679394-70-8

Basic information

• Product Name: 2-[(3,4-dimethoxybenzylidene)amino]-1H-benzimidazole
• Synonyms: 2-[(3,4-dimethoxybenzylidene)amino]-1H-benzimidazole
• CAS NO: 679394-70-8
• Molecular Weight: 281.314
• Mol File: 679394-70-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-[(3,4-dimethoxybenzylidene)amino]-1H-benzimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(3,4-dimethoxybenzylidene)amino]-1H-benzimidazole(679394-70-8)
• EPA Substance Registry System: 2-[(3,4-dimethoxybenzylidene)amino]-1H-benzimidazole(679394-70-8)

Safety Data

• Hazardous Substances Data: 679394-70-8(Hazardous Substances Data)

Upstream product

• 934-32-7 1H-benzimidazol-2-amine 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

• 345368-42-5 α-cyano-3,4-dimethoxycinnamic acid benzylamide 
• 2286-55-7 ethyl α-cyano-β-(3,4-dimethoxyphenyl)acrylate 
• 19310-63-5 α-cyano-2,4-dimethoxycinnamic amide 
• 1048974-63-5 4-amino-2-(3,4-dimethoxyphenyl)-1,2-dihydropyrimido[1,2-a]benzimidazole-3-carbonitrile 
• 1064084-16-7 2-(3,4-dimethoxyphenyl)-3-(ethoxycarbonyl)-4-methyl-1,2-dihydropyrimido[1,2-a]benzimidazole 
• 1064084-43-0 3-(tert-butoxycarbonyl)-2-(3,4-dimethoxyphenyl)-4-methyl-1,2-dihydropyrimido[1,2-a]benzimidazole 

Relevant articles and documents

Synthesis and antiproliferative activity in vitro of new 2-aminobenzimidazole derivatives. Reaction of 2-arylideneaminobenzimidazole with selected nitriles containing active methylene group

A series of pyrimido[1,2-a]benzimidazole and a-cyanocinnamic acid derivatives have been synthesized in the reactions of Schiff bases 2-7 with selected nitriles containing an active methylene group: malononitrile 8-12, cyanoacetamide 13-16, benzyl cyanide 17-21, benzoylacetonitrile 22-24, cyanoacetate methyl ester 25-28 and benzylacetamide 29. The structures 8-29 were confirmed by the results of elementary analysis and their IR, 1H-, 13C-NMR and MS spectra. The products 8-29 of various chemical structure pyrimido[1,2-a] benzimidazole 8-12, 14-16, 17-21, 23-24, 26 and a-cyanocinnamic acid derivatives 13, 22, 25, 27, 28 were obtained, which are of interest for biological studies or which can be substrates for further synthesis. The selected compounds 10, 13, 14, 17, 19, 21, 23-25 and 28 were screened for their antiproliferative activity in vitro against neoplastic and normal cell lines. The most active two compounds were: 2-(o-bromophenylene)-3-cyano-4-phenyl-1,2-dihydropyrimido[1,2-a] benzimidazole (24) and 3-cyano-4-phenyl-2-(2,4-dimethoxyphenyl)-1,2- dihydropyrimido[1,2-a]benzimidazole (23). However, similarly like cisplatin used as the control, they showed no selectivity towards cancer cells, by inhibiting proliferation of normal mouse fibroblasts in similar manner. Versita Sp. z o.o.

Synthesis and antiproliferative activity in vitro of 2-aminobenzimidazole derivatives

A novel series of Schiff bases 1-11, the derivatives of 2-aminobenzimidazole and substituted aromatic aldehydes, has been synthesised. Compounds 1-11 reduced by NaBH4 formed 2-benzylaminobenzimidazoles 12-21. 2-(o-Bromobenzylamino)benzimidazole (15) acylated by cinnamoyl chloride gave 2-(o-bromobenzylamino)-1-cinnamoylbenzimidazole (22). Long heating of 15 and 19 with p-nitrocinnamoyl or cinnamoyl chloride led to the formation of pyrimido[1,2-a]benzimidazol-4-ones 23 and 24. The structures of 1-24 were identified by the results of elemental analysis and their IR, 1H NMR and MS spectra. Among the compounds 1-24 evaluated for their antiproliferative activity in vitro, 16, 19, 20 and 22 exhibited cytotoxic activity against the cells of human cancer cell lines, namely SW707 (rectal), HCV29T (bladder), A549 (lung) and T47D (breast cancer).