Synthesis, X-ray crystal structure, Hirshfeld surface analysis, and molecular docking study of novel inhibitor of hepatitis B: methyl 4-fluoro-3-(morpholinosulfonyl)benzo[b]thiophene-2-carboxylate
Alexandre V. Ivachtchenko,
Oleg D. Mitkin,
Dmitry V. Kravchenko,
Sergiy M. Kovalenko,
Svitlana V. Shishkina,
Natalya D. Bunyatyan,
Irina S. Konovalova,
Irina G. Dmitrieva,
Vladimir V. Ivanov,
Thierry Langer
Affiliations
Alexandre V. Ivachtchenko
ChemRar Research and Development Institute, 7 Nobel st., Innovation Center Skolkovo Territory, Moscow, 143026, Russia
Oleg D. Mitkin
ChemRar Research and Development Institute, 7 Nobel st., Innovation Center Skolkovo Territory, Moscow, 143026, Russia; Corresponding author.
Dmitry V. Kravchenko
Chemical Diversity Research Institute, 2A Rabochaya st., Khimki, Moscow Region, 141400, Russia
Sergiy M. Kovalenko
ChemRar Research and Development Institute, 7 Nobel st., Innovation Center Skolkovo Territory, Moscow, 143026, Russia; Federal State Autonomous Educational Institution of Higher Education I.M. Sechenov First Moscow State Medical University of the Ministry of Healthcare of the Russian Federation (Sechenovskiy University), 8 Trubeckaya st., Moscow, 119991, Russia; V.N.Karazin Kharkiv National University, 4 Svobody sq., Kharkiv, 61077, Ukraine
Svitlana V. Shishkina
Federal State Autonomous Educational Institution of Higher Education I.M. Sechenov First Moscow State Medical University of the Ministry of Healthcare of the Russian Federation (Sechenovskiy University), 8 Trubeckaya st., Moscow, 119991, Russia; State Scientific Institution “Institute for Single Crystals” of the National Academy of Sciences of Ukraine, 61001, Kharkov, Ukraine; V.N.Karazin Kharkiv National University, 4 Svobody sq., Kharkiv, 61077, Ukraine
Natalya D. Bunyatyan
Federal State Autonomous Educational Institution of Higher Education I.M. Sechenov First Moscow State Medical University of the Ministry of Healthcare of the Russian Federation (Sechenovskiy University), 8 Trubeckaya st., Moscow, 119991, Russia; 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
Irina S. Konovalova
State Scientific Institution “Institute for Single Crystals” of the National Academy of Sciences of Ukraine, 61001, Kharkov, Ukraine
Irina G. Dmitrieva
Chemical Diversity Research Institute, 2A Rabochaya st., Khimki, Moscow Region, 141400, Russia
Vladimir V. Ivanov
V.N.Karazin Kharkiv National University, 4 Svobody sq., Kharkiv, 61077, Ukraine
Thierry Langer
Department of Pharmaceutical Chemistry, University of Vienna, Althanstraße 14, A-1090, Vienna, Austria
A method of 4-fluoro-3-(morpholinosulfonyl)benzo[b]thiophene-2-carboxylate synthesis has been developed and the electronic and spatial structure of a new biologically active molecule has been studied both theoretically and experimentally. The title compound was crystallized from acetonitrile and the single crystal X-ray analysis has revealed that it exists in a monoclinic P21/c space group, with one molecule in the asymmetric part of the unit cell. Hirshfeld surface analysis was used to study intermolecular interactions in the crystal. Molecular docking study evaluates the investigated compound as a new potential inhibitor of hepatitis B. Testing for anti-hepatitis B virus activity has shown that this substance demonstrates in vitro nanomolar inhibitory activity against HBV.
