Synthesis and biological evaluation of fatty imidazolines

Abstract

A series of eight fatty imidazolines were synthesized under microwave-assisted conditions using different fatty acids namely octyl, decyl, dodecyl, tetradecyl and octadecyl, mixed fatty acids prepared from Sterculia foetida (containing cyclopropene-rich fatty acids), coconut (containing medium-chain-rich fatty acids), palm (containing saturated-rich fatty acids) and sunflower (containing unsaturated-rich fatty acids). Coconut, sunflower and non-edible oil S. foetida-based imidazolines were synthesized for the first time. The fatty imidazolines were evaluated for anti-fungal activity and found to be good to excellent (MIC, 4.68–18.75 μg ml−1) against the tested Candida strains as compared with fluconazole (MIC, 16–64 μg ml−1) as standard. The fatty imidazolines also exhibited excellent to moderate anti-bacterial activity (MIC, 4.68–75 μg ml−1) against Staphylococcus aureus MTCC 96, S. aureus MLS 16 MTCC 2940 and Pseudomonas aeruginosa MTCC 2453 as compared with neomycin (MIC, 18.75 μg ml−1) as standard. The cytotoxic evaluation of the imidazolines against different cancer cell lines such as HeLa (Human Cervical Cancer Cell line), A549 (Human Alveolar Adenocarcinoma Cell line), MDA-MB-231& MCF7 (Human Breast Adenocarcinoma Cell line) and Neuro2a (Mouse neuroblastoma cell line) showed excellent cytotoxicity for dodecyl (3b), tetradecyl (3c), octadecyl (3d) and coconut (3f)-based imidazolines. Sunflower-based imidazoline (3g) exhibited good anti-cancer activity towards A549, Neuro2a and palm-based imidazoline (3h) towards HeLa, A549 and MCF-7 cell lines.