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-phenyl-enedi-amine. 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, mol-ecules 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 inter-molecular contacts present in the crystal.
Highlights
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
The incidence of diabetes has taken on the character of an epidemic in the world
We have found that the disadvantage of the (Æ) and (-) forms of compound 4 described in the patent of Merzlikin et al (2009) is their poor bioavailability as compared to the (+) form
Summary
According to the forecasts of the World Health Organization, the number of patients with diabetes will double and reach 300 million people by 2025 (Zimmet et al, 2001). In this regard, developing and introducing new antidiabetic drugs is of great importance. The synthesis of (1R,3S)-3-(1Hbenzo[d]imidazol-2-yl)-1,2,2- trimethylcyclopentane-1-carboxylic acid 4 was carried out according to Fig. 2 via cyclocondensation of d-(+)-camphoric anhydride 2 with ophenylenediamine 3 in a mixture of toluene and DMF (383 K) by refluxing for several hours (Fig. 2). It should be noted that during the synthesis, the configuration of the chiral centers did not change and the structure of the title molecule was unambiguously confirmed by X-ray analysis
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