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

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

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)

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Abstract

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

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MDPI and ACS Style

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. https://doi.org/10.3390/cryst9120644

AMA Style

Ivachtchenko AV, Mitkin OD, Kravchenko DV, Kovalenko SM, Shishkina SV, Bunyatyan ND, Konovalova IS, Ivanov VV, Konovalova OD, 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(12):644. https://doi.org/10.3390/cryst9120644

Chicago/Turabian Style

Ivachtchenko, Alexandre V., Oleg D. Mitkin, Dmitry V. Kravchenko, Sergiy M. Kovalenko, Svitlana V. Shishkina, Natalya D. Bunyatyan, Irina S. Konovalova, Vladimir V. Ivanov, Olena D. Konovalova, and Thierry Langer. 2019. "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 9, no. 12: 644. https://doi.org/10.3390/cryst9120644

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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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