This work was supported by the National Institutes of Health (Grant CA 28824). A predoctoral fellowship from Memorial Sloan-Kettering Cancer Center to M.D.S. is gratefully acknowledged. We thank Professor A. G. Myers for an advanced copy of his manuscript in which related developments are described.
Enediyne Quinone Imines: Truncated, Biologically Active Dynemicin Congeners†
Article first published online: 22 DEC 2003
Copyright © 1994 by VCH Verlagsgesellschaft mbH, Germany
Angewandte Chemie International Edition in English
Volume 33, Issue 23-24, pages 2477–2479, January 3, 1995
How to Cite
Shair, M. D., Danishefsky, S. J., Yoon, T. and Chou, T.-C. (1995), Enediyne Quinone Imines: Truncated, Biologically Active Dynemicin Congeners. Angew. Chem. Int. Ed. Engl., 33: 2477–2479. doi: 10.1002/anie.199424771
- Issue published online: 22 DEC 2003
- Article first published online: 22 DEC 2003
- Manuscript Revised: 10 OCT 1994
- Manuscript Received: 19 AUG 1994
An intermediate in the total synthesis of dynemicin A, quinone imine 1 can be used as a dienophile. But 1 is also a potent cytotoxic agent against human cancer cell lines since it is able to cleave DNA. In vitro and in vivo studies showed that 1 is more effective than two frequently applied antitumor drugs. Quinone imine 1 was synthesized by the rapid oxidation of a fleeting hydroisoquinone intermediate.