Loading…

Synthesis, structural study and biological activity of new derivatives of chrysin containing a 2-mercaptopyridyl or 5-(trifluoromethyl)-2-mercaptopyridyl fragments

New derivatives of chrysin containing 2-mercaptopyridine (2a–2e) or 5-(trifluoromethyl)-2-mercaptopyridine (3a–3e) moieties were prepared from the reaction between bromides (1a–1e) and 2-mercaptopyridine or 5-(trifluoromethyl)-2-mercaptopyridine, respectively. Their structures were elucidated by NMR...

Full description

Saved in:
Bibliographic Details
Published in:Journal of molecular structure 2016-04, Vol.1110, p.196-207
Main Authors: Valdez-Calderón, Alejandro, González-Montiel, Simplicio, Martínez-Otero, Diego, Martínez-Torres, Ataulfo, Vásquez-Pérez, José Manuel, Molina-Vera, Carlos, Torres-Valencia, J. Martín, Alvarado-Rodríguez, José G., Cruz-Borbolla, Julian
Format: Article
Language:English
Subjects:
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:New derivatives of chrysin containing 2-mercaptopyridine (2a–2e) or 5-(trifluoromethyl)-2-mercaptopyridine (3a–3e) moieties were prepared from the reaction between bromides (1a–1e) and 2-mercaptopyridine or 5-(trifluoromethyl)-2-mercaptopyridine, respectively. Their structures were elucidated by NMR, IR and elemental analysis. The molecular structure of compounds 1a, 1c–1e, 2b–2e and 3a was determined by single-crystal X-ray diffraction studies. All rings in these structures are nearly coplanar and they showed an intramolecular hydrogen bond between the phenolic hydroxyl H atom and the carbonyl O atom that forms a six membered ring. The crystal packing also showed a wide variety of intermolecular contacts such as C–H⋯A, π–π, C–H⋯π and lone pair⋯π interactions which were supported by quantum theory of atoms in molecules (QTAIM), Hirshfeld surface, and fingerprint plot analyses. Biological activity of all compounds was tested in growth assays of the nematode Caenorhabiditis elegans. Compounds 2e, 3b and 3c inhibited larval development. [Display omitted] •New chrysin derivatives containing 2-mercaptopyridine were prepared.•Molecular and crystal structure analyses are presented.•Intermolecular contacts were supported by QTAIM and Hirshfeld surface analyses.•Compounds 2e, 3b and 3c inhibited larval development of Caenorhabiditis elegans.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2016.01.055