4-Aryl-4H-naphthopyrans derivatives: One-pot synthesis, evaluation of Src kinase inhibitory and anti-proliferative activities

Ali Rafinejad, Asal Fallah-Tafti, Rakesh Tiwari, Amir Nasrolahi Shirazi, Deendayal Mandal, Abbas Shafiee, Keykavous Parang, Alireza Foroumadi, Tahmineh Akbarzadeh

Research output: Contribution to journalArticle

Abstract

Background: A series of 2-Amino-4-Aryl-4H-benzo[h or f]chromene-3- carbonitrile derivatives were synthesized and evaluated for inhibition of Src kinase and cell proliferation in breast carcinoma (BT-20) cell lines. Methods: The one-pot, three-component reaction of α or β-naphthol, malonitrile and an aromatic aldehyde in the presence of diammonium hydrogen phosphate was afforded the corresponding 2-Amino-4-Aryl-4H-benzo[h or f] chromene-3- carbonitrile derivatives, All target compounds were evaluated for inhibition of Src kinase and cell proliferation in breast carcinoma (BT-20) cell lines. Results: Among all tested compounds, unsubstituted 4-phenyl analog 4a showed Src kinas inhibitory effect with IC50 value of 28.1 μM and was the most potent compound in this series. In general, the compounds were moderately active against BT-20. 3-Nitro-phenyl 4e and 3-pyridinyl 4h derivatives inhibited the cell proliferation of BT-20 cells by 33% and 31.5%, respectively, and found to be more potent compared to doxorubicin (25% inhibition of cell growth). Conclusion: The data indicate that 4-Aryl-4H-naphthopyrans scaffold has the potential to be optimized further for designing more potent Src kinase inhibitors and/or anticancer lead compounds.

Original languageEnglish (US)
Article number100
JournalDARU, Journal of Pharmaceutical Sciences
Volume20
Issue number1
DOIs
StatePublished - 2012
Externally publishedYes

Keywords

  • Anticancer activity
  • Carbonitrile
  • Naphthopyrans
  • Protein kinase
  • Src kinase

ASJC Scopus subject areas

  • Drug Discovery
  • Pharmacology

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    Rafinejad, A., Fallah-Tafti, A., Tiwari, R., Shirazi, A. N., Mandal, D., Shafiee, A., Parang, K., Foroumadi, A., & Akbarzadeh, T. (2012). 4-Aryl-4H-naphthopyrans derivatives: One-pot synthesis, evaluation of Src kinase inhibitory and anti-proliferative activities. DARU, Journal of Pharmaceutical Sciences, 20(1), [100]. https://doi.org/10.1186/2008-2231-20-100