Synthesis and antiproliferative and c-Src kinase inhibitory activities of cinnamoyl-and pyranochromen-2-one derivatives

Karam Chand, Amir Nasrolahi Shirazi, Preeti Yadav, Rakesh K. Tiwari, Meena Kumari, Keykavous Parang, Sunil K. Sharma

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish (US)
Pages (from-to)741-754
Number of pages14
JournalCanadian Journal of Chemistry
Volume91
Issue number8
DOIs
StatePublished - Aug 2013
Externally publishedYes

Fingerprint

Chalcone
src-Family Kinases
Cells
Derivatives
Cell proliferation
Antineoplastic Agents
CSK tyrosine-protein kinase
flavanone

Keywords

  • Anticancer
  • Antiproliferative
  • C-Src kinase
  • Chromen-2-one

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Catalysis

Cite this

Synthesis and antiproliferative and c-Src kinase inhibitory activities of cinnamoyl-and pyranochromen-2-one derivatives. / Chand, Karam; Shirazi, Amir Nasrolahi; Yadav, Preeti; Tiwari, Rakesh K.; Kumari, Meena; Parang, Keykavous; Sharma, Sunil K.

In: Canadian Journal of Chemistry, Vol. 91, No. 8, 08.2013, p. 741-754.

Research output: Contribution to journalArticle

Chand, Karam ; Shirazi, Amir Nasrolahi ; Yadav, Preeti ; Tiwari, Rakesh K. ; Kumari, Meena ; Parang, Keykavous ; Sharma, Sunil K. / Synthesis and antiproliferative and c-Src kinase inhibitory activities of cinnamoyl-and pyranochromen-2-one derivatives. In: Canadian Journal of Chemistry. 2013 ; Vol. 91, No. 8. pp. 741-754.
@article{925dd8726cba46a7b1de4506626a0e33,
title = "Synthesis and antiproliferative and c-Src kinase inhibitory activities of cinnamoyl-and pyranochromen-2-one derivatives",
abstract = "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.",
keywords = "Anticancer, Antiproliferative, C-Src kinase, Chromen-2-one",
author = "Karam Chand and Shirazi, {Amir Nasrolahi} and Preeti Yadav and Tiwari, {Rakesh K.} and Meena Kumari and Keykavous Parang and Sharma, {Sunil K.}",
year = "2013",
month = "8",
doi = "10.1139/cjc-2013-0053",
language = "English (US)",
volume = "91",
pages = "741--754",
journal = "Canadian Journal of Chemistry",
issn = "0008-4042",
publisher = "National Research Council of Canada",
number = "8",

}

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

UR - http://www.scopus.com/inward/record.url?scp=84880753846&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84880753846&partnerID=8YFLogxK

U2 - 10.1139/cjc-2013-0053

DO - 10.1139/cjc-2013-0053

M3 - Article

AN - SCOPUS:84880753846

VL - 91

SP - 741

EP - 754

JO - Canadian Journal of Chemistry

JF - Canadian Journal of Chemistry

SN - 0008-4042

IS - 8

ER -