A Feasible Synthesis of (−)‐Menthol‐Amino Acid Conjugates as Potential TRPM8 Agonists

A simple and feasible protocol for synthesizing the menthol‐amino acid conjugates by reacting t ‐Boc‐amino acids with (1 R ,2 S ,5 R )‐(−)‐menthol is reported. The synthesis involved the formation of an ester bond between the protected amino acid and (−)‐menthol using DCC, and DMAP as reagents. The...

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Bibliographic Details
Published in:ChemistrySelect (Weinheim) 2023-11, Vol.8 (42)
Main Authors: Deepalekshmi, P., Mahadevaprasad, B., Apoorva, S. N., Shreya, K., Bettadaiah, B. K.
Format: Article
Language:English
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Summary:A simple and feasible protocol for synthesizing the menthol‐amino acid conjugates by reacting t ‐Boc‐amino acids with (1 R ,2 S ,5 R )‐(−)‐menthol is reported. The synthesis involved the formation of an ester bond between the protected amino acid and (−)‐menthol using DCC, and DMAP as reagents. The t ‐Boc‐menthol conjugates are deprotected using TFA in DCM to afford the menthol‐amino acid conjugates in excellent yield (>85 %). (−)‐Menthol possesses therapeutic properties, while amino acids are known for their diverse chemical functionalities and biological activities, making them a promising platform for designing TRPM8 agonists. By combining the unique characteristics of (−)‐menthol and amino acids, this conjugation approach can enhance TRPM8 agonistic activity. The synthesized conjugates are characterized through various spectroscopic techniques.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.202303267