TY - JOUR
T1 - Synthesis and antiproliferative and c-Src kinase inhibitory activities of cinnamoyl-and pyranochromen-2-one derivatives
AU - Chand, Karam
AU - Shirazi, Amir Nasrolahi
AU - Yadav, Preeti
AU - Tiwari, Rakesh K.
AU - Kumari, Meena
AU - Parang, Keykavous
AU - Sharma, Sunil K.
PY - 2013/8
Y1 - 2013/8
N2 - A series of 6-and 8-cinnamoylchromen-2-one and dihydropyranochromen-2-one derivatives were synthesized and their antiproliferative activities were evaluated against three human cancer cell lines, i.e., ovarian adenocarcinoma (SK-OV-3), leukemia (CCRF-CEM), and breast carcinoma (MCF-7). In general, 8-cinnamoylchromen-2-one derivatives were found to have higher antiproliferative activity against the cancer cells when compared with 6-cinnamoyl analogues. Among all of the hybrid chromen-2-one-chalcone/flavanone compounds, a 7-hydroxy-8-cinnamoylchromen-2-one derivative 35 was found to be consistently active against all the cancer cell lines and inhibited the cell proliferation of SK-OV-3, CCRF-CEM, and MCF-7 by 63%, 50%, and 43%, respectively, at a concentration of 50 μmol/L after 72 h of incubation. This compound also exhibited the highest Src kinase inhibition (IC50 = 14.5 μmol/L). Structure-activity relationship studies provided insights for designing the next generation of chromen-2-one-chalcone hybrid prototypes and the development of new leads as anticancer agents and (or) Src kinase inhibitors.
AB - A series of 6-and 8-cinnamoylchromen-2-one and dihydropyranochromen-2-one derivatives were synthesized and their antiproliferative activities were evaluated against three human cancer cell lines, i.e., ovarian adenocarcinoma (SK-OV-3), leukemia (CCRF-CEM), and breast carcinoma (MCF-7). In general, 8-cinnamoylchromen-2-one derivatives were found to have higher antiproliferative activity against the cancer cells when compared with 6-cinnamoyl analogues. Among all of the hybrid chromen-2-one-chalcone/flavanone compounds, a 7-hydroxy-8-cinnamoylchromen-2-one derivative 35 was found to be consistently active against all the cancer cell lines and inhibited the cell proliferation of SK-OV-3, CCRF-CEM, and MCF-7 by 63%, 50%, and 43%, respectively, at a concentration of 50 μmol/L after 72 h of incubation. This compound also exhibited the highest Src kinase inhibition (IC50 = 14.5 μmol/L). Structure-activity relationship studies provided insights for designing the next generation of chromen-2-one-chalcone hybrid prototypes and the development of new leads as anticancer agents and (or) Src kinase inhibitors.
KW - Anticancer
KW - Antiproliferative
KW - C-Src kinase
KW - Chromen-2-one
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U2 - 10.1139/cjc-2013-0053
DO - 10.1139/cjc-2013-0053
M3 - Article
AN - SCOPUS:84880753846
SN - 0008-4042
VL - 91
SP - 741
EP - 754
JO - Canadian Journal of Chemistry
JF - Canadian Journal of Chemistry
IS - 8
ER -