5'-chloro-2',3'-didehydro-3',5'-dideoxythymidine | 33799-54-1

• 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: 5'-chloro-2',3'-didehydro-3',5'-dideoxythymidine
• 英文别名: 1-[(2R,5S)-5-(chloromethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 33799-54-1
• 化学式: C₁₀H₁₁ClN₂O₃
• 分子量: 242.662
• InChiKey: XVMHDVJEQNEXPN-JGVFFNPUSA-N

物化性质

• 密度：
  1.371±0.06 g/cm3(Predicted)

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：
  0.4
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5'-chloro-2',3'-didehydro-3',5'-dideoxythymidine 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 2-methyl-5-(thymin-1-yl)furan
  参考文献：
  名称：

  Independent Synthesis and Fate Studies of Impurities in Process Intermediates of the Anti-AIDS Drug d4T

  摘要：

  Impurities in isolated intermediates in a process to prepare d4T were identified, independently synthesized, and then taken through the process to determine their ultimate fate. Some of the products from these fate studies were also independently synthesized and used in the validation of impurity assay methods.

  DOI：

  10.1021/op970126p
• 作为产物：
  描述：

  司他夫定 在 氯化亚砜 作用下， 以 六甲基磷酰三胺 为溶剂， 以70%的产率得到5'-chloro-2',3'-didehydro-3',5'-dideoxythymidine
  参考文献：
  名称：

  一些5'-硫代呋喃呋喃糖基嘧啶的合成作为潜在的抗肿瘤药物。

  摘要：

  描述了迄今未知的2'，3'-didehydro-3'-deoxythymidine衍生的5'-硫醚，亚砜，砜的制备方法[ 4-9 ]。该合成的关键步骤是通过硫代烷基钠盐进行卤素的亲核取代，以及随后将硫基氧化为砜和亚砜类似物。已评估这些化合物对L1210细胞增殖的抑制作用。除了显示中等活性（IC 50为90.2μM）的5'-乙硫基类似物4b外，所有化合物均无活性。©1997爱思唯尔科学有限公司。

  DOI：

  10.1016/s0040-4039(97)10025-9

文献信息

• Synthesis of 5′-Thioalkyl, Sulfoxide and Sulfone Pyrimidine Nucleosides
  作者：L. A. Agrofoglio、F. Girard、F. Fleury、S. Léonce

  DOI：10.1080/15257779908041508

  日期：1999.4

  The preparation of 5'-thioalkyl, sulfoxide and sulfone pyrimidine nucleosides is [4-11] is described. The key steps of this synthesis are the nucleophilic displacements of a chlorine by a thioalkyl sodium salt or the direct introduction of the thioalkyl group under Mitsunobu conditions.
• Independent Synthesis and Fate Studies of Impurities in Process Intermediates of the Anti-AIDS Drug d4T
  作者：Jayachandra P. Reddy、J. Gregory Reid、Deborah A. Renner、Sandra L. Quinlan、Douglas G. Weaver、Bang-Chi Chen、Derron R. Stark、Qi Gao

  DOI：10.1021/op970126p

  日期：1998.5.1

  Impurities in isolated intermediates in a process to prepare d4T were identified, independently synthesized, and then taken through the process to determine their ultimate fate. Some of the products from these fate studies were also independently synthesized and used in the validation of impurity assay methods.
• Synthesis of Some 5′-Thiopentofuranosylpyrimidines as Potential Anti-tumor Agents.
  作者：Frédéric Girard、Stephane Leonce、Luigi A Agrofoglio

  DOI：10.1016/s0040-4039(97)10025-9

  日期：1997.10

  The preparation of hitherto unknown, 2′,3′-didehydro-3′-deoxythymidine derived 5′-thioether, sulfoxide, sulfone [4–9] is described. The key steps of this synthesis are the nucleophilic displacements of a halogen by a thioalkyl sodium salt, and the later oxidation of the sulfur group into sulfone and sulfoxide analogues. These compounds have been evaluated for their inhibition of L1210 cells proliferation

  描述了迄今未知的2'，3'-didehydro-3'-deoxythymidine衍生的5'-硫醚，亚砜，砜的制备方法[ 4-9 ]。该合成的关键步骤是通过硫代烷基钠盐进行卤素的亲核取代，以及随后将硫基氧化为砜和亚砜类似物。已评估这些化合物对L1210细胞增殖的抑制作用。除了显示中等活性（IC 50为90.2μM）的5'-乙硫基类似物4b外，所有化合物均无活性。©1997爱思唯尔科学有限公司。