Synthesis and immunomodulatory activity of novel amino acid analogues of fluoxetine

Abstract

Immunomodulators are assigned as a robust tool for the treatment of various medical conditions like AIDS, cancer and autoimmune diseases. In this work, we have synthesized a series of fluoxetine-based small-molecule immunomodulators. Molecules were synthesized by a convergent strategy, where mitsunobu reaction was conducted to synthesize the common starting material. The novel analogues displayed immunomodulatory potential as indicated by the anti-inflammatory effect derived through the compound’s T cell proliferation inhibitory property. The synthesized novel analogues manifested encouraging biological responses, assure their application as immunomodulators.

GRAPHICAL ABSTRACT

Keywords:

• Fluoxetine
• Mitsunobu reaction
• amino acids
• immunomodulators
• IL-10
• T cell proliferation inhibitors

Acknowledgements

MNT thanks ICMR for the award of Senior Research fellowships (GAP-0806). The authors are very thankful to DBT for funding the research under the budget head GAP 0803. IICT communication number-IICT/Pubs./2022/222. Note: The above work has been filed for patent with title “Synthesis and Biological evaluation of Novel 3-phenyl-3-(aryloxy) propan-1-amines and the process for the preparation thereof” Filing No: 202211060662, Dated: Oct/2022.

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

This work was supported by the Department of Biotechnology, Ministry of Science and Technology Budget Head GAP 0803, Indian Council of Medical Research Budget Head GAP 0806.