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Synthesis, Spectroscopic Identification and Molecular Docking of Certain N-(2-{[2-(1H-Indol-2-ylcarbonyl) Hydrazinyl](oxo)Acetylphenyl)Acetamides and N-[2-(2-{[2-(Acetylamino)Phenyl](oxo)Acetylhydrazinyl)-2-Oxoethyl]-1H-Indole-2-Carboxamides: New Antimicrobial Agents.

ABSTRACT: N-(2-{[2-(1H-Indol-2-ylcarbonyl)hydrazinyl](oxo)acetyl}phenyl)acetamides (5a?h) and N-[2-(2-{[2-(acetylamino)phenyl](oxo)acetyl}hydrazinyl)-2-oxoethyl]-1H-indole-2-carboxamides (5i?l) were synthesized and characterized with different analytical tools. N-Acetylisatines 4a?d were subjected to ring opening at their C2 carbons with the aid of different indole-bearing hydrazides 3a,b and 7 to afford the respective glyoxylamides 5a?l. The antimicrobial activity of the target compounds 5a?l was assessed with the aid of Diameter of the Inhibition Zone (DIZ) and Minimum Inhibitory Concentration (MIC) assays against a panel of Gram-positive and Gram-negative bacteria and certain fungal strains. The antimicrobial screening revealed that Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, and Candida albicans are the most sensitive microorganisms towards the synthesized compounds 5a?l. In addition, compounds 5c and 5h emerged as the most active congeners towards Staphylococcus aureus and Candida albicans, respectively. Molecular docking studies revealed the possible binding mode of compounds 5c and 5h to their target proteins.

SUBMITTER: Almutairi MS

PROVIDER: S-EPMC6102541 | biostudies-literature | 2018 Apr

REPOSITORIES: biostudies-literature

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Synthesis, Spectroscopic Identification and Molecular Docking of Certain N-(2-{[2-(1H-Indol-2-ylcarbonyl) Hydrazinyl](oxo)Acetylphenyl)Acetamides and N-[2-(2-{[2-(Acetylamino)Phenyl](oxo)Acetylhydrazinyl)-2-Oxoethyl]-1H-Indole-2-Carboxamides: New Antimicrobial Agents.

Almutairi Maha S MS Zakaria Azza S AS Al-Wabli Reem I RI Joe I Hubert IH Abdelhameed Ali S AS Attia Mohamed I MI

Molecules (Basel, Switzerland) 20180429 5

N-(2-{[2-(1H-Indol-2-ylcarbonyl)hydrazinyl](oxo)acetyl}phenyl)acetamides (5a⁻h) and N-[2-(2-{[2-(acetylamino)phenyl](oxo)acetyl}hydrazinyl)-2-oxoethyl]-1H-indole-2-carboxamides (5i⁻l) were synthesized and characterized with different analytical tools. N-Acetylisatines 4a⁻d were subjected to ring opening at their C2 carbons with the aid of different indole-bearing hydrazides 3a,b and 7 to afford the respective glyoxylamides ...[more]

PMID: 29710842

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Project description:Severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2) is the causative agent of Coronavirus Disease 2019 (COVID-19) pandemic. Despite intensive and global efforts to discover and develop novel antiviral therapies, only Remdesivir has been approved as a treatment for COVID-19. Therefore, effective antiviral therapeutics are still urgently needed to combat and halt the pandemic. Viral RNA-dependent RNA polymerase (RdRp) of SARS-CoV-2 demonstrates high potential as a reliable target for the development of antivirals. We previously developed a cell-based assay to assess the efficiency of compounds that target SARS-CoV-2 RdRp, as well as their tolerance to viral exoribonuclease-mediated proof-reading. In our previous study, we discovered that 2-((1H-indol-3-yl)thio)-N-phenyl-acetamides specifically targets the RdRp of both respiratory syncytial virus (RSV) and influenza A virus. Thus, we hypothesize that 2-((1H-indol-3-yl)thio)-N-phenyl-acetamides may also have the ability to inhibit SARS-CoV-2 replication by targeting its RdRp activity. In this research, we test a compound library containing 103 of 2-((1H-indol-3-yl)thio)-N-phenyl-acetamides against SARS-CoV-2 RdRp, using our cell-based assay. Among these compounds, the top five candidates strongly inhibit SARS-CoV-2 RdRp activity while exhibiting low cytotoxicity and resistance to viral exoribonuclease. Compound 6-72-2a is the most promising candidate with the lowest EC50 value of 1.41 μM and highest selectivity index (CC50/EC50) (above 70.92). Furthermore, our data suggests that 4-46b and 6-72-2a also inhibit the replication of HCoV-OC43 and HCoV-NL63 virus in a dose-dependent manner. Compounds 4-46b and 6-72-2a exhibit EC50 values of 1.13 μM and 0.94 μM, respectively, on HCoV-OC43 viral replication. However, higher concentrations of these compounds are needed to effectively block HCoV-NL63 replication. Together, our findings successfully identified 4-46b and 6-72-2a as promising inhibitors against SARS-CoV-2 RdRp.

Dataset Information

Synthesis, Spectroscopic Identification and Molecular Docking of Certain N-(2-{[2-(1H-Indol-2-ylcarbonyl) Hydrazinyl](oxo)Acetylphenyl)Acetamides and N-[2-(2-{[2-(Acetylamino)Phenyl](oxo)Acetylhydrazinyl)-2-Oxoethyl]-1H-Indole-2-Carboxamides: New Antimicrobial Agents.

Publications

Synthesis, Spectroscopic Identification and Molecular Docking of Certain <i>N</i>-(2-{[2-(1<i>H</i>-Indol-2-ylcarbonyl) Hydrazinyl](oxo)Acetylphenyl)Acetamides and <i>N</i>-[2-(2-{[2-(Acetylamino)Phenyl](oxo)Acetylhydrazinyl)-2-Oxoethyl]-1<i>H</i>-Indole-2-Carboxamides: New Antimicrobial Agents.

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