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Correlation between biological activity and energies of electronic transitions in benzodiazepines. negative ion mass spectrometry study of br‐substituted derivatives
Author(s) -
Khvostenko Olga G.,
Yarullina Zemfira Sh.,
Vorob'ev Aleksander S.
Publication year - 1998
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/(sici)1097-0231(19981215)12:23<1839::aid-rcm402>3.0.co;2-3
Subject(s) - chemistry , conformational isomerism , mass spectrometry , molecule , benzodiazepine , ion , resonance (particle physics) , electronic correlation , computational chemistry , analytical chemistry (journal) , atomic physics , organic chemistry , chromatography , biochemistry , physics , receptor
In order to find which of the electron structure features of benzodiazepine molecules control their biological activity, a series of benzodiazepine derivatives was investigated by means of negative ion mass spectrometry with resonance electron capture. The resonance curves for negative ion effective yields are presented. Comparison within a series demonstrates a significant (0.6–1.5 eV) shift of curve maxima towards high electron energies (destabilization) for inactive compounds. It is concluded that the destabilization of resonances reflects an increase in energy of several first electronic transitions in the neutral benzodiazepine molecules, and is related to the second (inactive) conformer, the pseudo‐chair. It is suggested that the energies of the electronic transitions are the sought feature of the electron structure of a benzodiazepine molecule which correlates with its activity, and that the stereospecific structure of the benzodiazepine conformers affect the activity via this feature. Copyright © 1998 John Wiley & Sons, Ltd.