Synthesis, Antibacterial and Antitubercular Evaluation of Cardanol and Glycerol‑Based β-Amino Alcohol Derivatives

Bhaskar Reddy Manda ,Adilson Beatriz,Wanderson Romão,Dênis Pires De Lima ,Ana Camila Micheletti ,Heloá Santos ,Narendar R Thatikonda ,Edson A Dos Santos ,Fernando Rogério Pavan ,Maria Rita Marques ,A R Prasad ,Layla R Barbosa ,Valdemar Lacerda ,Carolina Barbosa Ribeiro

doi:10.21577/0103-5053.20170178

Abstract

The synthesis of novel amino alcohol derivatives based on cardanol and glycerol were achieved in good yields and characterized by 1H and 13C NMR (nuclear magnetic resonance) and MS (mass spectrometry). In addition, we evaluated the in vitro antimicrobial activity against Gram-positive (Staphylococcus aureus, standard and clinical strains), Gram-negative (Escherichia coli) and M. tuberculosis bacterial strains. The bioassay results indicated that four compounds showed activity against S. aureus, including the clinical resistant strain, with MIC (minimum inhibitory concentration) ranging from 3.90 to 15.60 µg mL-1 and M. tuberculosis, with MIC90 (minimum inhibitory concentration required to inhibit the growth of 90% of organisms) ranging from 3.18 to 7.36 µg mL-1.

Highlights

The synthesis of fine chemicals from natural renewable resources has received great interest in synthetic community and is becoming a significant and challenging theme for researchers of both the academic and industrial sectors
Solvent was removed in vacuum and the crude compound was purified by column chromatography using 20-50% of EtOAc in hexane as eluent to afford the desired amino alcohol derivative of cardanol
Mycobacterium tuberculosis The antitubercular activity of all compounds was determined through the resazurin microtiter assay (REMA) methodology according to the procedures described by Palomino et al.[59]

Summary

Introduction

The synthesis of fine chemicals from natural renewable resources has received great interest in synthetic community and is becoming a significant and challenging theme for researchers of both the academic and industrial sectors. We report a new strategy for the synthesis of β-amino alcohols by reacting cardanol epoxide with diverse amines (aliphatic/ aromatic) under catalyst-free and mild conditions in which ethanol is used as the reaction medium.

Results

Conclusion