title: Electron density of two bioactive oligocyclic indole and oxindole derivatives obtained from low-order X-ray data and invariom application.
abstract: 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.
authors: Freie Universität Berlin, Institut für Chemie und Biochemie- Anorganische Chemie, Fabeckstraße 36a, 14195 Berlin, Germany.
authors: Manuela
authors: M
authors: Weber
authors: Simon
authors: S
authors: Grabowsky
authors: Abhijit
authors: A
authors: Hazra
authors: Subhendu
authors: S
authors: Naskar
authors: Sukdeb
authors: S
authors: Banerjee
authors: Nirup B
authors: NB
authors: Mondal
authors: Peter
authors: P
authors: Luger
mesh_terms: D003080:Cold Temperature; D018360:Crystallography, X-Ray; D004583:Electrons; D006860:Hydrogen Bonding; D007211:Indoles / Q000737:chemistry*; D008968:Molecular Conformation; D000078183:Oxindoles; D011763:Pyrrolizidine Alkaloids / Q000737:chemistry*; D011789:Quantum Theory; D055672:Static Electricity
chemical_list: D007211:Indoles; D000078183:Oxindoles; D011763:Pyrrolizidine Alkaloids; C022960:2-oxindole; C030374:indole