Abstract
Nine chalcone derivatives containing an N-heterocyclic compound attached by its nitrogen atom to one of the benzene rings were prepared and evaluated for their antiproliferative activity against liver, gastric and neuroendocrine cancer cell lines. Most of the synthesised compounds exhibited moderate to good activity against all three cancer cell lines, but in particular, a chalcone containing a 4-(imidazol-1-yl)phenyl group and a 3,4,5-trimethoxyphenyl group showed the highest antiproliferative activity with an IC50 value of 5.39 μM against liver cancer cells.
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References
1.
Pirali T.
,
Busacca S.
,
Beltrami L.
,
Imovilli D.
,
Pagliai F.
,
Miglio G.
,
Massarotti A.
,
Verotta L.
,
Tron G. C.
,
Sorba G.
, and
Genazzani A. A.
, J. Med. Chem. , 2006 , 49 , 5372 .
2.
Spatafora C.
, and
Tringali C.
, Anticancer Agents Med. Chem. , 2012 , 12 , 902 .
3.
Kong Y.
,
Wang K.
,
Edler M. C.
,
Hamel E.
,
Mooberry S. L.
,
Paige M. A.
, and
Brown M. L.
, Bioorg. Med. Chem. , 2010 , 18 , 971 .
4.
Alcaráz L.
,
Blanco S.
,
Puig O.
,
Tomás F.
, and
Ferretti F.
, J. Theor. Biol. , 2000 , 205 , 231 .
5.
Mallavadhani U.
,
Sahoo L.
,
Kumar K.
, and
Murty U.
, Med. Chem. Res. , 2014 , 23 , 2900 .
6.
Awoussong P.
,
Zaharia V.
,
Ngameni B.
,
Kuete V.
,
Ntede H.
,
Fokunang C.
,
Abegaz B.
, and
Ngadjui B.
, Med. Chem. Res. , 2015 , 24 , 131 .
7.
Sharma P.
,
Kumar S.
,
Ali F.
,
Anthal S.
,
Gupta V.
,
Khan I.
,
Singh S.
,
Sangwan P.
,
Suri K.
,
Gupta B.
,
Gupta D.
,
Dutt P.
,
Vishwakarma R.
, and
Satti N.
, Med. Chem. Res. , 2013 , 22 , 3969 .
8.
Nowakowska Z.
, Eur. J. Med. Chem. , 2007 , 42 , 125 .
9.
Hsieh H.-K.
,
Lee T.-H.
,
Wang J.-P.
,
Wang J.-J.
, and
Lin C.-N.
, Pharm. Res. , 1998 , 15 , 39 .
10.
Wu J.-Z.
,
Cheng C.-C.
,
Shen L.-L.
,
Wang Z.-K.
,
Wu S.-B.
,
Li W.-L.
,
Chen S.-H.
,
Zhou R.-P.
, and
Qiu P.-H.
, Int. J. Mol. Sci. , 2014 , 15 , 18525 .
11.
Vasil'ev R.F.
,
Kancheva V. D.
,
Fedorova G. F.
,
Batovska D. I.
, and
Trofimov A. V.
, Kinet. Catal. , 2010 , 51 , 507 .
12.
Ducki S.
,
Rennison D.
,
Woo M.
,
Kendall A.
,
Chabert J. F.
,
McGown A. T.
, and
Lawrence N. J.
, Bioorg. Med. Chem. , 2009 , 17 , 7698 .
13.
Fu D.-J.
,
Zhang S.-Y.
,
Liu Y.-C.
,
Song J.
,
Zhao R.-H.
,
Mao R.-W.
,
Liu H.-M.
, and
Zhang Y.-B.
, J. Chem. Res. , 2016 , 40 , 624 .
14.
Chavva K.
,
Pillalamarri S.
,
Banda V.
,
Gautham S.
,
Gaddamedi J.
,
Yedla P.
,
Kumar C. G.
, and
Banda N.
, Bioorg. Med. Chem. Lett. , 2013 , 23 , 5893 .
15.
Cherfaoui B.
,
Guo T. K.
,
Sun H. P.
,
Cheng W. L.
,
Liu F.
,
Jiang F.
,
Xu X. L.
, and
You Q. D.
, Bioorg. Med. Chem. , 2016 , 24 , 2423 .
16.
Yin Y.
,
Qiao F.
,
Jiang L. Y.
,
Wang S. F.
,
Sha S.
,
Wu X.
,
Lv P. C.
, and
Zhu H. L.
, Bioorg. Med. Chem. , 2014 , 22 , 4285 .
17.
Zheng Y.-C.
,
Duan Y.-C.
,
Ma J.-L.
,
Xu R.-M.
,
Zi X.
,
Lv W.-L.
,
Wang M.-M.
,
Ye X.-W.
,
Zhu S.
,
Mobley D.
,
Zhu Y.-Y.
,
Wang J.-W.
,
Li J.-F.
,
Wang Z.-R.
,
Zhao W.
, and
Liu H.-M.
, J. Med. Chem. , 2013 , 56 , 8543 .
18.
Alvarez G.
,
Aguirre-Lopez B.
,
Cabrera N.
,
Marins E. B.
,
Tinoco L.
,
Batthyany C. I.
,
de Gomez-Puyou M. T.
,
Puyou A. G.
,
Perez-Montfort R.
,
Cerecetto H.
, and
Gonzalez M.
, J. Enzyme Inhib. Med. Chem. , 2013 , 28 , 981 .