| Summary: | 碩士 === 中國醫藥學院 === 藥物化學研究所 === 84 === 6-比啶烷基-3'-甲氧基-2-苯基-4-奎林酮具有非常優越之細胞致毒
活性,本研究為了檢測其結構活性關係,一個相近標的物6-
alkylaminomethyl-2-phenyl-4-quinolone之合成途徑已成功的建立起來
了o 檢試6-alkylaminomethyl-2-phenyl-4-quinolone 之合成法,找到
下列步驟為最恰當之方法o 將6-methyl-2-phenyl-4-quinolone 於乾
燥的DMF以NaH處理後,再加入氯化甲苯反應,即可得到4-benzyloxy-6-
methyl-2-phenylquinoline,再將其以NBS 和AIBN 溴化, 接著再與二甲基
胺反應, 即可得到4-benzyloxy-6-dimethylaminomethyl-2-
phenylquinoline. 然後,此化合物以催化性氫化還原反應即成6-二甲基胺
甲基-2-苯基-4-奎林酮o
In oder to examine the SAR of 6-pyrrolidinyl-3'-methoxy-2-
phenyl-4-quinolone which possess potent cytotoxicity, a
synthetic approch to thetarget compound 6-dimethylaminomethyl-2-
phenyl-4-quinolone was carried out. Examination of methods
for the synthesis of 6-alkylaminomethyl-2-phenyl-4-quinolone
showedthat the following route was found to be the most
approciate. When 6-methyl-2-phenyl-4-quinolone was treated
with NaH in dry DMF followed by reaction with benzyl chloride,
4-benzyloxy-6-methyl-2-phenyl-quinoline was obtained.
Bromination of 4-benzyloxy-6-methyl-2-phenylquinoline with NBS
in the present of AIBN,followed by reaction with
dimethylamine,4-benzyloxy-6-dimethylaminomethyl-2-
phenylquinoline was obtained.4-Benzyloxy-6-
dimethylaminomethyl-2-phenylquinoline was then reduced to the
objective 6-dimethylaminomethyl-2-phenyl-4-quinolone by catalyst
hydrogenation.
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