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Review
. 2023 Aug 28;15(9):1826.
doi: 10.3390/v15091826.

Structural and Synthetic Aspects of Small Ring Oxa- and Aza-Heterocyclic Ring Systems as Antiviral Activities

Sibasish Manna  1 , Koushik Das  1 , Sougata Santra  2 , Emily V Nosova  2   3 , Grigory V Zyryanov  2   3 , Sandipan Halder  1
Affiliations
Review

Structural and Synthetic Aspects of Small Ring Oxa- and Aza-Heterocyclic Ring Systems as Antiviral Activities

Sibasish Manna et al. Viruses. .

Abstract

Antiviral properties of different oxa- and aza-heterocycles are identified and properly correlated with their structural features and discussed in this review article. The primary objective is to explore the activity of such ring systems as antiviral agents, as well as their synthetic routes and biological significance. Eventually, the structure-activity relationship (SAR) of the heterocyclic compounds, along with their salient characteristics are exhibited to build a suitable platform for medicinal chemists and biotechnologists. The synergistic conclusions are extremely important for the introduction of a newer tool for the future drug discovery program.

Keywords: Structure Activity Relationship (SAR); antiviral agents; heterocycles; natural products; synthetic methods.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Global mortality rate per year due to different viral infections [13].
Figure 2
Figure 2
First FDA-approved antiviral drug Idoxuridine.
Figure 3
Figure 3
Representative examples of antiviral drug candidates.
Figure 3
Figure 3
Representative examples of antiviral drug candidates.
Figure 4
Figure 4
Representative nucleoside drugs.
Figure 4
Figure 4
Representative nucleoside drugs.
Figure 5
Figure 5
Representative natural products having antiviral activities.
Figure 6
Figure 6
Chemical structure of darunavir (1).
Figure 7
Figure 7
The interaction of darunavir with HIV-1 PR.
Scheme 1
Scheme 1
Synthesis of darunavir.
Figure 8
Figure 8
Fluoroquinolone-isatin-thiosemicarbazone hybrid (2), a potential anti-HIV agent.
Scheme 2
Scheme 2
Synthesis of fluoroquinolone-isatin-thiosemicarbazone hybrid.
Figure 9
Figure 9
Chemical structure of amprenavir (3).
Figure 10
Figure 10
H-bonds and water-mediated interactions formed by amprenavir with the active site.
Scheme 3
Scheme 3
Synthesis of amprenavir.
Figure 11
Figure 11
Chemical structure of asunaprevir (4).
Figure 12
Figure 12
Structure of HCV NS3/4A protease in complex with asunaprevir.
Scheme 4
Scheme 4
Synthesis of anti-HCV agent asunaprevir.
Figure 13
Figure 13
3-(1,2,4-oxadiazole)-quinolone derivative (5) with anti-HCV activities.
Scheme 5
Scheme 5
Synthesis of 3-(1,2,4-oxadiazole)-quinolone derivatives.
Figure 14
Figure 14
Chemical structure of grazoprevir (7).
Scheme 6
Scheme 6
Synthesis of grazoprevir.
Figure 15
Figure 15
Chemical structure of lamivudine (6).
Scheme 7
Scheme 7
Synthesis of anti-HBV agent lamivudine.
Figure 16
Figure 16
Chemical structure of entecavir (28).
Figure 17
Figure 17
Entecavir triphosphate docking with HBVpol.
Scheme 8
Scheme 8
Synthesis of entecavir.
Scheme 9
Scheme 9
Synthesis of dehydro-andrographolide (35) and andrographolide (36) derivatives.
Figure 18
Figure 18
Chemical structure of ribavirin (10).
Scheme 10
Scheme 10
Synthesis of ribavirin.
Figure 19
Figure 19
Chemical structure of iso-Valganciclovir hydrochloride (21).
Scheme 11
Scheme 11
Synthesis of iso-valganciclovir hydrochloride.
Figure 20
Figure 20
Chemical structure of ganciclovir (22).
Scheme 12
Scheme 12
Synthesis of Ganciclovir.
Figure 21
Figure 21
1,2,4-triazol-quinoxalin derivative (19), a new anti-human-cytomegalovirus (HCMV) agent.
Scheme 13
Scheme 13
Synthesis of 1,2,4-triazol-quinoxalin derivative.
Figure 22
Figure 22
Anti Ebola agent remdesivir (15).
Scheme 14
Scheme 14
Synthesis of remdesivir.
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