Synthesis, reactions and DNA damaging abilities of 10-membered enediyne-sulfone and related compounds

…, A Shigenaga, A Manabe, H Nemoto, M Shibuya

Index: Suzuki, Ichiro; Shigenaga, Akira; Manabe, Atsuo; Nemoto, Hisao; Shibuya, Masayuki Tetrahedron, 2003 , vol. 59, # 30 p. 5691 - 5704

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Citation Number: 12

Abstract

The synthesis and Myers–Saito type cycloaromatization reactions of 10-membered enediynes containing a sulfone or a sulfoxide moiety are described. These enediynes cycloaromatized smoothly under physiological conditions to generate bioactive α, 3- didehydrotoluene biradicals, that showed potent DNA damaging abilities. Further, in the presence of a nucleophile such as amine or sulfide, cycloaromatization did not occur ...