1-(3'-Azido-2',3'-dideoxy-α-L-threo-pentofuranosyl)thymine | 132970-02-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(3'-Azido-2',3'-dideoxy-α-L-threo-pentofuranosyl)thymine
• 英文别名: 1-(2,3-Dideoxy-3-azido-α-L-threo-pentafuranosyl)thymine；1-(3-azido-2,3-dideoxy-α-L-threo-pentofuranosyl)thymine；zidovudine；1-[(2R,4S,5R)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione；1-[(2R,4S,5R)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 132970-02-6
• 化学式: C₁₀H₁₃N₅O₄
• 分子量: 267.244
• InChiKey: HBOMLICNUCNMMY-BIIVOSGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  93.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3'-Azido-2',3'-dideoxy-α-L-threo-pentofuranosyl)thymine 、 2-氯-1,3,2-苯并二氧磷杂环己烷-4-酮 生成 1-[(2R,4S,5R)-4-azido-5-[(4-oxo-1,3,2-benzodioxaphosphinin-2-yl)oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  LUDWIG, JANOS;ECKSTEIN, FRITZ, NUCLEOSIDES AND NUCLEOTIDES, 10,(1991) N-3, C. 663-664

  摘要：

  DOI：
• 作为产物：
  描述：

  L-(+)-arabinose 在 吡啶 、 4-二甲氨基吡啶 、 calcium sulfate 、 三甲基氯硅烷 、 叠氮化锂 、 偶氮二异丁腈 、 硫酸 、 四丁基氟化铵 、 三正丁基氢锡 、 sodium methylate 、 四氯化锡 、 溶剂黄146 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 甲醇 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 133.75h， 生成 1-(3'-Azido-2',3'-dideoxy-α-L-threo-pentofuranosyl)thymine
  参考文献：
  名称：

  Synthesis of 1-(3′-Azido-2′,3′-dideoxy-α-L-threo-pentofuranosyl)thymine as a Potential Anti-HIV Agent

  摘要：

  以甲基2,3,5-三-O-苯甲酰-α-L-阿拉伯呋喃糖苷为起始物，描述了AZT的C-4'异构体的多步合成。用2,3,5-三-O-苯甲酰-L-阿拉伯呋喃糖乙酸酯（5）对硅化胸腺嘧啶进行糖苷化反应，在去苯甲酰化后获得α-核苷7。在选择性保护的化合物8的C-2'处去氧化，然后用锂叠氮化物替换3'-甲磺酰基，得到的目标化合物对HIV-1未表现出抗病毒活性。

  DOI：

  10.1055/s-1991-26543

文献信息

• Methods and compositions for the treatment or prevention of human immunodeficiency virus and related conditions using cyclooxygenase-2 selective inhibitors and antiviral agents
  申请人：Maziasz Timothy

  公开号：US20050026902A1

  公开（公告）日：2005-02-03

  The present invention provides compositions and methods for the treatment of human immunodeficiency virus (HIV) infection as well as HIV associated diseases and related disorders. More particularly, the invention provides a combination therapy for the treatment of HIV infection as well as HIV associated diseases and related disorders comprising the administration to a subject of an anti-human immunodeficiency virus agent in combination with a cyclooxygenase-2 selective inhibitor or an isomer or a pharmaceutically acceptable salt, ester, or prodrug thereof.

  本发明提供了治疗人类免疫缺陷病毒（HIV）感染以及HIV相关疾病和相关紊乱的组合物和方法。更具体地说，本发明提供了一种治疗HIV感染以及HIV相关疾病和相关紊乱的组合疗法，包括向受试者施用抗人类免疫缺陷病毒制剂与环氧化酶-2选择性抑制剂或其异构体或其药学上可接受的盐、酯或原药组合。
• Synthesis of new 2′-deoxy-3′-substituted-α-L-threo-pentofuranonucleosides of thymine as potential antiviral agents.
  作者：Corinne Génu-Dellac、Gilles Gosselin、Jean-Louis Imbach

  DOI：10.1016/s0040-4039(00)71223-8

  日期：1991.1

  The title compounds, which are related to AZT and its congeners have been synthesized by a multi-step approach and their antiviral properties examined.
• Synthesis of L-3'-azido-3'-deoxythymidine (L-AZT) and its stereoisomers
  作者：Jesper Wengel、Jesper Lau、Erik B. Pedersen、Carsten M. Nielsen

  DOI：10.1021/jo00011a026

  日期：1991.5

  We report the first synthesis of the L isomer of 3'-azido-3'-deoxythymidine (L-AZT). L-Arabinose was used as starting material for preparation of appropriately protected alpha,beta-unsaturated aldehyde 5. Michael-type addition of azide to 5 gave 3-azido-2,3-dideoxypentofuranoses 7 and 8 suitable for nucleoside coupling with silylated thymine to afford after deprotection L-AZT (11), 1-(3-azido,-2,3-dideoxy-alpha-L-erythro-pentofuranosyl)thymine (12), 1-(3-azido-2,3-dideoxy-beta-L-threo-pentofuranosyl)thymine (13) and 1-(3-azido-2,3-dideoxy-alpha-L-threo-pento-furanosyl)thymine (14). Anti-HIV activity of L-AZT is discussed.
• OSUMI, KENJI;SUGIMURA, HIDEYUKI, NOGUTI KEHNKYUDZE DZIXO,(1990) N3, S. 17-22
  作者：OSUMI, KENJI、SUGIMURA, HIDEYUKI

  DOI：——

  日期：——
• WILSON, JEFFREY D.
  作者：WILSON, JEFFREY D.

  DOI：——

  日期：——