1123339-22-9Relevant academic research and scientific papers
Experimental and theoretical studies on the effect of the oxo group in 1,4-benzodiazepines
Pertejo, Pablo,Garcia-Valverde, Maria,Pena, Pablo,Cordero, Nicolas A.,Torroba, Tomas,Gonzalez-Ortega, Alfonso
, p. 4905 - 4916 (2014/07/07)
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.
Synthesis of benzodiazepine β-turn mimetics by an Ugi 4CC/Staudinger/aza-wittig sequence. Solving the conformational behavior of the Ugi 4CC adducts
Sanudo, Maria,Garcia-Valverde, Maria,Marcaccini, Stefano,Delgado, Jacinto J.,Rojo, Josefa,Torroba, Tomas
supporting information; experimental part, p. 2189 - 2192 (2009/08/07)
5-Oxobenzo[e][l,4]diazepine-3-carboxamides were synthesized by sequential Ugi reaction-Staudinger/aza-Wittig cyclization. The pseudopeptidic backbone of the new benzodiazepine derivatives superimposed well with type I, I, II, and II β-turn motifs. The intermediate Ugi adducts were characterized as two conformers of the enol form by the correlation between 1H NMR spectra and X-ray diffraction structures of model compounds.
