1-(2-deoxy-4-thio-α-D-ribofuranosyl)uracil | 134111-34-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 1-(2-deoxy-4-thio-α-D-ribofuranosyl)uracil
• 英文别名: 1-(2-deoxy-4-thio-alpha-D-ribofuranosyl)uracil；1-[(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)thiolan-2-yl]pyrimidine-2,4-dione
• CAS: 134111-34-5
• 化学式: C₉H₁₂N₂O₄S
• 分子量: 244.271
• InChiKey: DDRFKXKKBYNNSO-BBVRLYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-deoxy-4-thio-α-D-ribofuranosyl)uracil 在 盐酸 作用下， 生成 尿嘧啶 、 1-((2S,4S,5R)-4,5-Dihydroxy-tetrahydro-thiopyran-2-yl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Otter, Graham P.; Elzagheid, Mohamed I.; Jones, Garry D., Journal of the Chemical Society. Perkin Transactions 2 (2001), 1998, # 11, p. 2343 - 2349

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(5-O-acetyl-2-deoxy-4-thio-β-D-erythro-pentofuranosyl)uracil 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 1-(2-deoxy-4-thio-α-D-ribofuranosyl)uracil
  参考文献：
  名称：

  Stereocontrolled preparation of cyclic xanthate; a novel synthetic route to 4-thiofuranose and 4′-thionucleoside

  摘要：

  通过环氧醇与 NaH 和 CS2 的反应制备了具有光学活性的环黄原酸盐，并发现它是合成 4-硫代-2-脱氧核糖和 4â²-硫代-2â²-脱氧核苷的有用中间体。

  DOI：

  10.1039/c39910001421

文献信息

• The Synthesis and Biological Activity of Certain 4'-Thionucleosides
  作者：John Secrist、William Parker、Kamal Tiwari、Lea Messini、Sue Shaddix、Lucy Rose、L. Lee Bennett、John Montgomery

  DOI：10.1080/15257779508012449

  日期：1995.5.1

  Abstract Results are presented on the synthesis and biological activity of several types of 4′-thionucleosides as potential anticancer agents. Detailed studies on the mechanism of action of 4′-thiothymidine are also presented.

  摘要介绍了几种类型的4'-硫代核苷作为潜在抗癌剂的合成和生物学活性。还介绍了有关4'-硫代胸苷的作用机理的详细研究。
• 2'-deoxy-4'-thioribonucleosides and their antiviral activity
  申请人：Southern Research Institute

  公开号：US05591722A1

  公开（公告）日：1997-01-07

  2'-Deoxy-4'-thio-ribonucleosides, intermediates in their production, and their use as antiviral and anticancer agents are disclosed.

  本发明揭示了2'-脱氧-4'-硫基核苷，其生产中间体以及它们作为抗病毒和抗癌剂的用途。
• Synthesis and biological activity of 2'-deoxy-4'-thio pyrimidine nucleosides
  作者：John A. Secrist、Kamal N. Tiwari、James M. Riordan、John A. Montgomery

  DOI：10.1021/jm00112a007

  日期：1991.8

  2'-Deoxy-4'-thiocytidine (7-beta), 2'-deoxy-4'-thiouridine (9), and 4'-thiothymidine (10) have been synthesized and evaluated for cytotoxicity in vitro. All these compounds were cytotoxic to L1210, H-Ep-2, and CCRF-CEM cell lines. 4'-Thiothymidine was also active against herpes simplex 1 and human cytomegalovirus in cell culture.
• US5591722A
  申请人：——

  公开号：US5591722A

  公开（公告）日：1997-01-07
• Otter, Graham P.; Elzagheid, Mohamed I.; Jones, Garry D., Journal of the Chemical Society. Perkin Transactions 2 (2001), 1998, # 11, p. 2343 - 2349
  作者：Otter, Graham P.、Elzagheid, Mohamed I.、Jones, Garry D.、MacCulloch, Alasdair C.、Walker, Richard T.、Oivanen, Mikko、Klika, Karel D.

  DOI：——

  日期：——