Acta Pharm. 50 (2000) 173-184

Synthesis of new adamantane substituted acyclic MDP analogs related to LK 415

UROS URLEB  and  STANISLAV GOBEC 

Faculty of Pharmacy, University of Ljubljana, Ljubljana, Slovenia

The synthesis of different muramyl dipeptide analog LK 415 derivatives as potential immunomodulators is presented. The L-alanine of LK 415 has been replaced by L-proline, L-valine, and by its phosphonic analog methoxy L,D-phosphonoalanine, yielding the LK 415 analogs 5, 7, and 16, respectively. The 2-(ethoxy)acetic acid linker connecting adamantanecarboxamido and dipeptide part of LK 415 has been replaced by both propanoyl and pentanoyl chains, which afforded the adamantlycarboxamidoalkanoyl analogs 10a,b. The w-carboxylic group of LK 415 has been replaced by diethyl phosphonate group, which resulted in analog 13.

Keywords: immunomodulators, muramyl dipeptide, adamantanecarboxamido analogs, phosponate analogs, phosphonamidate analogs