Title of article :
(1R,3S)-3-(1H-Benzo[d]imidazol-2-yl)-1,2,2-trimethylcyclopentane-1-carboxylic acid as a new anti-diabetic active pharmaceutical ingredient
Author/Authors :
Kovalenko, Sergiy M. V.N. Karazin Kharkiv National University, Ukraine , Konovalova, Irina S. State Scientific Institution Institute for Single Crystals of the National Academy of Sciences of Ukraine, Ukraine , Merzlikin, Sergiy I. National University of Pharmacy, Ukraine , Chuev, Vladimir P. Federal State Autonomous Educational Institution of Higher Education Belgorod State University, Russian Federation , Kravchenko, Dmitry V. Chemical Diversity Research Institute, Russian Federation
Abstract :
The chiral title compound, C16H20N2O2, which can be used for producing active pharmaceutical ingredients for treatment of type 2 pancreatic diabetes and other pathologies dependent on insulin resistance, was prepared from (1R,3S)-camphoric acid and o-phenylenediamine. It crystallized from an ethanol solution in the chiral monoclinic P21 space group. The five-membered ring adopts a twisted conformation with the methyl-substituted C atoms displaced by −0.273 (5) and 0.407 (5) Å from the mean plane through the other three atoms. In the crystal, molecules are linked by O—H⋯N hydrogen bonds, forming chains along the a-axis direction. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to analyze the intermolecular contacts present in the crystal.
Keywords :
Russian Federation , 1H-benzo[d]imidazol-2-yl-1,2,2-trimethylcyclopentane-carboxylic acid , crystal structure , Hirshfeld surface , active pharmaceutical ingredient , type 2 diabetes , anti-diabetic agents
Journal title :
Acta Crystallographica Section E: Crystallographic Communications
