Enediyne Quinone Imines: Truncated, Biologically Active Dynemicin Congeners | Zendy

Shair Matthew D. | Zendy; Danishefsky Samuel J. | Zendy; Yoon Taeyoung | Zendy; Chou TingChao | Zendy

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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.

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