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Synthesis, X-Ray Crystal Structure, Hirshfeld Surface Analysis, and Molecular Docking Study of Novel Hepatitis B (HBV) Inhibitor: 8-Fluoro-5-(4-fluorobenzyl)-3-(2-methoxybenzyl)-3,5-dihydro-4H-pyrimido[5,4-b]indol-4-one

1
ChemRar Research and Development Institute, 7 Nobel st., Innovation Center Skolkovo Territory, 143026 Moscow, Russia
2
Chemical Diversity Research Institute, 2A Rabochaya st., Khimki, 141400 Moscow Region, Russia
3
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., 119991 Moscow, Russia
4
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, 127051 Moscow, Russia
5
Department of Pharmaceutical Chemistry, University of Vienna, Althanstraße 14, A-1090 Vienna, Austria
*
Author to whom correspondence should be addressed.
Crystals 2019, 9(8), 379; https://doi.org/10.3390/cryst9080379
Received: 6 June 2019 / Revised: 6 July 2019 / Accepted: 18 July 2019 / Published: 24 July 2019
(This article belongs to the Special Issue Pharmaceutical Crystals)
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Abstract

A method for the synthesis of 8-fluoro-5-(4-fluorobenzyl)-3-(2-methoxybenzyl)-3,5-dihydro-4H-pyrimido[5,4-b]indol-4-one 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/n space group, with one molecule in the asymmetric part of the unit cell, a = 16.366(3) Å, b = 6.0295(14) Å, c = 21.358(4) Å, β = 105.21(2)°, V = 2033.7(7) Å3 and Z = 4. Hirshfeld surface analysis was used to study intermolecular interactions in the crystal. Molecular docking studies have evaluated the investigated compound as a new inhibitor of hepatitis B. Testing for anti-hepatitis B virus activity has shown that this substance has in vitro nanomolar inhibitory activity against Hepatitis B virus (HBV). View Full-Text
Keywords: hepatitis B; HBV; pharmaceutical crystals; 3,5-dihydro-4H-pyrimido[5,4-b]indol-4-one; 1H-indole; pyrimidin-4(3H)-one; hydrogen bond; Hirshfeld surface analysis; molecular docking study hepatitis B; HBV; pharmaceutical crystals; 3,5-dihydro-4H-pyrimido[5,4-b]indol-4-one; 1H-indole; pyrimidin-4(3H)-one; hydrogen bond; Hirshfeld surface analysis; molecular docking study
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Ivashchenko, A.V.; Mitkin, O.D.; Kravchenko, D.V.; Kuznetsova, I.V.; Kovalenko, S.M.; Bunyatyan, N.D.; Langer, T. Synthesis, X-Ray Crystal Structure, Hirshfeld Surface Analysis, and Molecular Docking Study of Novel Hepatitis B (HBV) Inhibitor: 8-Fluoro-5-(4-fluorobenzyl)-3-(2-methoxybenzyl)-3,5-dihydro-4H-pyrimido[5,4-b]indol-4-one. Crystals 2019, 9, 379.

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