Abstract
Efficient and versatile synthetic methodologies are reported for the preparation of products that are suitable candidates to be used as surfactants, gelators for hydroxylic solvents or metal cation ligands, with potential use in several fields including biomedical applications. The common structural feature of all the synthesized products is the presence of a cis or trans-1,2- or cis-1,3-difunctionalized cyclobutane ring. In the two first cases, the key intermediates including enantiomerically pure 1,3-diamines and 1,3-amino alcohols have been prepared from β-amino acid derivatives obtained, in turn, from a chiral half-ester. This compound is also precursor of γ-amino esters. Furthermore, two kind of polydentate ligands have also been synthesized from a symmetric 1,5-diamine obtained from norpinic acid, which was easily prepared from commercial verbenone.
Highlights
Search for new molecules with suitable properties for biological purposes needs a rational synthetic design involving stereo- and chemoselective methodologies
We describe the utilization of cis- and trans-cyclobutane β-amino acids (β-CBAA) [30] in the stereoselective synthesis of novel chiral cationic surfactants and low-molecular-weight gelators (LMWG)
We showed the suitability of several cyclobutane scaffolds for the preparation of different families of products with potential usefulness in the fields of surfactants, gelators and metal cation ligands
Summary
Search for new molecules with suitable properties for biological purposes needs a rational synthetic design involving stereo- and chemoselective methodologies. Amphiphiles are interesting and versatile compounds with usefulness in different fields. They can be classified in different families regarding their structure. Depending on the nature of the latter, they are classified as cationic, anionic or non-ionic amphiphiles [1]. They present a great potential for biomedical applications in targeted drug delivery systems (DDS) [1] and as non-viral vectors for gene therapy [2]. Cationic surfactants are especially interesting due to the fact of their properties that make them suitable to interact with DNA. Controlled DNA compaction and neutralization of their negatively charged phosphate groups is crucial to transfect into cells avoiding repulsive interactions with phospholipids in the cell membrane [3]
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