Journal
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
Volume 44, Issue 10, Pages 3915-3921Publisher
ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
DOI: 10.1016/j.ejmech.2009.04.016
Keywords
Naphthofuranoquinone; IBX; Regioselective; Diels-Alder reaction; Cytotoxicity
Categories
Funding
- National High-tech RD 863 Program [2008AA02Z304]
- Science and Technology Key Project of The Education Ministry of PR China [105133]
- Guangdong Provincial Science Foundation [5001773]
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A series of new natural tanshinone-like oxoheterocyclic-fused ortho-quinone derivatives were synthesized from readily available benzofuranol and N-substituted dienes via IBX oxidation-cycloaddition-aromatization procedure. The regiospecific Diels-Alder cycloaddition reactions of N-dienes were achieved efficiently with a variety of dienophiles. It is found that the amide moiety in the molecular could be preserved or eliminated by control of the aromatization conditions. Selected oxoheterocyclic-fused ortho-quinones as well as several thioheterocyclic-fused ortho-quinones we obtained before were evaluated for their cytotoxicities on different cancer cell lines and the Structure-Activity Relationship (SAR) was discussed. (C) 2009 Elsevier Masson SAS. All rights reserved.
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