Electron Density of Two Bioactive Oligocyclic Indole and Oxindole Derivatives Obtained from Low-Order X-Ray Data and Invariom Application

Weber, Manuela; Grabowsky, Simon; Hazra, Abhijit; Naskar, Subhendu; Banerjee, Sukdeb; Mondal, Nirup B.; Luger, Peter (2011). Electron Density of Two Bioactive Oligocyclic Indole and Oxindole Derivatives Obtained from Low-Order X-Ray Data and Invariom Application. Chemistry - an Asian journal, 6(6), pp. 1390-1397. Wiley-VCH 10.1002/asia.201000650

Text 015_Weber2011_ChemAsianJ.pdf - Published Version Restricted to registered users only Available under License Publisher holds Copyright. Download (634kB) | Request a copy

For two indole and oxindole bioactive molecules, low-order room-temperature X-ray data were used to generate aspherical electron density (ED) distributions by application of the invariom formalism. An analysis of the ED using the quantum theory of atoms in molecules (QTAIM) was carried out, which allowed for quantitatively examining bond orders and charge separations in various parts of the molecules. The inspection of electrostatic potentials (ESPs) and Hirshfeld surfaces provided additional information on the intermolecular interactions. Thus, reactive regions of the molecules could be identified, covalent and electrostatic contributions to interactions could be visualized, and the forces causing the crystal packing scheme could be rationalized. As the used invariom formalism needs no extra experimental effort compared to routine X-ray analysis, its wide application is recommended because it delivers information far beyond the normally obtained steric properties. In this way, complementary contributions to drug design can be given as is demonstrated for indoles in this study, which are involved in the metabolism of plants and animals as well as in cancer therapy.

Interest & Impact

Downloads

1 since deposited on 06 Feb 2020
0 in the past 12 months

Citations

5 Citations in Web of Science ®
6 Citations in Scopus

Search

in Google Scholar™

Services

Actions (login required)

Edit item

Actions (login required)

Edit item