Stereocontrolled synthesis and biological activity of two diastereoisomers of the potent HIV-1 protease inhibitor saquinavir.
A general enantioselective synthesis of new syn-hydroxyethylamine isosteres has been developed. The approach, based on the controlled opening of functionalized optically active 2,3-epoxy amines, can be conveniently used for the preparation of new peptidomimetics with various residues. Finally the total synthesis of two diastereoisomer analogues of HIV-Protease inhibitor Saquinavir has been achieved and their biological activity evaluated.
Righi
Giuliana
G
Istituto di Chimica Biomolecolare-Sezione di Roma, c/o Dipartimento di Chimica, Università La Sapienza, p.le A. Moro 5, 00185 Roma, Italy. giuliana.righi@uniroma1.it
Ciambrone
Simona
S
Bonini
Carlo
C
Campaner
Pietro
P
D020650:Combinatorial Chemistry Techniques; D017320:HIV Protease Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015497:HIV-1 / Q000187:drug effects*; D020128:Inhibitory Concentration 50; D018716:Molecular Mimicry; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D019258:Saquinavir / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
D017320:HIV Protease Inhibitors; D010455:Peptides; D019258:Saquinavir