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

被引:2
作者
Ivachtchenko, Alexandre V. [1 ]
Mitkin, Oleg D. [1 ]
Kravchenko, Dmitry V. [2 ]
Kovalenko, Sergiy M. [1 ,3 ,6 ]
Shishkina, Svitlana V. [3 ,6 ]
Bunyatyan, Natalya D. [3 ,4 ]
Konovalova, Irina S. [5 ]
Ivanov, Vladimir V. [6 ]
Konovalova, Olena D. [6 ]
Langer, Thierry [7 ]
机构
[1] Innovat Ctr Skolkovo Terr, ChemRar Res & Dev Inst, 7 Nobel St, Moscow 143026, Russia
[2] Chem Divers Res Inst, 2A Rabochaya St, Chimki 141400, Moscow Region, Russia
[3] Sechenov Univ, Sechenov First Moscow State Med Univ, Minist Healthcare Russian Federat, 8 Trubeckaya St, Moscow 119991, Russia
[4] Minist Hlth Russian Federat, Sci Ctr Expert Evaluat Med Prod, Fed State Budgetary Inst, Petrovsky Blvd 8,Bld 2, Moscow 127051, Russia
[5] Natl Acad Sci Ukraine, State Sci Inst, Inst Single Crystals, UA-61001 Kharkov, Ukraine
[6] Kharkov Natl Univ, 4 Svobody Sq, UA-61077 Kharkov, Ukraine
[7] Univ Vienna, Dept Pharmaceut Chem, Althanstr 14, A-1090 Vienna, Austria
来源
CRYSTALS | 2019年 / 9卷 / 12期
关键词
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; 3-triazole; hydrogen bond; 1,2,3-TRIAZOLES; DERIVATIVES; TOPOLOGY; PATTERNS; DESIGN;
D O I
10.3390/cryst9120644
中图分类号
O7 [晶体学];
学科分类号
0702 ; 070205 ; 0703 ; 080501 ;
摘要
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.
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页数:16
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