155579-36-5

Upstream product

• 371-40-4 4-fluoroaniline 
• 499983-03-8 C₁₁H₈FN₅ 
• 129694-52-6 ethyl (Z)-N-(2-amino-1,2-dicyanovinyl)formimidate 
• 129694-52-6 ethyl (Z)-N-(2-amino-1,2-dicyanovinyl)formamidate 
• 155579-21-8 N-((Z)-2-Amino-1,2-dicyano-vinyl)-N'-(4-fluoro-phenyl)-formamidine 

Downstream Products

• 1380583-84-5 4-[5-amino-1-(4-fluorophenyl)-1H-imidazol-4-yl]-5-imino-2-oxo-2,5-dihydro-1H-pyrrole-3-carbonitrile 
• 1380583-91-4 3-(4-fluorophenyl)-8-oxo-7,8-dihydro-3H-imidazo[4,5-d]pyrrolo[3,2-f][1,3]diazepine-9-carbonitrile 
• 1354413-80-1 C₂HF₃O₂*C₁₁H₈FN₅ 
• 1354413-99-2 C₂HF₃O₂*C₁₇H₁₆FN₅ 

Relevant academic research and scientific papers

Anticancer potential of some imidazole and fused imidazole derivatives: Exploring the mechanism: Via epidermal growth factor receptor (EGFR) inhibition

Imidazole-based epidermal growth factor receptor (EGFR) inhibitors were computationally designed and synthesized. All the compounds were assessed for their anti-proliferative activity against five cancer cell lines, viz., MDA-MB-231 (breast), T47D (breast) and MCF-7 (breast), A549 (lung) and HT-29 (colorectal). Compounds 2c and 2d emerged as better anticancer molecules with no toxicity towards normal cells. 2c and 2d inhibited EGFR enzymatic activity in vitro with IC50 values of 617.33 ± 0.04 nM and 710 ± 0.05 nM, respectively. In order to further improve the potency, we explored an unoccupied area of the ATP binding domain of EGFR and analysed an in silico interaction model of 2c and 2d-EGFR complexes that guided and allowed substitution of the 4-fluorophenyl ring (2c and 2d) with 4-(4-methylpiperazinyl)-3-nitrophenyl at the N-9 position, resulting in compound 3c with a better binding score and potent EGFR inhibitory activity (IC50: 236.38 ± 0.04 nM), which was comparable to the positive control erlotinib (239.91 ± 0.05 nM). 3c exhibited a great improvement in anticancer potency with inhibition of cell growth of all cancer cell lines at very low micromolar concentrations (IC50 = 1.98 to 4.07 μM). Further investigation revealed that 3c also induced an increase in ROS levels in cancer cells in a mitochondrial-independent manner and halted the cell cycle at the sub-G1 phase.

A Facile Synthesis of 5-Amino-4-cyano-1-arylimidazoles and 5-Amino-1-aryl-4-(cyanoformimidoyl)-1H-imidazoles from N-Aryl-N'-formamidines

Starting from readily available ethyl (Z)-N-(2-amino-1,2-dicyanovinyl)formimidate, N-aryl-N'-formamidines (2) can be prepared in good yields by reaction with aromatic amines at room temperature in the presence of an acid catalyst