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Novel designed enediynes: molecular design, chemical synthesis, mode of cycloaromatization and guanine-specific DNA cleavage.

Abstract：

:The molecular design and chemical synthesis of novel enediyne molecules related to the neocarzinostatin chromophore (1), and their chemical and DNA cleaving properties are described. The 10-membered enediyne triols 16-18 were effectively synthesized from xylitol (10) in a short step, and found to be quite stable when handled at room temperature. The representative and acylated enediyne 16 was cycloaromatized by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in cyclohexa-1,4-diene-benzene to give the benzenoid product 21 through a radical pathway. On the other hand, the enediyne 16 was cycloaromatized by diethylamine in dimethyl sulfoxide-Tris-HCl, pH 8.5 buffer to afford another benzenoid product 22 as a diethylamine adduct through a polar pathway. Furthermore, the enediynes 16-18 were found to exhibit guanine-specific DNA cleavage under weakly basic conditions with no additive.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Toshima K,Ohta K,Kano T,Nakamura T,Nakata M,Kinoshita M,Matsumura S

doi

10.1016/0968-0896(95)00170-0

subject

Has Abstract

pub_date

1996-01-01 00:00:00

pages

105-13

issue

1

eissn

0968-0896

issn

1464-3391

pii

0968089695001700

journal_volume

4

pub_type

杂志文章

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