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. 2024 Aug 14;9(34):36671-36681.
doi: 10.1021/acsomega.4c05046. eCollection 2024 Aug 27.

Design, Synthesis, and Antiviral and Fungicidal Activities of 4-Oxo-4 H-quinolin-1-yl Acylhydrazone Derivatives

Peipei Cui  1 , Kaisi Liu  2 , Zhaokai Yang  3 , Ping Sun  3 , Yanan Meng  2 , Qilong Yang  2 , Xinyang Wu  2 , Yongkang Lv  2 , Yan Yang  2 , Jian Wu  3
Affiliations

Design, Synthesis, and Antiviral and Fungicidal Activities of 4-Oxo-4 H-quinolin-1-yl Acylhydrazone Derivatives

Peipei Cui et al. ACS Omega. .

Abstract

To discover novel antiviral agents, based on the high antiviral activity of (4-oxo-4H-quinolin-1-yl)-acetic acid hydrazide (C), a series of 4-oxo-4H-quinoline acylhydrazone derivatives were designed, synthesized, and first evaluated for their antiviral and fungicidal activities. Most acylhydrazone derivatives exhibited moderate to good antiviral activities in vivo. The inactive, curative, and protective activities of compounds 4 (51.2, 47.6, and 46.3%), 11 (49.6, 43.0, and 45.2% at 500 mg/L), and 17 (47.1, 49.2, and 44.1%) were higher than those of ribavirin (39.2, 38.0, and 40.8%) at 500 mg/L. Molecular docking showed that compound 4 exhibited a stronger affinity to TMV coat protein (TMV-CP) than ribavirin, with a binding energy (-6.89 kcal/mol) slightly lower than that of ribavirin (-6.08 kcal/mol). Microscale thermophoresis showed that compound 4 (K d = 0.142 ± 0.060 μM) exhibited a strong binding ability to TMV-CP, superior to that of ribavirin (K d = 0.512 ± 0.257 μM). The results of transmission electron microscopy showed that compound 4 hindered the self-assembly and growth of TMV. The antifungal activities of most compounds were moderate at 50 mg/L, among which compounds 12 and 21 exhibited a 72.1 and 76.5% inhibitory rate against Physalospora piricola, respectively. Meanwhile, compound 16 exhibited a 60% inhibitory rate against Cercospora arachidicola Hori at 50 mg/L.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Natural products and drugs containing a quinoline or acylhydrazone structure.
Figure 2
Figure 2
Design of target compounds.
Figure 3
Figure 3
Synthesis of 4-oxo-4H-quinolin-1-yl acylhydrazone.
Figure 4
Figure 4
Structure of compound 2.
Figure 5
Figure 5
Variable-temperature 1H NMR of compound 2 in DMSO-d6.
Figure 6
Figure 6
TEM images of TMV particles at 200 nm: (A) blank control, (B) compound 4, and (C) ribavirin.
Figure 7
Figure 7
Molecular docking diagrams of ribavirin with TMV-CP (A,C) and compound 4 with TMV-CP (B,D).
Figure 8
Figure 8
Microscale thermophoresis results for compounds 4 (A) and ribavirin (B) with TMV-CP.
See this image and copyright information in PMC

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