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

Kazunobu Toshima, Kazumi Ohta, Takaaki Kano, Takatsugu Nakamura, Masaya Nakata, Mitsuhiro Kinoshita, Shuichi Matsumura

研究成果: Article査読

12 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)105-113
ページ数9
ジャーナルBioorganic and Medicinal Chemistry
4
1
DOI
出版ステータスPublished - 1996 1月

ASJC Scopus subject areas

  • 生化学
  • 分子医療
  • 分子生物学
  • 薬科学
  • 創薬
  • 臨床生化学
  • 有機化学

フィンガープリント

「Novel designed enediynes: Molecular design, chemical synthesis, mode of cycloaromatization and guanine-specific DNA cleavage」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル