Design and synthesis of fatty acid derived 4-methoxybenzylamides as antimicrobial agents

Zubair Rehman Nengroo,Aijaz Ahmad,Adil Tantary,Adil Shafi Ganie,Zeshan Umar Shah

doi:10.1016/j.heliyon.2021.e06842

Abstract

A new series of fatty acid amides viz. N-(4-methoxybenzyl)undec-10-enamide (5), (9Z, 12R)-12-Hydroxy-N-(4-methoxybenzyl)octadec-9-enamide (6) and N-(4-methoxy benzyl)oleamide (7) were synthesized by using a suitable synthetic route involving DCC and DMAP as catalysts. The synthesized compounds were characterized through FTIR, NMR spectroscopy, and mass spectrometry. DNA binding studies through spectroscopy and molecular docking were performed to evaluate the binding mechanism of molecules (5–7) with (ctDNA). The inhibition zone with reference to standards, Minimum Inhibitory Concentration (MIC) and Minimum Killing Concentration (MKC) values were determined to study the in vitro antimicrobial activity for tested compounds. Among all the tested compounds, the compound 6 containing hydroxy group at the fatty acid chain showed most powerful antifungal as well as antibacterial activity.

Highlights

Infection due to microbes has become a serious health hazard and has posed grave threat to health care systems
We found a set of conditions that yields better results and optimum conditions for molar ratio of FA, MBA, DCC, and DMAP were set up
The study revealed the interaction of the compounds 5, 6, and 7 binding modes with Calf thymus DNA (ctDNA) by multispectroscopic techniques and molecular modeling study

Summary

Introduction

Infection due to microbes has become a serious health hazard and has posed grave threat to health care systems. Development of antimicrobial agents to treat various infections is an interesting area of contemporary research. The increased drug resistance in microbes leads to severe implications such as higher mortality and morbidity (Devasia et al, 2006). The enteric bacterial infection is one of the major problems in developing countries: Indian-subcontinent and some tropical parts of South Africa (Zhang et al, 2006). Various synthesized drugs containing an Azole and bile acid derived oxazole functionalities have been used against fungal diseases (Fernandez et al, 2016; Shafiei et al, 2020). Bacterial resistance and drug toxicity are the major drawbacks for the treatment of these infections (Li and Webster, 2018). A huge number of diseases are caused by gram-positive and gram-negative bacteria that results in the damage to host tissue (Ramachandran, 2014)

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