Medicinal Chemistry Research
Ymax = 21.5, Zmin = 12.0, and Zmax = 30.2). The results were
analyzed and visualized by PyMOL. LigPlot+v1.4.5 was
used to depict the 2D interaction diagrams (Wallace et al.
1995).
Fang YL, Xiao MW, Hu AX, Ye J, Lian WW, Liu AL (2016) Design,
synthesis, and evaluation of 3‐((4‐(t‐Butyl)‐2‐(2‐benzylidenehy-
drazinyl)thiazol‐5‐yl)methyl)quinolin‐2(1H)‐ones
aminidase inhibitors. Chinese J Chem 34:403–411
as
neur-
Feng E, Ye DJ, Li J, Zhang DY, Wang JF, Zhao F, Hilgenfeld R,
Zheng M, Jiang H, Liu H (2012) Recent advances in neur-
aminidase inhibitor development as anti-influenza drugs. Chem-
MedChem 7:1527–1536
DFT calculation
Hatakeyama S, Sugaya N, Ito M, Yamazaki M, Ichikawa M, Kimura
K, Kiso M, Shimizu H, Kawakami C, Koike K, Mitamura K,
Kawaoka Y (2007) Emergence of influenza B viruses with
reduced sensitivity to neuraminidase inhibitors. JAMA
297:1435–1442
The DFT calculations of the representative compounds were
performed at the Becke–Lee–Parr hybrid exchange corre-
lation three-parameter functional (B3LYP) level with stan-
dard 6-311G (d, p) basis set (Kohn et al. 1965; Becke 1993;
Lee et al. 1998).
Ison MG (2011) Antivirals and resistance: influenza virus. Curr Opin
Virol 1:563–573
Vibration analysis showed that the optimized structure
was in accordance with the minimum points on the potential
energy surface. All of the convergent precisions were the
system default values, and all the quantum chemical calcu-
lations in this study were performed using the Gaussian 09
program (Frisch et al., Gaussian 09, Revision A.1, Gaussian,
Inc., Wallingford, CT, 2009). The calculated convergence
accuracy is determined by the program default parameter.
Kohn W, Sham LJ, Kohn W, Sham L (1965) Self-consistent equations
including exchange and correlation effects. Phys Rev 140:
A1133–A1138
Krammer F, Palese P (2015) Advances in the development of influ-
enza virus vaccines. Nature Reviews Drug Discovery 14:167–182
Laver WG, Colman PM, Webster RG, Hinshaw VS, Air GM (1984)
Influenza virus neuraminidase with hemagglutinin activity. Vir-
ology 137:314–323
Lee C, Yang W, Parr RG (1998) Development of the Colle-Salvetti
correlation-energy formula into a functional of the electron den-
sity. Phys Rev B: Condens Matter 37:785–789
Acknowledgements This work was financially supported by the
Hunan Provincial Natural Science Foundation of China (No.
2019JJ40030). The institute of the Chinese Academy of Medical
Sciences and Peking Union Medical College provided the biological
activity assays.
Liu AL, Cao HP, Du GH (2005) Drug screening for influenza neur-
aminidase inhibitors. Sci China C Life Sci 48:1–5
Liu Y, Zhang L, Gong JZ, Fang H, Liu AL, Du GH, Xu WF (2011)
Design, synthesis, and biological activity of thiazole derivatives
as novel influenza neuraminidase inhibitors. J Enzyme Inhib Med
Chem 19:506–513
Lou Z, Sun Y, Rao Z (2014) Current progress in antiviral strategies.
Trends Pharmacol Sci 35:86–102
Compliance with ethical standards
Mitrasinovic PM (2009) On the structure-based design of novel inhi-
bitors of H5N1 influenza A virus neuraminidase (NA). Biophys
Chem 140:35–38
Conflict of interest The authors declare that they have no conflict of
interest.
Nataraj A, Balachandran V, Karthick T (2013) Molecular structure,
vibrational spectra, first hyperpolarizability and HOMO–LUMO
analysis of p-acetylbenzonitrile using quantum chemical calcu-
lation. J Mol Struct 1038:134–144
Publisher’s note: Springer Nature remains neutral with regard to
jurisdictional claims in published maps and institutional affiliations.
Suvitha A, Periandy S, Boomadevi S, Govindarajan M (2014)
Vibrational frequency analysis, FT-IR, FT-Raman, ab initio, HF
and DFT studies, NBO, HOMO-LUMO and electronic structure
calculations on pycolinaldeh yde oxime. Spectrochim Acta Part A
117:216–224
Takano R, Kiso M, Igarashi M, Le QM, Sekijima M, Ito K, Takada A,
Kawaoka Y (2013) Molecular mechanisms underlying oseltami-
vir resistance mediated by an I117V substitution in the neur-
aminidase of subtype H5N1 avian influenza A viruses. J Infect
Dis 207:89–97
The MIST (Management of Influenza in the Southern Hemisphere
Trialists) Study Group (1998) Randomised trial of efficacy and
safety of inhaled zanamivir in treatment of influenza A and B
virus infections. Lancet 352:1877–1881
Wallace AC, Laskowski RA, Thornton JM (1995) LIGPLOT: a pro-
gram to generate schematic diagrams of protein-ligand interac-
tions. Protein Eng 8:127–134
Wang Z, Sun HY, Yao XY, Li D, Xu L, Li YY, Tian S, Hou TJ (2016)
Comprehensive evaluation of ten docking programs on a diverse
set of protein-ligand complexes: the prediction accuracy of
sampling power and scoring power. Phys Chem Chem Phys
18:12964–12975
Wetherall NT, Trivedi T, Zeller J, Hodges SC, McKimm-Breschkin
JL, Zambon M, Hayden FG (2003) Evaluation of neuraminidase
enzyme assays using different substrates to measure susceptibility
References
Baz M, Abed Y, Boivin G (2007) Characterization of drug–resistant
recombinant influenza A/H1N1 viruses selected in vitro with
peramivir and zanamivir. Antiviral Res 74:159–162
Becke AD (1993) Density-functional thermochemistry. III. The role of
exact exchange. J Chem Phy 98:5648–5652
Chavas LM, Kato R, Suzuki N, Itzstein MV, Mann MC, Thomson RJ,
Dyason JC, Jennifer MB, Fusi P, Tringali C, Venerando B,
Tettamanti G, Monti E, Wakatsuki S (2010) Complexity in
influenza virus targeted drug design: interaction with human
sialidases. J Med Chem 53:2998–3002
Colman PM, Varghese JN, Laver WG (2012) Structure of the catalytic and
antigenic sites in influenza virus neuraminidase. Nature 303:41–44
Dawood FS, Iuliano AD, Reed C, Meltzer MI, Shay DK, Cheng PY,
Bandaranayake D, Breiman RF, Brooks WA, Buchy P, Feikin
DR, Fowler KB, Gordon A, Hien NT, Horby P, Huang QS, Katz
MA, Krishnan A, Lal R, Montgomery JM, Mølbak K, Pebody R,
Presanis AM, Razuri H, Steens A, Tinoco YO, Wallinga J, Yu H,
Vong S, Bresee J (2012) Estimated global mortality associated
with the first 12 months of 2009 pandemic influenza A H1N1
virus circulation: a modelling study. Lancet Infect Dis 12:687–695
Ellebedy AH, Webby RJ (2009) Influenza vaccines. Vaccine 27:
D65–D68