臺灣博碩士論文加值系統

依據neocarzinostatin chromophore產生radical的模式合成設計了化合
物propargylsulfone (27),及bis-pro-pargylsulfone (28). 這些
propargylsulfone化合物在鹼性的條件下,能夠產生二或四個自由基.這些
化合物對於癌細胞(Colo 205, HA 22t, SK-BR-3, Molt-4)的生長有很好
的抑制作用.2-(2-phenylethynyl)benzoylazide在苯的溶液中,加入1,4-
cyclohexadiene後經加熱可以得到2-hydroxy-3-phenylquinoline和2-
phenylindole.關於2-hydro-3-phenylquinoline的形成說明如下：enyne-
acylazide經由Curtius重排可以得到enyne-iso-cyanate的中間體產物.此
中間體會環化產生(o,4-dide-hydro-3-phenyl-2-hydroxyquinoline)具有
雙自由基的中間體產物,最後由1,4-cyclohexadiene提供氫原子得到2-
hydroxy-3-phenylquinoline.

Propargylsulfone 27 or bis-propargylsulfone 28 were de-signed as
mimics for the radical-generating system of neocar-zinostatin
chromophore. These propargylsulfone are able togenerate the
intermediate 2 or 4 radicals under the condition ofalkali. Most
of them proved to be active against the growth of cancer cell
lines (Colo 205, Ha 22t, SK-BR-3, Molt-4...etc).Thermolysis of
2-(2-phenylethynyl)benzoyazide in benzenecontaining
1,4-cyclohexadiene gave 2-hydroxy-3-phenyl-quinoline and
2-phenylindole. The formation of 2-hydroxy-3-phenylquinoline was
rationalized as follows: Curtius rearrange-ment of the enyne-
acylazide produces an enyne-isocyanate,subsequent
cycloaromatization forms a biradical intermediate(o,4-
didehydro-3-phenyl-2-hydroxyquinoline) and finallyhydrogen
abstraction from 1,4-cyclohexadiene produces 2-hydroxy-3-
phenylquinoline.