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(1R,3S)-3-(1H-Benzo[d]imidazol-2-yl)-1,2,2-trimethylcyclopentane-1-carboxylic acid as a new anti-diabetic active pharmaceutical ingredient
The chiral title compound, C(16)H(20)N(2)O(2), 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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7472757/ https://www.ncbi.nlm.nih.gov/pubmed/32939290 http://dx.doi.org/10.1107/S2056989020010439 |
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author | Kovalenko, Sergiy M. Konovalova, Irina S. Merzlikin, Sergiy I. Chuev, Vladimir P. Kravchenko, Dmitry V. |
author_facet | Kovalenko, Sergiy M. Konovalova, Irina S. Merzlikin, Sergiy I. Chuev, Vladimir P. Kravchenko, Dmitry V. |
author_sort | Kovalenko, Sergiy M. |
collection | PubMed |
description | The chiral title compound, C(16)H(20)N(2)O(2), 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 P2(1) 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. |
format | Online Article Text |
id | pubmed-7472757 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-74727572020-09-15 (1R,3S)-3-(1H-Benzo[d]imidazol-2-yl)-1,2,2-trimethylcyclopentane-1-carboxylic acid as a new anti-diabetic active pharmaceutical ingredient Kovalenko, Sergiy M. Konovalova, Irina S. Merzlikin, Sergiy I. Chuev, Vladimir P. Kravchenko, Dmitry V. Acta Crystallogr E Crystallogr Commun Research Communications The chiral title compound, C(16)H(20)N(2)O(2), 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 P2(1) 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. International Union of Crystallography 2020-08-04 /pmc/articles/PMC7472757/ /pubmed/32939290 http://dx.doi.org/10.1107/S2056989020010439 Text en © Kovalenko et al. 2020 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Research Communications Kovalenko, Sergiy M. Konovalova, Irina S. Merzlikin, Sergiy I. Chuev, Vladimir P. Kravchenko, Dmitry V. (1R,3S)-3-(1H-Benzo[d]imidazol-2-yl)-1,2,2-trimethylcyclopentane-1-carboxylic acid as a new anti-diabetic active pharmaceutical ingredient |
title | (1R,3S)-3-(1H-Benzo[d]imidazol-2-yl)-1,2,2-trimethylcyclopentane-1-carboxylic acid as a new anti-diabetic active pharmaceutical ingredient |
title_full | (1R,3S)-3-(1H-Benzo[d]imidazol-2-yl)-1,2,2-trimethylcyclopentane-1-carboxylic acid as a new anti-diabetic active pharmaceutical ingredient |
title_fullStr | (1R,3S)-3-(1H-Benzo[d]imidazol-2-yl)-1,2,2-trimethylcyclopentane-1-carboxylic acid as a new anti-diabetic active pharmaceutical ingredient |
title_full_unstemmed | (1R,3S)-3-(1H-Benzo[d]imidazol-2-yl)-1,2,2-trimethylcyclopentane-1-carboxylic acid as a new anti-diabetic active pharmaceutical ingredient |
title_short | (1R,3S)-3-(1H-Benzo[d]imidazol-2-yl)-1,2,2-trimethylcyclopentane-1-carboxylic acid as a new anti-diabetic active pharmaceutical ingredient |
title_sort | (1r,3s)-3-(1h-benzo[d]imidazol-2-yl)-1,2,2-trimethylcyclopentane-1-carboxylic acid as a new anti-diabetic active pharmaceutical ingredient |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7472757/ https://www.ncbi.nlm.nih.gov/pubmed/32939290 http://dx.doi.org/10.1107/S2056989020010439 |
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