Abstract
A series of 10 related benzofuran neolignan derivatives were obtained by utilising a biomimetic reaction sequence involving oxidative dimerisation of methyl ferulate, followed by derivatisation reactions. The structures of the new compounds were confirmed by 1H NMR, elemental analysis, MS and IR. All compounds were evaluated for their cytotoxic potential against five human cancer cell lines (HL-60, SMMC-7721, A-549, SK-BR-3 and PAN-1) by the standard MTT method. The results showed that most of them exhibit potent cytotoxicity.
References
1.
Kuo Y.H.
, and
Wu C. H.
, J. Nat. Prod. , 1996 , 59 , 625 .
2.
Yang Z.
,
Liu H. B.
,
Lee C. M.
,
Chang H. M.
, and
Wong H. N. C.
, J. Org. Chem. , 1992 , 57 , 7248 .
3.
Kao C.L.
, and
Chern J. W.
, J. Org. Chem. , 2002 , 67 , 6772 .
4.
Lin S.Y.
,
Chen C. L.
, and
Lee Y. J.
, J. Org. Chem. , 2003 , 68 , 2968 .
5.
Wang Q.A.
,
Zhang Z. J.
,
Zhang C. X.
, and
Fan H. F.
, Chin, J. Org. Chem. , 2008 , 28 , 1605 .
6.
Bose J.S.
,
Gangan V.
,
Prakash R.
,
Jain S. K.
, and
Manna S. K.
, J. Med. Chem. , 2009 , 52 , 3184 .
7.
Wada S.-i.
,
Hitomi T.
, and
Tanaka R.
, Helv. Chim. Acta , 2009 , 92 , 1610 .
8.
Miert S.V.
,
Dyck S. V.
,
Schmidt T. J.
,
Brun R.
,
Vlietinck A.
,
Lemière G.
, and
Pieters L.
, Bioorg. Med. Chem. , 2005 , 13 , 661 .
9.
Kaouadji M.
, and
Favre-Bonvin J.
, Z. Naturforsch., C: Biosci. , 1984 , 39C , 307 .
10.
Rakotondramanana D.L. A.
,
Delomenède M.
,
Baltas M.
,
Duran H.
,
Bedos-Belval F.
,
Rasoanaivo P.
,
Negre-Salvayre A.
, and
Gornitzka H.
, Bioorg. Med. Chem. , 2007 , 15 , 6018 .
11.
Epifano F.
,
Curini M.
,
Genovese S.
,
Blaskovich M.
,
Hamilton A.
, and
Sebti S. M.
, Bioorg. Med. Chem. , 2007 , 17 , 2639 .
12.
Clark M.K.
,
Scott S. A.
,
Wojtkowiak J.
,
Chirco R.
,
Mathieu P.
,
Reiners J. J.
,
Mattingly R. R.
,
Borch R. F.
, and
Gibbs R. A.
, J. Med. Chem. , 2007 , 50 , 3274 .
13.
Talapatra S.K.
,
Mukhopadhyay S. K.
, and
Talapatra B.
, Phytochemistry , 1975 , 14 , 836 .
14.
Maeda S.
,
Masuda H.
, and
Tokoroyama T.
, Chem. Pharm. Bull. , 1994 , 42 , 2500 .
15.
Kaouadji M.
,
Favre-Bonvin J.
, and
Mariotte A. M.
, Phytochemistry , 1978 , 17 , 2134 .
