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

Presenter Information

Kristín Sigurjonsson

Document Type

Oral Presentation

Campus where you would like to present

SURC Ballroom C/D

Start Date

16-5-2013

End Date

16-5-2013

Abstract

The considerable growth of organoboron chemistry in recent years has promoted a greater interest in the synthetic utility for boron containing compounds. Boron contains distinct chemical properties such as a dynamic coordinate system which can provide additional binding affinity, making it valuable for developing better pharmaceutical drugs. 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. Our target compounds provide a novel synthetic approach to produce the 1,3-azaborine structure due to the specific nature of the project. By incorporating a chiral type 1,3-azaborine into a transition state peptide mimic, we believe it will produce a medicinally significant compound. Cyclic boronates provide greater structural rigidity which are expected to be improved inhibitors than their straight chain analogs. These novel structures will also serve to expand molecular diversity and organoboron chemistry.

Poster Number

48

Faculty Mentor(s)

Levente Fabry-Azstalos

Additional Mentoring Department

Chemistry

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May 16th, 8:20 AM May 16th, 10:50 AM

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

SURC Ballroom C/D

The considerable growth of organoboron chemistry in recent years has promoted a greater interest in the synthetic utility for boron containing compounds. Boron contains distinct chemical properties such as a dynamic coordinate system which can provide additional binding affinity, making it valuable for developing better pharmaceutical drugs. 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. Our target compounds provide a novel synthetic approach to produce the 1,3-azaborine structure due to the specific nature of the project. By incorporating a chiral type 1,3-azaborine into a transition state peptide mimic, we believe it will produce a medicinally significant compound. Cyclic boronates provide greater structural rigidity which are expected to be improved inhibitors than their straight chain analogs. These novel structures will also serve to expand molecular diversity and organoboron chemistry.