6-Dialkylaminomethyl-2-phenyl-4-quinolone

• Main Authors: Ju, Chyi-Ren, 朱祺仁
• Other Authors: Kuo Sheng-Chu, Huang Li-Jiau
• Format: Others
• Language: zh-TW
• Published: 1996
• Online Access: http://ndltd.ncl.edu.tw/handle/84212315147874721962

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.