Titre : Design, Synthesis and Biomedical Applications of Azabicyclo[X.Y.0]alkanone Amino Acids

Endroit : Pavillon J.-Armand Bombardier, salle 1035 à 11 h 00.

Cette conférence sera prononcée par Monsieur Nagavenkata Durga Prasad Atmuri, étudiant au doctorat, du laboratoire de William Lubell, professeur au Département de chimie de l'Université de Montréal.

Résumé: Electrophilic transannular cyclization of 8-, 9-, and 10-membered macrocyclic dipeptide lactams has been shown to give effective entry to azabicyclo[X.Y.0]alkanone amino acid derivatives possessing 5,5-, 5,6-, 6,5-, 6,4-, 6,6-, and 7,5-fused ring systems. Our presentation describes this synthetic strategy starting from the preparation and coupling of vinyl-, allyl-, homoallyl- and homohomoallylglycine building blocks to prepare dipeptides that undergo ring-closing metathesis furnishing the macrocyclic lactams.  Transannular iodolactamization gave typically azabicyclo[X.Y.0]alkanone possessing iodine on the lactam ring.  X-ray crystallographic and spectroscopic analyses of the 8-, 9- , and 10-member macrocycles, as well as certain bicycle analogs demonstrate their potential to serve as constrained dipeptides that mimic the central residues of ideal β-turn geometry. Moreover, palladium catalyzed arylation of dehydro-indolizidin-2-one analogs has been developed and employed to prepare analogues of prostaglandin F2alpha receptor modulators for examination in myometrial contraction assays as potential agents for delaying preterm birth.

Information supplémentaireAnnonce PDF du séminaire