Exponential growth of organoboron chemistry in recent years is a testament to the wide range of possible utility for boron containing compounds. Boron possesses unique chemical properties which make it valuable in the search for better pharmaceuticals.  The borinic acid target compounds of this research include a chiral 1,3-azaborine, with nitrogen beta to boron. We are synthesizing novel boronates that are designed as compounds with potential dual-mode, both competitive and associative, inhibitory action of HIV-1 protease. The first known 1,3-azaborine cyclic structure has only been recently elucidated by the Lui group from the University of Oregon.  Due to the specifics of our target compound our synthetic approach differs from the first methods to produce the 1,3-azaborine structure. By incorporating a chiral 1,3-azaborine into a transition state peptide mimic we hope to produce a medicinally useful compound. The cyclic boronates, due to their structural rigidity, are expected to be better inhibitors than their straight chain analogs. These novel structures will also serve to expand molecular diversity and organoboron chemistry.

Towards the synthesis of novel 1,3-azaborines as potential HIV-1 protease inhibitors

245th National Meeting (2013)

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