1-(5-O-acetyl-2-deoxy-3-O-methanesulfonyl-4-ethynyl-3-D-threo-pentofuranosyl)thymine | 744217-12-7

• 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: 1-(5-O-acetyl-2-deoxy-3-O-methanesulfonyl-4-ethynyl-3-D-threo-pentofuranosyl)thymine
• 英文别名: 1-(5-O-Acetyl-2-deoxy-3-O-methanesulfonyl-4-ethynyl-β-D-threo-pentofuranosyl)thymine；1-(5-O-Acetyl-2-deoxy-3-O-methanesulfonyl-4-ethynyl-beta-D-threo-pentofuranosyl)thymine；[(2R,3R,5R)-2-ethynyl-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-3-methylsulfonyloxyoxolan-2-yl]methyl acetate
• CAS: 744217-12-7
• 化学式: C₁₅H₁₈N₂O₈S
• 分子量: 386.383
• InChiKey: NJDZJJOQJSHXIC-LALPHHSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(5-O-acetyl-2-deoxy-3-O-methanesulfonyl-4-ethynyl-3-D-threo-pentofuranosyl)thymine 在 敌草腈 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of a highly active new anti-HIV agent 2′,3′-Didehydro-3′-deoxy-4′-ethynylthymidine

  摘要：

  Compounds having methyl, vinyl, and ethynyl groups at the 4'-position of stavudine (d4T: 2',3'-didehydro-3'-deoxythymidine) were synthesized. The compounds were assayed for their ability to inhibit the replication of HIV in cell culture. The 4'-ethynyl analogue (15) was found to be more potent and less toxic than the parent compound stavudine. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.009
• 作为产物：
  描述：

  1-(2,5-dideoxy-5-iodo-β-D-threo-pentofuranosyl)thymine 在 吡啶 、 1,5-二氮杂双环[4.3.0]壬-5-烯 、 四丁基氟化铵 、 氨 、 二甲基二环氧乙烷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 95.5h， 生成 1-(5-O-acetyl-2-deoxy-3-O-methanesulfonyl-4-ethynyl-3-D-threo-pentofuranosyl)thymine
  参考文献：
  名称：

  Anti-viral nucleoside analogs and methods for treating viral infections, especially HIV infections

  摘要：

  本发明涉及根据一般式I、II、III、IV或V的新化合物： 其中B是根据以下结构的核苷酸碱基： 以及规范中定义的其余变量，以及包含这些化合物的药物组合物。这些化合物可用作抗病毒剂，用于病毒治疗。

  公开号：

  US09126971B2

文献信息

• A NEW APPROACH TO THE SYNTHESIS OF 4′-CARBON-SUBSTITUTED NUCLEOSIDES: DEVELOPMENT OF A HIGHLY ACTIVE ANTI-HIV AGENT 2′, 3′-DIDEHYDRO-3′-DEOXY-4′-ETHYNYLTHYMIDINE
  作者：Kazuhiro Haraguchi、Shingo Takeda、Masanori Sumino、Hiromichi Tanaka、Ginger E. Dutschman、Yung-Chi Cheng、Takao Nitanda、Masanori Baba

  DOI：10.1081/ncn-200059774

  日期：2005.4.1

  Oxidation of 3'-O-TBDMS-4',5'-unsaturated thymidine 3 with dimethyldioxirane (DMDO) allowed the isolation of the epoxide 4. Upon reacting with organosilicon reagents in the Presence of SnCl4, 4 underwent stereoselective ring opening to give 4'-alpha-allyl (6), 4'-alpha-(2-bromoallyl) (7), 4'-alpha(cyclopenten-3-yl) (8), and 4'-alpha-cyano (9) derivatives of thymidine. Reactions of the 3'-epimer 12 with organoaluminum reagents gave 4-alpha-methyl (13), 4'-alpha-vinyl (14), and 4'-alpha-ethynyl (15) analogues. Compounds 13-15 were transformed into corresponding 2',3'-didehydro-3'-deoxy derivatives. Evaluation of their ability to inhibit the replication of HIV in cell culture showed that 4'-ethynyl-d4T (19) is more potent and less toxic than the parent compound d4T.
• Anti-viral nucleoside analogs and methods for treating viral infections, especially hiv infections
  申请人：Yale University

  公开号：EP2298783B1

  公开（公告）日：2017-12-06
• US7589078B2
  申请人：——

  公开号：US7589078B2

  公开（公告）日：2009-09-15
• US8193165B2
  申请人：——

  公开号：US8193165B2

  公开（公告）日：2012-06-05