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Enediyne Quinone Imines: Truncated, Biologically Active Dynemicin Congeners
Author(s) -
Shair Matthew D.,
Danishefsky Samuel J.,
Yoon Taeyoung,
Chou TingChao
Publication year - 1995
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199424771
Subject(s) - quinone , enediyne , imine , chemistry , stereochemistry , in vivo , in vitro , cleave , biological activity , dna , combinatorial chemistry , biochemistry , biology , genetics , catalysis
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.