HIV-1 integrase is essential for replication of the virus and would be an ideal target of inhibition of its replication pathway. Quinoline-based inhibitors have shown allosteric forms of inhibition of HIV-1 integrase and have proven to be an effective antiretroviral compound by inhibiting replication. These heterocyclic compounds are synthesized in an eight-step sequence from commercially available 4-hydroxy-2-methylquinoline. A palladium-catalyzed Suzuki coupling reaction is the key step, allowing us to introduce diversity using various para-substituted boronic acids. This poster will focus on the synthetic route used to make these compounds and the challenges that occurred during scale-up and during purification of the late stage intermediates. The efficacy of the substituted quinolines to inhibit HIV-1 integrase will also be discussed.

Development of a synthetic strategy for the preparation of various para-functionalized aromatic substituents on a tri-substituted quinoline as drug candidates for HIV-1 integrase inhibition

255th National Meeting (2018)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.