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

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 cry...

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Bibliographic Details
Published in:Crystals (Basel) 2019-08, Vol.9 (8), p.379
Main Authors: Ivashchenko, Aleksandr V., Mitkin, Oleg D., Kravchenko, Dmitry V., Kuznetsova, Irina V., Kovalenko, Sergiy M., Bunyatyan, Natalya D., Langer, Thierry
Format: Article
Language:English
Subjects:
1H-indole
3,5-dihydro-4H-pyrimido[5,4-b]indol-4-one
Acetonitrile
Biological activity
Chemical bonds
Crystal structure
Crystallization
Cytotoxicity
Drugs
HBV
Hepatitis B
Hirshfeld surface analysis
hydrogen bond
Hydrogen bonds
Infections
Inhibitors
Ligands
Molecular docking
molecular docking study
Molecular structure
pharmaceutical crystals
pyrimidin-4(3H)-one
Single crystals
Surface analysis (chemical)
Unit cell
Viral infections
X ray analysis
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Summary: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).
ISSN:2073-4352
2073-4352
DOI:10.3390/cryst9080379