Jun Tang, Stacey A Jones, Jerry L Jeffery, Sonia R Miranda, Cristin M Galardi, David M Irlbeck, Kevin W Brown, Charlene B McDanal, Nianhe Han, Daxin Gao, Yongyong Wu, Bin Shen, Chunyu Liu, Caiming Xi, Heping Yang, Rui Li, Yajun Yu, Yufei Sun, Zhimin Jin, Erjuan Wang, Brian A Johns
{"title":"Synthesis and Biological Evaluation of Macrocyclized Betulin Derivatives as a Novel Class of Anti-HIV-1 Maturation Inhibitors.","authors":"Jun Tang, Stacey A Jones, Jerry L Jeffery, Sonia R Miranda, Cristin M Galardi, David M Irlbeck, Kevin W Brown, Charlene B McDanal, Nianhe Han, Daxin Gao, Yongyong Wu, Bin Shen, Chunyu Liu, Caiming Xi, Heping Yang, Rui Li, Yajun Yu, Yufei Sun, Zhimin Jin, Erjuan Wang, Brian A Johns","doi":"10.2174/1874104501408010023","DOIUrl":null,"url":null,"abstract":"<p><p>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. </p>","PeriodicalId":39133,"journal":{"name":"Open Medicinal Chemistry Journal","volume":"8 ","pages":"23-7"},"PeriodicalIF":0.0000,"publicationDate":"2014-09-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://ftp.ncbi.nlm.nih.gov/pub/pmc/oa_pdf/13/2e/TOMCJ-8-23.PMC4157350.pdf","citationCount":"20","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Open Medicinal Chemistry Journal","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.2174/1874104501408010023","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2014/1/1 0:00:00","PubModel":"eCollection","JCR":"Q2","JCRName":"Pharmacology, Toxicology and Pharmaceutics","Score":null,"Total":0}
引用次数: 20
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.