Synthesis and antimicrobial activity of 3-(2-N-(aryl,acyl)amino-5-methyl-1,3-thiazol-4-yl)-2H-chromen-2-ones

Authors

DOI:

https://doi.org/10.15587/2519-4852.2020.221701

Keywords:

coumarin, thiazole, antimicrobials, alkyl-group, synthesis

Abstract

The aim of this work is to study methods of 3-(2-N-(aryl,acyl)amino-5-methyl-1,3-thiazol-4-yl)-2H-chromen-2-ones preparation and their antimicrobial activity.

Materials and methods. 1Н NMR spectra were recorded on Varian Mercury-200 (200 MHz), 13C NMR spectra were acquired on Bruker Avance 500 1H NMR (500 MHz) and 13C NMR (125 MHz) in DMSO-d6 and CDCl3. LC-MS analysis of compounds was performed on an Agilent 1100 HPLC instrument with chemical ionization at atmospheric pressure (APCI). The study of antimicrobial activity of compounds was performed by agar well diffusion method. The docking studies were performed using Autodock Vina.

Results and discussion. The interaction of 3-(2-bromopropanoyl)-2H-chromen-2-ones with N-substituted thioureas produced novel derivatives of 3-(2-N-(aryl,acyl)amino-5-methyl-1,3-thiazol-4-yl)chromen-2-ones. The study of antimicrobial activity of the obtained compounds allowed to identify active samples against E. сoli and P. aeruginosa strains. Among the tested compounds, 8-methoxy-3-{2-[(2-methoxyphenyl)amino]-5-methyl-1,3-thiazol-4-yl}-2H-chromen-2-one showed higher activity than the reference drug Streptomycin against E. coli strain. Some compounds showed high activity against P. aeruginosa. Docking studies of the synthesized compounds indicated that they can bind in the active site to bacterial tRNA (guanine37-N1)-methyltransferase.

Conclusions. Novel derivatives of 2H-chromen-2-ones with 2-N-(aryl,acyl)amino-5-methyl-1,3-thiazol moiety at the position 3 were obtained by the Hantzsch thiazole synthesis starting from 3-(2-bromopropanoyl)-2H-chromen-2-ones. Studies of antimicrobial activity allowed to identify new 2H-chromen-2-one derivatives as equipotent antimicrobial agents to the reference drug Streptomycin or even more potent. The docking studies revealed that the synthesized compounds may be inhibitors of tRNA (guanine37-N1)-methyltransferase, which is a crucial enzyme for survival of different bacteria, e.g. P. aeruginosa during stress conditions

Author Biographies

Sergiy Vlasov, National University of Pharmacy Pushkinska str., 53, Kharkiv, Ukraine, 61002

Doctor of Pharmaceutical Sciences, Professor

Department of Organic Chemistry

Sergiy Kovalenko, V. N. Karazin Kharkiv National University Svobody sq., 4, Kharkiv, Ukraine, 61022

Doctor of Chemical Sciences, Professor

Department of Organic Chemistry

Inna Orlenko, National University of Pharmacy Pushkinska str., 53, Kharkiv, Ukraine, 61002

PhD, Associate Professor

Department of Organic Chemistry

Iryna Zhuravel, Kharkiv Medical Academy of Postgraduate Education Amosova str., 58, Kharkiv, Ukraine, 61176

Doctor of Chemical Sciences, Professor, Head of Department

Department of Clinical Biochemistry, Forensic Toxicology and Pharmacy

Konstantin Krolenko, Ryvu Therapeutics S.A. Henryka Leona Sternbacha 2, Kraków, Poland, 30-394

PhD, Scientist II

Chemical department

Vitaliy Vlasov, National University of Pharmacy Pushkinska str., 53, Kharkiv, Ukraine, 61002

PhD, Associate Professor

Department of Educational and Information Technologies

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Published

2020-12-30

How to Cite

Vlasov, S., Kovalenko, S., Orlenko, I., Zhuravel, I., Krolenko, K., & Vlasov, V. (2020). Synthesis and antimicrobial activity of 3-(2-N-(aryl,acyl)amino-5-methyl-1,3-thiazol-4-yl)-2H-chromen-2-ones. ScienceRise: Pharmaceutical Science, (6 (28), 50–55. https://doi.org/10.15587/2519-4852.2020.221701

Issue

No. 6 (28) (2020)

Section

Pharmaceutical Science

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Copyright (c) 2020 Sergiy Vlasov, Sergiy Kovalenko, Inna Orlenko, Iryna Zhuravel, Konstantin Krolenko, Vitaliy Vlasov

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