1616366-96-1

Upstream product

• 931-53-3 Cyclohexyl isocyanide 
• 1074-12-0 phenylglyoxal hydrate 
• 552-16-9 ortho-nitrobenzoic acid 
• 100-46-9 benzylamine 

Downstream Products

• 1123339-22-9 N-cyclohexyl-4-benzyl-5-oxo-2-phenyl-3,4-dihydrobenzo[e][1,4]diazepine-3-carboxamide 

Relevant academic research and scientific papers

Experimental and theoretical studies on the effect of the oxo group in 1,4-benzodiazepines

Two families of regioisomeric 1,4-benzodiazepines, 4-benzyl-3H-benzo[e][1, 4]diazepin-5-ones and 4-benzoyl-4,5-dihydro-3H-benzo[e][1,4]diazepines, have been synthesized through a similar Ugi/reduction cyclization sequence. Their conformation and stability depend on the position of the tautomeric imine/enamine equilibrium present in the diazepine nucleus, which in turn depends on the relative position of the carbonyl group adjacent to the nitrogen at the 4-position in the benzodiazepine system. Moreover, the electrophilic center on the imine tautomer is essential for the antitumor activity of some benzodiazepines as a DNA binding position. The mechanism of tautomerization in the presence or absence of the oxo group has been studied computationally using DFT methods (B3LYP/6-31G** level). This journal is the Partner Organisations 2014.