Synthesis of AZTpSpCX2ppSA and AZTpSpCX2ppSAZT: Hydrolysis-Resistant Potential Inhibitors of the AZT Excision Reaction of HIV-1 RT

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• 作者：Qianwei Han ; Stefan G. Sarafianos ; Eddy Arnold ; Michael A. Parniak ; Barbara L. Gaffney ; Roger A. Jones
• 刊名：Organic Letters
• 出版年：2007
• 出版时间：December 6, 2007
• 年：2007
• 卷：9
• 期：25
• 页码：5243 - 5246
• 全文大小：64K
• 年卷期：v.9,no.25(December 6, 2007)
• ISSN：1523-7052

文摘

GR ID=ol7023746n00002>We report an efficient, one-flask route for synthesis of AZTp_Sp_CX2pp_SA and AZTp_Sp_CX2pp_SAZT, where X = H and X = F. This route makes useof the differential susceptibility to oxidation of H-phosphonate mono- and diesters, to allow a series of sequential reactions without requiringisolation of intermediates. These compounds are hydrolysis-resistant versions of the AZTppppA that results from excision of AZT by AZT-resistant HIV reverse transcriptase (RT). This family of compounds may therefore be useful in further study of the AZT excision reaction, aswell as in drug design.