Synthesis, antioxidant, antimicrobial and antiviral docking studies of ethyl 2-(2-(arylidene)hydrazinyl)thiazole-4-carboxylates.
Z Naturforsch C J Biosci
; 76(11-12): 467-480, 2021 Nov 25.
Article
in English
| MEDLINE | ID: covidwho-1202282
ABSTRACT
A series of ethyl 2-(2-(arylidene)hydrazinyl)thiazole-4-carboxylates (2a-r) was synthesized in two steps from thiosemicarbazones (1a-r), which were cyclized with ethyl bromopyruvate to ethyl 2-(2-(arylidene)hydrazinyl)thiazole-4-carboxylates (2a-r). The structures of compounds (2a-r) were established by FT-IR, 1H- and 13C-NMR. The structure of compound 2a was confirmed by HRMS. The compounds (2a-r) were then evaluated for their antimicrobial and antioxidant assays. The antioxidant studies revealed, ethyl 2-(2-(4-hydroxy-3-methoxybenzylidene)hydrazinyl)thiazole-4-carboxylate (2g) and ethyl 2-(2-(1-phenylethylidene)hydrazinyl)thiazole-4-carboxylate (2h) as promising antioxidant agents with %FRSA 84.46 ± 0.13 and 74.50 ± 0.37, TAC 269.08 ± 0.92 and 269.11 ± 0.61 and TRP 272.34 ± 0.87 and 231.11 ± 0.67 µg AAE/mg dry weight of compound. Beside bioactivities, density functional theory (DFT) methods were used to study the electronic structure and properties of synthesized compounds (2a-m). The potential of synthesized compounds for possible antiviral targets is also predicted through molecular docking methods. The compounds 2e and 2h showed good binding affinities and inhibition constants to be considered as therapeutic target for Mpro protein of SARS-CoV-2 (COVID-19). The present in-depth analysis of synthesized compounds will put them under the spot light for practical applications as antioxidants and the modification in structural motif may open the way for COVID-19 drug.
Keywords
Full text:
Available
Collection:
International databases
Database:
MEDLINE
Main subject:
Antiviral Agents
/
Thiazoles
/
Viral Matrix Proteins
/
Molecular Docking Simulation
/
Anti-Infective Agents
/
Antioxidants
Type of study:
Experimental Studies
/
Prognostic study
Limits:
Humans
Language:
English
Journal:
Z Naturforsch C J Biosci
Year:
2021
Document Type:
Article
Affiliation country:
Znc-2021-0042
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