubbi, Amna S.; H. M. F. Madkour | Keywords | Anti-proliferative activity;Benzo[f]chromene;Benzo[f]chromeneone;Benzo[f]chromeno[2,3-d]pyrimidines;Benzo[f]coumarin;Chromeno[2,3-b]azet-9-one;Intramolecular cyclocondensation | Issue Date | 1-May-2021 | Publisher | SPRINGER | Journal | Journal of the Iranian Chemical Society | Volume | 18 | Start page | 1081 | End page | 1092 | ISSN | 1735-207X | DOI | 10.1007/s13738-020-02092-w | Scopus ID | 2-s2.0-85094140696 | Web of science ID | WOS:000584922600001 |
Attached Files
File | Description | Size | Format | |
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AbuEl-Azm2020_Article_SynthesisOFNewBenzo[F]chromene.pdf | 1.47 MB | Unknown | View/Open |
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