Wojcicka Anna, Becan Lilianna, Junka Adam, Brtoszewicz Marzenna, Secewicz Anna, Trynda Justyna, Wietrzyk Joanna
Acta Pol Pharm. 2017 Mar;74(2):435-443.
The new pyrrolo[3,4-c]pyridines have been synthesized. 4-Methyl-6-phenyl-1H-pyrrolo[3,4-cpyridine-1,3-dione (1) was the key intermediate for the synthesis of the novel derivatives of various chemical structures. In the first step, the pyrrolo[3,4-c]pyridine-1,3-dione 1 was alkylated to the corresponding N-alkyl-4- methyl-6-phenyl-IH-pyrrolo[3,4-c]pyridine-1,3-dione derivatives 2a-f. The Mannich bases 3a-j were synthesized by treating pyrrolo[3,4-c]pyridine-1,3-dione 1 with appropriate amines and formaldehyde. Hydrolysis of ester 2a gave the appropriate acid 5. Next, amides 4a-e have been obtained. The structures of the new compounds were confirmed by elemental analysis, IR and NMR spectra. The antitumor and antimicrobial activities in vitro of the obtained derivatives were examined. Mannich bases 3c and 3g showed activity against C. albicans and S. aureus.
新型吡咯并[3,4-c]吡啶已被合成。4-甲基-6-苯基-1H-吡咯并[3,4-c]吡啶-1,3-二酮(1)是合成各种化学结构新型衍生物的关键中间体。第一步,将吡咯并[3,4-c]吡啶-1,3-二酮1烷基化,得到相应的N-烷基-4-甲基-6-苯基-1H-吡咯并[3,4-c]吡啶-1,3-二酮衍生物2a-f。通过用适当的胺和甲醛处理吡咯并[3,4-c]吡啶-1,3-二酮1合成了曼尼希碱3a-j。酯2a水解得到相应的酸5。接下来,得到了酰胺4a-e。通过元素分析、红外光谱和核磁共振光谱确定了新化合物的结构。对所得衍生物的体外抗肿瘤和抗菌活性进行了研究。曼尼希碱3c和3g对白色念珠菌和金黄色葡萄球菌显示出活性。