| 摘要: | 中文摘要 為了探討6-fluorinated-2-phenylquinolin-4-one derivatives之抗有絲分裂的活性，著者合成了3’-substituted 6-fluoro- 2-phenylquinolin-4-one-3-carboxylic acids(22, 23, 24, 25) and 3’-substituted 6-fluoro-2-phenylquinolin-4-ones (26, 27, 28)。 合成中間體，substituted benzo-p-fluorophenyl imidoyl chlorides (10~13)，是由N-(p-fluorophenyl) substituted benzamides (6,7,8,9) 和PCl5反應來製備而成的，所得到之p-halobenzo p-fluorophenyl imidoyl chlorides (10, 11) 和 sodium diethylmalonate ,經縮合後，再熱環化後即可得到相對應的deethoxy carbonylation產物(26,27),而不是預期的產物(18,19)。然而，當benzo p-fluorophenyl imidoyl chloride (12)和p-methoxybenzo p-fluorophenyl imidoyl chloride (13)在相同的步驟下，當作起始物質，獲得到預期的產物 ethyl 6-fluoro-2-phenylquinolin-4-one-3-carboxylate (20)和 ethyl 3’-methoxy-6-fluoro-2-phenylquinolin-4-one-3-carboxylate (21)，將化合物20與21用氫氧化鈉來水解,分別地得到6-fluoro-2-phenylquinolin-4-one-3-carboxylic acid (24)與3’- methoxy-6-fluoro-2-phenylquinolin-4-one-3-carboxylic acid(25)。; Summary In order to examine the antimitotic activities of 6-fluorinated 2-phenylquinolin-4-one derivatives , synthesis of 3’-substituted 6-fluoro -2-phenylquinolin-4-one-3-carboxylic acids (22, 23, 24) and 3’- substituted 6-fluoro-2-phenylquinolin-4-ones (26, 27, 28) were carried out. Substituted benzo p-fluorophenyl imidoyl chlorides (10~13) were prepared by reaction of N-(p-fluorophenyl) substituted benzamides (6,7,8,9) with phosphorus pentachloride. Condensation of p-halobenzo p-fluorophenyl imidoyl chlorides (10,11) with sodium diethylmalonate, followed by thermal cyclization respectively , resulted the corresponding deethoxy carbonylation products (26,27), instead of the expected products (18,19). However, when benzo p-fluorophenyl imidoyl chloride (12) and p-methoxybenzo p-fluorophenyl imidoyl chloride (13) were used as a starting material in the same procedure, the expected ethyl 6-fluoro -2-phenylquinolin-4-one-3-carboxylate (20) and ethyl 3’-methoxy -6-fluoro -2-phenylquinolin-4-one-3-carboxylate (21) were obtained. Hydrolysis of compounds 20 and 21 with sodium hydroxide afford 6-fluoro-2-phenylquinolin-4-one-3-carboxylic acid (24) and 3’-methoxy -6-fluoro-2-phenylquinolin-4-one-3-carboxylic acid (25) respectively. |
