Synthesis of 5-substituted 2-methylbenzimidazoles with anticancer activity.
A series of compounds comprising the thiocarboximidopyrazolyl 5, the phenylpyrazolyl 6, the dimethylpyrazolyl 7, the nitrophenylpyrazolyl 8, the dimethyloxazolyl 9, the benzoxazepinyl 10, and pyrimidyl 11 a-c derivatives of 3-(2-methyl-1H-benzimidazol-5-ylazo)pentane-2, 4-dione was synthesized. Moreover, 5-amino-2-methylbenzimidazole (3) was reacted with phthalic anhydride or maleic anhydride in acetic acid or in toluene to produce 12-15. Treating 5, 6-diamino-2-methylbenzimidazole (16) with ethyl cyanoacetate or diethyl malonate or acetyl acetone leads to the formation of the benzodiazepine derivatives 17-20. The cytotoxic activity of the compounds 2, 7, 9, 10, and 11 was tested against 60 types of human cancer cell lines. Compounds 7 and 9 were found to be the most potent.
el-Naem
Sh I
ShI
Chemistry of Natural and Microbial Products Department, National Research Centre, Dokki, Cairo, Egypt. heldiway@hotmail.com
el-Nzhawy
A O
AO
el-Diwani
H I
HI
Abdel Hamid
A O
AO
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use; D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use; D004305:Dose-Response Relationship, Drug; D006801:Humans; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured / Q000187:drug effects*
D000970:Antineoplastic Agents; D001562:Benzimidazoles