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Issue 27, 2014
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Experimental and theoretical studies on the effect of the oxo group in 1,4-benzodiazepines

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Abstract

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).

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

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Publication details

The article was received on 26 Feb 2014, accepted on 09 May 2014 and first published on 12 May 2014


Article type: Paper
DOI: 10.1039/C4OB00444B
Citation: Org. Biomol. Chem., 2014,12, 4905-4916
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    Experimental and theoretical studies on the effect of the oxo group in 1,4-benzodiazepines

    P. Pertejo, M. García-Valverde, P. Peña, N. A. Cordero, T. Torroba and A. González-Ortega, Org. Biomol. Chem., 2014, 12, 4905
    DOI: 10.1039/C4OB00444B

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