Synthesis of novel pyrimidine thioglycosides as structural analogs of favipiravir (avigan) and their antibird flu virus activity

Abu-Zaied, Mamdouh A.; Elgemeie, Galal H.; Mahmoud, Nashwa

doi:10.1080/15257770.2021.1872794

Cited by 11 publications

(4 citation statements)

References 23 publications

(24 reference statements)

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“…It is worth noticing that joining two or more diverse heterocyclic rings into one structure may bring about new compounds with upgraded bioactivity . As an example, pyridines with the benzothiazole moiety have enhanced antibacterial and antifungal activities. , To achieve this goal, new strategies for synthesizing pyridine-bearing benzothiazole moieties have been generated. − As a continuation of our previous work on the synthesis of bioactive heterocyclic ring systems, − we herein report that the cytotoxic activity of some novel arylpyridines incorporated benzothiazole moieties 8a – h against H5N1, SARS-COV-2 viruses, and their inhibition of SARS-COV-2 main protease (M pro ). Molecular docking studies of more potent main protease inhibitors were also performed to find a potential candidate as antiviral agent toward H5N1 and SARS-CoV-2 viruses.…”

Section: Introductionmentioning

confidence: 77%

Synthesis and Biological Evaluation of Benzothiazolyl-pyridine Hybrids as New Antiviral Agents against H5N1 Bird Flu and SARS-COV-2 Viruses

Metwally,

Elgemeie,

Fahmy

2023

ACS Omega

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A novel series of benzothiazolyl-pyridine hybrids 8a−h and 14a−e were produced from the reaction of enamine derivative 4 with each of the arylcyanoacetamides 5a−h and cyanoacetohydrazides 9a−e. The new products were characterized by spectral techniques (IR, 1 H NMR, 13 C NMR, and MS). Biological evaluation of 8a−h and 14a−e in vitro against H5N1 and SARS-COV-2 viruses showed that several compounds had significant activity. Compounds 8f−h, which contain fluorine atoms, have better activity against H5N1 and anti-SARS-CoV-2 viruses than the other compounds included in this study. Compound 8h has a trifluoromethyl group at position-3 of the phenyl ring and exhibits a high activity against H5N1 virus with 93 and 60% inhibition at concentrations of 0.5 and 0.25 μmol/μL, respectively, among the tested compounds, and it also showed anti-SARS-CoV-2 virus with a half-maximum inhibition rate of 3.669 μM, among the remaining compounds. The mechanism of action of 8f−h, which is expected to be repurposed against COVID-19, was investigated. The results showed that the compounds have virucidal effects at different stages of the three mechanisms of action. Furthermore, compounds 8f−h were found to possess CoV-3CL protease inhibitory activities with IC 50 values of 544.6, 868.2, and 240.6 μg/mL, respectively, compared to IC 50 = 129.8 μg/mL of the standard drug lopinavir. Interestingly, compounds 8f−h also showed high inhibitory activity against the H5N1 virus as well as the SARS-CoV-2 virus. Moreover, compounds 8f−h fit admirably into the active site of the SARS-CoV-2 main protease (PDB ID: 6LU7) using the molecular docking Moe software 2015.10.

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Section: Introductionmentioning

confidence: 77%

Synthesis and Biological Evaluation of Benzothiazolyl-pyridine Hybrids as New Antiviral Agents against H5N1 Bird Flu and SARS-COV-2 Viruses

Metwally,

Elgemeie,

Fahmy

2023

ACS Omega

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“…More potent activities were found for compounds 39 and 40 at 0.25 μM concentration against H5 N1 (83 % and 86 % inhibition) and IC 50 values of 12.16 μM for 39 and 14.9 μM for 40 against SARS‐CoV‐2; These compounds were selective for SARS‐CoV‐2, with SI indices of 28.2 and 26.9, for 39 and 40 respectively. Abu‐Zaied and colleagues also previously developed novel favipiravir (Avigan ® ) pyrimidine thioglycoside analogues [41] active against the avian influenza virus (H5 N1). Compounds 41 , 42 , 43 , 44 and 45 showed inhibitions of 75, 75, 77, 78.83 and 83 %, respectively, at a concentration of 0.25 μM (Figure 18).…”

Section: Resultsmentioning

confidence: 99%

Pharmacological Potential of Pyrmidine Derivatives: A Review With Emphasis on Antiviral Effects and Virtual Screening Against Sars‐Cov‐2 Molecular Targets

et al. 2023

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The importance of R&D of new antivirals has been highly evident with the emergence of the pandemic caused by SARS‐CoV‐2. Pyrimidines are heterocyclic compounds with a broad biological spectrum. In this review we emphasize the antiviral application of pyrimidines. Scientific articles, drug and patent registrations were searched using terms involving antiviral pyrimidines. Between 2012 and 2022, more than 100 articles, which show the broad antiviral spectrum of these compounds, were added in this review. The publications of the last five years were prioritized. Anti‐HIV applications were found, their use more evident within the framework of antivirals; among others found were anti‐influenza, anti‐arboviral, and anti‐hepatitis viruses. The results found in the drug and patent databases corroborate the scenario observed in the analysis of scientific articles and demonstrate the importance of researching pyrimidine compounds in periods of great impact on global health. Additionally, through virtual screening of 119 pyrimidines from an in‐house library, we found seventeen pyrimidines with high binding potential with the Mpro and RdRp proteins of SARS‐CoV‐2. Almost all seventeen compounds showed good pharmacokinetic and toxicological profile, mainly compounds 150 and 151 being considered promising for biological evaluation against SARS‐CoV‐2.

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“…Among series of novel compounds, (7 a-d) have displayed potent to moderate antiviral activity (Scheme 8). [127] El Mansouri et al have reported synthesis and furo[2,3d]pyrimidine-1,3,4-oxadiazole hybrids as antiviral and anticancer agents. They prepared final compounds (65a-d) starting from (58a-d) via Songoashira-heterocyclization in presence of nanostructured palladium pyrophosphate (Na 2 PdP 2 O 7 ).…”

Section: Chemistryselectmentioning

confidence: 99%

“…Among series of novel compounds, ( 7 a – d ) have displayed potent to moderate antiviral activity (Scheme 8). [127] …”

Section: Pyrimidine Analogs As Antiviral Agentsmentioning

confidence: 99%

Synthesis and Antiviral Efficacy of Pyrimidine Analogs Targeting Viral Pathways

Basha¹,

Chandana²

2023

ChemistrySelect

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To date, viruses are known to cause chronic to acute pathogenesis. Nevertheless, antiviral drugs have been known for their medicinal applications for the last few decades to treat infections caused by these pathogens. Despite advancements in the field of vaccination and antiviral drugs, there is a need for a molecule that can eradicate or control viral infection without getting resistance from pathogens will be a real challenge. This review covers possible ways to treat viral infections with pyrimidine and its mimics compared to known antiviral drugs. A comprehensive study of the report accomplished synthetic routes of pyrimidine analogs and their target‐specific antiviral potential. The present review article covers literature from 2018 to 2022.

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Synthesis of novel pyrimidine thioglycosides as structural analogs of favipiravir (avigan) and their antibird flu virus activity

Cited by 11 publications

References 23 publications

Synthesis and Biological Evaluation of Benzothiazolyl-pyridine Hybrids as New Antiviral Agents against H5N1 Bird Flu and SARS-COV-2 Viruses

Synthesis and Biological Evaluation of Benzothiazolyl-pyridine Hybrids as New Antiviral Agents against H5N1 Bird Flu and SARS-COV-2 Viruses

Pharmacological Potential of Pyrmidine Derivatives: A Review With Emphasis on Antiviral Effects and Virtual Screening Against Sars‐Cov‐2 Molecular Targets

Synthesis and Antiviral Efficacy of Pyrimidine Analogs Targeting Viral Pathways

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