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Nitrosopurines En Route to Potently Cytotoxic Asmarines
Author(s) -
Wan Kanny K.,
Iwasaki Kotaro,
Umotoy Jeffrey C.,
Wolan Dennis W.,
Shenvi Ryan A.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201411493
Subject(s) - pharmacophore , potency , diazepine , purine , stereochemistry , chemistry , cytotoxicity , cytotoxic t cell , combinatorial chemistry , pharmacology , biochemistry , in vitro , biology , organic chemistry , ring (chemistry) , enzyme
A nitrosopurine ene reaction easily assembles the asmarine pharmacophore and transmits remote stereochemistry to the diazepine‐purine hetereocycle. This reaction generates potent cytotoxins which exceed the potency of asmarine A (1.2 μ M IC 50 ) and supersede the metabolites as useful leads for biological discovery.