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RESEARCH ARTICLE

Synthesis and Biological Evaluation of Macrocyclized Betulin Derivatives as a Novel Class of Anti-HIV-1 Maturation Inhibitors

Jun Tang1 , * Open Modal Stacey A. Jones1 Jerry L. Jeffery1 Sonia R. Miranda1 Cristin M. Galardi1 David M. Irlbeck1 Kevin W. Brown1 Charlene B. McDanal1 Nianhe Han2 Daxin Gao2 Yongyong Wu2 Bin Shen2 Chunyu Liu2 Caiming Xi2 Heping Yang2 Rui Li2 Yajun Yu2 Yufei Sun2 Zhimin Jin2 Erjuan Wang2 Brian A. Johns1 Authors Info & Affiliations
The Open Medicinal Chemistry Journal • 3 Sept 2014 • RESEARCH ARTICLE • DOI: 10.2174/1874104501408010023

Abstract

A macrocycle provides diverse functionality and stereochemical complexity in a conformationally preorganized ring structure, and it occupies a unique chemical space in drug discovery. However, the synthetic challenge to access this structural class is high and hinders the exploration of macrocycles. In this study, efficient synthetic routes to macrocyclized betulin derivatives have been established. The macrocycle containing compounds showed equal potency compared to bevirimat in multiple HIV-1 antiviral assays. The synthesis and biological evaluation of this novel series of HIV-1 maturation inhibitors will be discussed.

Keywords: Betulin derivative, HIV, macrocyclization, maturation inhibitor.
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