Lipophilic aminophosphonates and their calix[4]arene derivatives: Synthesis and membrane transport of biorelevant species

Many new lipophilic alpha -aminophosphonates including macrocyclic (on cali x[4]arene platform) and chiral ones were synthesized by the Kabachnik-Field s reaction. Some of them were examined as carriers for membrane transport o f biorelevant species such as hydroxy, amino acids, and amino alcohols. Tra nsport measurements showed that these compounds exhibited remarkable effici ency and selectivity of the transport of very hydrophilic substances across lipophilic membranes. The structures of alpha -aminophosphonate-substrate complexes were investigated by spectral and theoretical methods. (C) 2000 J ohn Wiley & Sons, Inc.