两种新型二氯代苯基卟啉-5-氟尿嘧啶衍生物的合成与表征

Synthesis and Characterization of Two New Dichloro-Phenyl Porphyrin-5-Fluorouracil Compounds

用5-[4-(5-溴戊氧基)苯基]-10,15,20-三(3,4-二氯苯基)卟啉或5-[4-(6-溴己氧基)苯基]-10,15,20-三(3,4-二氯苯基)卟啉与5-氟尿嘧啶反应,合成了1-[5-(4-戊氧苯基)-10,15,20-三(3,4-二氯苯基)卟啉]-5-氟尿嘧啶(A)和1-[5-(4-己氧苯基)-10,15,20-三(3,4-二氯苯基)卟啉]-5-氟尿嘧啶(B),产率分别为29.92%和30.01%。并通过红外光谱、紫外可见光谱、核磁共振谱和质谱表征了其结构。对目标化合物的合成条件进行了研究,结果表明:以DMF为溶剂,反应温度为115℃,反应时间2h,产率较高;采用硅胶G(200—300目)装柱,以氯仿和氯仿∶乙醚(V∶V=50∶1)为洗脱液,柱层析,再用氯仿:丙酮(V∶V=7∶1)洗脱产品色带,分离效果较好。

1-[-5-（4-pentaphenoxy） phenyl-10, 15, Z0-tri （3, 4-dichlorophenyl） porphyrin]-5- fluorouraeil （ A ）, 1-[ 5- （ 4-hexaphenoxy ） phenyl-10, 15, 20-tri （3, 4-dichlorophenyl ） porphyrin ]-5- fluorouracil （B ） were synthesized from 5- [ 4- （5-bromo-pentaphenoxy） phenyl ]- 10, 15, 20-tri （ 3,4- dichlorophenyl ） porphyrin or 5-[ 4-（ 6-bromo-hexaphenoxy ） phenyl ]-10, 15, 20-tri （ 3, 4- dichlorophenyl） porphyrin, and characterized by UV-Vis, IR, ^1HNMR and MS. The synthesis and separation conditions of the target compounds were studied. The yields were higher with DMF as the solvent at 115℃ for 2h. The products were separated via column chromatography with silica gel （200--300） with chloroform, chloroform-ether （V ： V = 50： 1） and chloroform-acetone （V ： V = 7 ： 1）as the eluent when the column was 3 cm in diameter and 10 cm in hight.