Synthesis and evaluation of a series of C5′-substituted duocarmycin SA analogs

WM Robertson, DB Kastrinsky, I Hwang…

Index: Robertson, William M.; Kastrinsky, David B.; Hwang, Inkyu; Boger, Dale L. Bioorganic and Medicinal Chemistry Letters, 2010 , vol. 20, # 9 p. 2722 - 2725

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Citation Number: 5

Abstract

Duocarmycin SA (1, IC 50 = 10 pM) 1 represents one of the most cytotoxic members of a class of natural products that also include duocarmycin A (2), 2 yatakemycin (3), 3 and CC-1065 (4, Fig. 1). 4 Members of this family of natural products derive their biological properties from a characteristic sequence-selective alkylation of duplex DNA, 5, 6, 7, 8 and 9 in which a stereoelectronically controlled nucleophilic addition of adenine occurs at the least substituted carbon of the ...