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Synthesis, Single Crystal X-Ray Analysis, Prediction and Study of Pharmacological Activity of 4-(1H-Benzo[d]imidazol-2-yl)-1-Phenyl-1H-1,2,3-triazol-5-Amine and Its Solvates

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ChemRar Research and Development Institute, Innovation Center Skolkovo territory, 7 Nobel st., Moscow 143026, Russia
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Chemical Diversity Research Institute, 2A Rabochaya st., Khimki, Moscow Region 141400, Russia
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Sechenov First Moscow State Medical University of the Ministry of Healthcare of the Russian Federation (Sechenov University), 8 Trubeckaya st., Moscow 119991, Russia
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Federal State Budgetary Institution “Scientific Centre for Expert Evaluation of Medicinal Products” of the Ministry of Health of the Russian Federation, Petrovsky boulevard 8, bld. 2, Moscow 127051, Russia
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State Scientific Institution “Institute for Single Crystals” of the National Academy of Sciences of Ukraine, 61001 Kharkov, Ukraine
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V.N.Karazin Kharkiv National University, 4 Svobody sq., 61077 Kharkiv, Ukraine
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Department of Pharmaceutical Chemistry, University of Vienna, Althanstraße 14, A-1090 Vienna, Austria
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Author to whom correspondence should be addressed.
Crystals 2019, 9(12), 644; https://doi.org/10.3390/cryst9120644
Received: 15 November 2019 / Revised: 29 November 2019 / Accepted: 4 December 2019 / Published: 5 December 2019
(This article belongs to the Special Issue Pharmaceutical Crystals and Its Application)
A method for the synthesis of 4- (1H-benzo[d]imidazole-2-yl)-1-phenyl-1H-1,2,3-triazole-5-amine was developed, and the electronic and spatial structure of this molecule was studied theoretically and experimentally. The study of interaction energies between molecules by quantum-chemical calculations allows us to recognize different levels of crystal structure organization and describe the interaction types causing their formation. The classic N-H…N and C-H…N hydrogen bonds play the main role in all the studied crystals forming the primary basic structural motif. Their role is comparable with the role of the stacking interactions. The molecular docking study predicted that the studied compound may exhibit anti-hepatitis B activity, and experimental in vitro studies confirmed that it is a potent HBV inhibitor with IC50 in a low micromolar range. View Full-Text
Keywords: pharmaceutical crystals; benzimidazole; crystal structure; topology of interactions; 4-(1H-benzo[d]imidazol-2-yl)-1-phenyl-1H-1,2,3-triazol-5-amine; 1,2,3-triazole; hydrogen bond pharmaceutical crystals; benzimidazole; crystal structure; topology of interactions; 4-(1H-benzo[d]imidazol-2-yl)-1-phenyl-1H-1,2,3-triazol-5-amine; 1,2,3-triazole; hydrogen bond
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Ivachtchenko, A.V.; Mitkin, O.D.; Kravchenko, D.V.; Kovalenko, S.M.; Shishkina, S.V.; Bunyatyan, N.D.; Konovalova, I.S.; Ivanov, V.V.; Konovalova, O.D.; Langer, T. Synthesis, Single Crystal X-Ray Analysis, Prediction and Study of Pharmacological Activity of 4-(1H-Benzo[d]imidazol-2-yl)-1-Phenyl-1H-1,2,3-triazol-5-Amine and Its Solvates. Crystals 2019, 9, 644.

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