Abstract
The syntheses of four 2-substituted 1,4 naphthoquinones, related to the marine natural product 2-deoxylapachol, are reported. All four synthetic compounds were cytotoxic to WHCO1 oesophageal cancer cells.
References
1.
Subramanian S.
,
Ferreira M.M.C.
, and
Trsic M.
, Structural Chem. , 1998 , 9 , 47 .
2.
Mqoqi N.
,
Kellett P.
,
Madhoo J.
, and
Sitas F.
(2003 ). National Cancer Registry of South Africa. Incidence and geographical distribution of histologically diagnosed cancer in South Africa, 1996-1997. South African Institute for Medical Research , Johannesburg .
3.
Pickens A.
, and
Orringer M.B.
, Ann. Thorac. Surg. , 2003 , 76 , 1367 .
4.
Whibley C.E.
,
Keyzers R.A.
,
Soper A.G.
,
Davies-Coleman M.T.
,
Samaai T.
, and
Hendricks D.T.
, Annls N.Y. Acad. Sci. , 2005 , 1056 , 405 .
5.
Perry N.B.
,
Blunt J.W.
, and
Munro M.H.G.
, J. Nat. Prod. , 1991 , 54 , 978 .
6.
Kraus G.A.
, and
On Man T.
, Synth. Commun. , 1986 , 16 , 1037 .
7.
Chen Y.
, and
Chang W.
, J. Org. Chem. , 1996 , 61 , 2536 .
8.
Nquyen Van T.
,
Kesteleyn B.
, and
De Kimpe N.
, Tetrahedron , 2001 , 57 , 4213 .
9.
Kobayashi K.
,
Uchida M.
,
Uneda T.
,
Yoneda K.
,
Tanmatsu M.
,
Morikawa O.
, and
Konishi H.
, J. Chem. Soc., Perkin Trans. 1 , 2001 , 2977 .
10.
Tsai A.
,
Wu Y.
, and
Chuang C.
, Tetrahedron , 2001 , 57 , 7829 .
11.
Ragoussis N.
, Tetrahedron Lett. , 1987 , 28 , 93 .
12.
Jacobsen N.
, and
Torssell K.
, Acta. Chem. Scan. , 1973 , 27 , 3211 –3216 .
13.
Claessens S.
,
Kesteleyn B.
,
Nguyen Van T.
, and
De Kimpe N.
, Tetrahedron , 2006 , 62 , 8419 .
14.
Hagiwara E.
,
Hatanaka Y.
,
Gohda K.
, and
Hiyama T.
, Tetrahedron Lett. , 1995 , 36 , 2773 .
15.
Rajput J.
,
Moss J.R.
,
Hutton A.T
,
Hendricks D.T.
,
Arendse C.E.
, and
Imrie C.
, J. Organomet. Chem. , 2004 , 689 , 1553 .
16.
Whibley C.E.
,
McPhail K.L.
,
Keyzers R.A.
,
Maritz M.F.
,
Leaner V.D.
,
Davies-Coleman M.T.
, and
Hendricks D.T.
, Mol. Cancer Ther. , 2007 , 6 , 2535 .
17.
Evans P.A.
, and
Brandt T.A.
, J. Org. Chem. , 1997 , 62 , 5321 .
18.
Tanoue Y.
,
Terada A.
, and
Matsumoto Y.
, Bull. Chem. Soc. Jpn. , 1989 , 62 , 2736 .
19.
Uno H.
, J. Org. Chem. , 1986 , 51 , 350 .
20.
Giles R.G.F.
,
Green I.R.
,
Hugo V.I.
,
Mitchell P.R.K.
, and
Yorke S.C.
, J. Chem. Soc. Perkin Trans 1 , 1983 , 2309 .