Diane K. Luci

A concise synthesis of an indenopyrrolidine-based dual αvβ3/αvβ5 integrin antagonist

A new class of dual α v β 3 /α v β 5 integrin antagonists containing a central cis-fused cyclopentane ring was identified. Because of its increased structural rigidity, the indenopyrrolidine ring system provides insight intothe active conformation of other α v β 3 ligands. A concise synthesis of the indenopyrrolidine ring system was accomplished by 1,3-dipolar cycloaddition. Individual isomers of the most active compound were separated by chiral HPLC and their biological activities were compared.

The Heck reaction with unprotected allylic amidines and guanidines

The applicability of Heck methodology to the introduction of unprotected amidines and guanidines was investigated. Unprotected guanidine-substituted olefins were coupled to various simple aryl iodides, and this methodology was then applied to a highly functionalized 6-iodoquinazolinone substrate, providing an efficient synthesis of a new class of vitronectin receptor (αVβ3 integrin) antagonists.