TY - JOUR
T1 - 4-Aryl-4H-naphthopyrans derivatives
T2 - One-pot synthesis, evaluation of Src kinase inhibitory and anti-proliferative activities
AU - Rafinejad, Ali
AU - Fallah-Tafti, Asal
AU - Tiwari, Rakesh
AU - Shirazi, Amir Nasrolahi
AU - Mandal, Deendayal
AU - Shafiee, Abbas
AU - Parang, Keykavous
AU - Foroumadi, Alireza
AU - Akbarzadeh, Tahmineh
PY - 2012
Y1 - 2012
N2 - 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.
AB - 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.
KW - Anticancer activity
KW - Carbonitrile
KW - Naphthopyrans
KW - Protein kinase
KW - Src kinase
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U2 - 10.1186/2008-2231-20-100
DO - 10.1186/2008-2231-20-100
M3 - Article
C2 - 23351304
AN - SCOPUS:84878544941
VL - 20
JO - Daru
JF - Daru
SN - 1560-8115
IS - 1
M1 - 100
ER -