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

ABSTRACT: 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, ¹H NMR, ¹³C 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 IC₅₀ values of 544.6, 868.2, and 240.6 μg/mL, respectively, compared to IC₅₀ = 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.

SUBMITTER: Metwally NH

PROVIDER: S-EPMC10568744 | biostudies-literature | 2023 Oct

REPOSITORIES: biostudies-literature

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

Metwally Nadia Hanafy NH Elgemeie Galal Hamza GH Fahmy Fatma Gomaa FG

ACS omega 20230925 40

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, 1H NMR, 13C NMR, and MS). Biological evaluation of 8a-h and 14a-e in vitro against H5N1 and SARS-COV-2 viruses showed that ...[more]

PMID: 37841136

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Project description:Bacterial infections have attracted the attention of researchers in recent decades, especially due to the special problems they have faced, such as their increasing diversity and resistance to antibiotic treatment. The emergence and development of the SARS-CoV-2 infection stimulated even more research to find new structures with antimicrobial and antiviral properties. Among the heterocyclic compounds with remarkable therapeutic properties, benzimidazoles, and triazoles stand out, possessing antimicrobial, antiviral, antitumor, anti-Alzheimer, anti-inflammatory, analgesic, antidiabetic, or anti-ulcer activities. In addition, the literature of the last decade reports benzimidazole-triazole hybrids with improved biological properties compared to the properties of simple mono-heterocyclic compounds. This review aims to provide an update on the synthesis methods of these hybrids, along with their antimicrobial and antiviral activities, as well as the structure-activity relationship reported in the literature. It was found that the presence of certain groups grafted onto the benzimidazole and/or triazole nuclei (-F, -Cl, -Br, -CF3, -NO2, -CN, -CHO, -OH, OCH3, COOCH3), as well as the presence of some heterocycles (pyridine, pyrimidine, thiazole, indole, isoxazole, thiadiazole, coumarin) increases the antimicrobial activity of benzimidazole-triazole hybrids. Also, the presence of the oxygen or sulfur atom in the bridge connecting the benzimidazole and triazole rings generally increases the antimicrobial activity of the hybrids. The literature mentions only benzimidazole-1,2,3-triazole hybrids with antiviral properties. Both for antimicrobial and antiviral hybrids, the presence of an additional triazole ring increases their biological activity, which is in agreement with the three-dimensional binding mode of compounds. This review summarizes the advances of benzimidazole triazole derivatives as potential antimicrobial and antiviral agents covering articles published from 2000 to 2023.

Dataset Information

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

Publications

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

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