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Synthesis of fatty acid Schiff base esters as potential antimicrobial and chemotherapeutic agents

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Abstract

Schiff base {4-[(pyridine-3-ylmethylimino)-methyl] phenol} was prepared by reacting 4-hydroxybenzaldehyde with 3-aminomethylpyridine in ethanol for 6 h (85 % yield) followed by their esterification via reaction with fatty acids of varying chain lengths. The structure of these Schiff base esters were elucidated using chromatographic and spectroscopic techniques like GC–MS, 1H NMR, 13C NMR, and ESI–MS. Schiff base esters with shorter chain heptanoic (2a) and decanoic acid (2c) showed good activity against all the tested bacterial and fungal strains. The synthesized esters were also studied for cytotoxicity toward different human tumor cell lines like HeLa, HepG2, A549, MDA-MB-231, and MCF 7 and Neuro2a; however, Schiff base esters with shorter chain (2a, 2b) and medium chain fatty acids (2d, 2i) exhibited good anticancer activity and selectively toward MDA-MB-231 and MCF 7, while long chain fatty acid (2g) Schiff base ester exhibited good anticancer activity selectively toward MDA-MB-231 as compared to the parent molecule, Schiff base (1).

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Scheme 1
Scheme 2

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Acknowledgments

One of the author Y. M. thanks to the Director, Indian Institute of Chemical Technology, Hyderabad, India and thanks to the Head, Centre for Lipid Research, IICT for giving the financial support.

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Correspondence to M. S. L. Karuna.

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Mohini, Y., Prasad, R.B.N., Karuna, M.S.L. et al. Synthesis of fatty acid Schiff base esters as potential antimicrobial and chemotherapeutic agents. Med Chem Res 22, 4360–4366 (2013). https://doi.org/10.1007/s00044-012-0450-y

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