N-Trifluoroacetylated pyrazolines: Synthesis, characterization and antimicrobial studies

Mohammad Asad; Muhammad Nadeem Arshad; Mohammad Oves; Muhammad Khalid; Salman A Khan; Abdullah M Asiri; Mohd Rehan; Hurija Dzudzevic-Cancar

doi:10.1016/j.bioorg.2020.103842

N-Trifluoroacetylated pyrazolines: Synthesis, characterization and antimicrobial studies

Bioorg Chem. 2020 Jun:99:103842. doi: 10.1016/j.bioorg.2020.103842. Epub 2020 Apr 8.

Authors

Mohammad Asad¹, Muhammad Nadeem Arshad², Mohammad Oves³, Muhammad Khalid⁴, Salman A Khan⁵, Abdullah M Asiri², Mohd Rehan⁶, Hurija Dzudzevic-Cancar⁷

Affiliations

¹ Chemistry Department, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia. Electronic address: drasadamu@gmail.com.
² Chemistry Department, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia; Center of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia.
³ Center of Excellence in Environmental Studies, King Abdul-Aziz University, Jeddah 21589, Saudi Arabia.
⁴ Department of Chemistry, Khwaja Fareed University of Engineering & Information Technology, Rahim Yar Khan 64200, Pakistan.
⁵ Chemistry Department, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia.
⁶ King Fahd Medical Research Center, King Abdulaziz University, Jeddah, Saudi Arabia; Department of Medical Laboratory Technology, Faculty of Applied Medical Sciences, King Abdulaziz University, Jeddah, Saudi Arabia.
⁷ Department of Natural Science in Pharmacy, Faculty of Pharmacy, University of Sarajevo, Zmaja od Bosne 8, 71 000 Sarajevo, Bosnia and Herzegovina.

PMID: 32315898
DOI: 10.1016/j.bioorg.2020.103842

Abstract

A series of N-trifluoroacetyl-2-pyrazolines have been synthesized via cyclization of chalcones in the presence of trifluoroacetic acid and hydrazine as a base. The method used for the preparation of pyrazolines was found to be an efficient one as all of the compounds were obtained in good yield (up to 79%). Various spectroscopic techniques established the structures and additionally corroborated the compounds 2a and 2e by single crystal X-ray. Newly synthesized pyrazolines were investigated for their potential as antimicrobial agents. Compound 2a displayed promising antimicrobial activity against pathogenic Escherichia coli and Pseudomonas aeruginosa. Furthermore, the mechanism of the antimicrobial activity of 2a was demonstrated with the help of scanning electron microscopy (SEM), which revealed complete damage of the bacterial cell membrane, providing dead cell debris in the milieu. The minimum inhibitory concentration (MIC) observed was 79 and 90 µM against E. coli and P. aeruginosa, respectively. Hence, these compounds might be significantly useful in antimicrobial drug development.

Keywords: Antimicrobial activity; Chalcones; Crystal structure; N-Trifluoroacetyl-2-pyrazolines.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / chemical synthesis
Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / pharmacology*
Crystallography, X-Ray
Dose-Response Relationship, Drug
Escherichia coli / drug effects*
Microbial Sensitivity Tests
Models, Molecular
Molecular Structure
Pseudomonas aeruginosa / drug effects*
Pyrazoles / chemical synthesis
Pyrazoles / chemistry
Pyrazoles / pharmacology*
Structure-Activity Relationship

Substances

Anti-Bacterial Agents
Pyrazoles