5'-azido-5-bromo-5'-deoxy-2',3'-O-isopropylidene-uridine | 57901-66-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5'-azido-5-bromo-5'-deoxy-2',3'-O-isopropylidene-uridine
• 英文别名: 5'-azido-5'-deoxy-2',3'-O-isopropylidene-5-bromouridine；5'-azido-5-bromo-O^2'_,O3'-isopropylidene-5'-deoxy-uridine；1-[(3aR,4R,6R,6aR)-6-(azidomethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-bromopyrimidine-2,4-dione
• CAS: 57901-66-3
• 化学式: C₁₂H₁₄BrN₅O₅
• 分子量: 388.178
• InChiKey: HBEDCVWQJVGHFK-FDDDBJFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  91.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5'-azido-5-bromo-5'-deoxy-2',3'-O-isopropylidene-uridine 在 盐酸 、 三苯基膦 、 sodium nitrite 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.75h， 生成 5',9-anhydro-2',3'-O-isopropylidene-iso xanthosine
  参考文献：
  名称：

  Synthesis of 5′,9-anhydro-3-(β-d-ribofuranosyl)xanthine, and 3,5′-anhydro-xanthosine as potential anti-hepatitis C virus agents

  摘要：

  5 ',9-Anhydro-3-(beta-(D)-ribofuranosyl)xanthine and 3,5 '-anhydro-xanthosine were prepared as potential anti-hepatitis C virus (HCV) agents from uridine and xanthosine, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.120
• 作为产物：
  描述：

  5'-azido-5'-deoxy-2',3'-O-isopropylideneuridine 在 ammonium cerium(IV) nitrate 、 lithium bromide 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以77%的产率得到5'-azido-5-bromo-5'-deoxy-2',3'-O-isopropylidene-uridine
  参考文献：
  名称：

  Synthesis and Anti-Hcv Activity of N ⁹, 5′-Cyclo-3-(β-D-Ribofuranosyl)-8-Azapurin-2-One Derivatives

  摘要：

  A number of 1- or 6-substituted N-9 ,5'-cyclo-3-(beta-D-ribofuranosyl)-8-azapurin-2-one derivatives were synthesized in multi-step reactions. Their anti-hepatitis C virus activities were evaluated and some structure-activity relationship is discussed.

  DOI：

  10.1080/15257770500265802

文献信息

• Compounds with the bicyclo[4.2.1]nonane system for the treatment of flavivridae infections
  申请人：——

  公开号：US20040082574A1

  公开（公告）日：2004-04-29

  The disclosed invention is a bicyclo[4.2.1]nonane and its pharmaceutically acceptable salt or prodrug, and its composition and method of use to treat Flaviviridae (Hepacivirus, Flavivirus, and Pestivirus) infections in a host, including animals, and especially humans.

  本公开发明涉及一种双环[4.2.1]壬烷及其药用可接受的盐或前药，以及其组合物和治疗宿主（包括动物，特别是人类）的黄病毒科（肝病毒、黄病毒和瘟疫病毒）感染的方法。
• SYNTHESIS AND ANTI-HEPATITIS C VIRUS ACTIVITY OF NUCLEOSIDE DERIVATIVES OF <i>N</i> ³,5′-ANHYDRO-4-(β-D-RIBOFURANOSYL)-8-AZAPURIN-2-ONES
  作者：Abdalla E. A. Hassan、Peiyuan Wang、Tamara R. McBrayer、Phillip M. Tharnish、Lieven J. Stuyver、Raymond F. Schinazi、Michael J. Otto、Kyoichi A. Watanabe

  DOI：10.1081/ncn-200059319

  日期：2005.4.1

  A series of N-3,5'-Anhydro-4-(beta-D-ribofuranosyl)-8-azapurin-2-ones were prepared in multistep reactions from uridine as potential anti-hepatitis C virus (HC V) agents. The synthetic details as well as biological evaluations are discussed.
• COMPOUNDS WITH THE BICYCLO 4.2.1 NONANE SYSTEM FOR THE TREATMENT OF i FLAVIVIRIDAE /i INFECTIONS
  申请人：Pharmasset, Inc.

  公开号：EP1545545A2

  公开（公告）日：2005-06-29
• EP1545545A4
  申请人：——

  公开号：EP1545545A4

  公开（公告）日：2008-09-03
• US8093380B2
  申请人：——

  公开号：US8093380B2

  公开（公告）日：2012-01-10