167959-16-2

Upstream product

• 167959-15-1 2'-(4-Methoxy-phenyl)-1H,3'H-[2,5']bibenzoimidazolyl-5-carbonitrile 
• 391903-20-1 2-(4-methoxy-phenyl)-1H-benzimidazole-6-carboxylic acid methoxy-methylamide 
• 391903-21-2 2'-(4-methoxy-phenyl)-[2,6'] bis(1H-benzoimidazole)-6-carboxylic acid 
• 391903-19-8 N-methoxy N-methyl 3,4-dinitrobenzoic acid amide 
• 660432-02-0 N-methoxy N-methyl 3,4-diaminobenzoic acid amide 
• 619-05-6 3,4-diaminobenzoic acid 
• 126824-21-3 5-(Hydroxymethyl)-2-(4-methoxyphenyl)-1H-benzimidazole 
• 126824-22-4 2-(4-methoxyphenyl)-1H-benzo[d]imidazole-6-carbaldehyde 
• 24376-18-9 3,4-dinitrobenzoyl chloride 
• 37466-90-3 ethyl 3,4-diaminobenzoate 
• 528-45-0 3,4-dinitrobenzoic acid 
• 391903-22-3 2'-(4-methoxy-phenyl)-[2,6'] bis(1H-benzoimidazole)-6-carboxylic acid methoxy-methyl amide 
• 6393-40-4 4-Amino 3-nitro-benzonitrile 
• 167959-14-0 5-cyano-2-(p-methoxyphenyl)benzimidzole 

Relevant academic research and scientific papers

Tris-benzimidazole derivatives: Design, synthesis and DNA sequence recognition

Two tris-benzimidazole derivatives have been designed and synthesized based on the known structures of the bis-benzimidazole stain Hoechst 33258 complexed to short oligonucleotide duplexes derived from single crystal X-ray studies and from NMR. In both derivatives the phenol group has been replaced by a methoxy-phenyl substituent. Whereas one tris-benzimidazole carries a N-methyl-piperazine at the 6-position, the other one has this group replaced by a 2-amino-pyrrolidine ring. This latter substituent results in stronger DNA binding. The optimized synthesis of the drugs is described. The two tris-benzimidazoles exhibit high AT-base pair (bp) selectivity evident in footprinting experiments which show that five to six base pairs are protected by the tris-benzimidazoles as compared to four to five protected by the bis-benzimidazoles. The tris-benzimidazoles bind well to sequences like 5′-TAAAC, 5′-TTTAC and 5′-TTTAT, but it is also evident that they can bind weakly to sequences such as 5′-TATGTT-3′ where the continuity of an AT stretch is interrupted by a single G·C base pair.

Synthesis and evaluation of terbenzimidazoles as topoisomerase I inhibitors

The synthesis and pharmacological activity of a series of terbenzimidazoles are described. The ability of these derivatives to induce DNA cleavage in the presence of topoisomerase I was evaluated in vitro. These analogs were also assayed for their cytotoxicity in RPMI 8402 cells and the camptothecin-resistant CPT-K5 cells. In addition the potential for these compounds to serve as substrates for MDR1 was also determined. Several terbenzimidazoles exhibited similar cytotoxicity against variants of human tumor cells that either overexpress MDR1 or are camptothecin-resistant.