2-<<(diethylphosphono)methyl>thio>ethanol | 125331-03-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 2-<<(diethylphosphono)methyl>thio>ethanol
• 英文别名: diethyl <(2-hydroxyethyl)thiomethyl>phosphonate；diethyl 4-hydroxy-2-thiabutylphosphonate；diethyl 2-hydroxyethylthiomethylphosphonate；2-{[(diethylphosphono)methyl]thio}ethanol；2-(diethoxyphosphorylmethylsulfanyl)ethanol
• CAS: 125331-03-5
• 化学式: C₇H₁₇O₄PS
• 分子量: 228.249
• InChiKey: PHCBUNJOFKZTMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-<<(diethylphosphono)methyl>thio>ethanol 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 diethyl 4-adenin-9-yl-2-thiabutylphosphonate
  参考文献：
  名称：

  一种新型 PMEA 硫类似物的合成

  摘要：

  摘要 描述了一种新的 PMEA（9-（2-膦酰基-甲氧基乙基）-腺嘌呤）硫类似物的合成。该 PMEA 类似物用偏高碘酸钠氧化。制备的化合物在体外针对 HIV 逆转录酶进行了测试，并且似乎是无活性的。

  DOI：

  10.1080/00397919308018581
• 作为产物：
  描述：

  methyl (diethoxy)phosphonyldithioformate 以58%的产率得到
  参考文献：
  名称：

  Makomo Hubert, Masson Serge, Saquet Monique, Tetrahedron, 50 (1994) N 34, S 10277-10288

  摘要：

  DOI：

文献信息

• Antiviral purine derivatives
  申请人：Beecham Group p.l.c.

  公开号：US05108994A1

  公开（公告）日：1992-04-28

  Compounds of formula (I), and pharmaceutically acceptable salts thereof: ##STR1## wherein R.sub.1 is hydroxy or amino; R.sub.2 is hydrogen or amino; R.sub.3 is hydrogen, hydroxymethyl or acyloxymethyl; R.sub.4 is a group of formula: ##STR2## wherein R.sub.5 and R.sub.6 are independently selected from hydrogen, C.sub.1-6 alkyl and optionally substituted phenyl; or R.sub.3 and R.sub.4 together are: ##STR3## wherein R.sub.6 is as defined above; having antiviral activity, processes for their preparation and their pharmaceutical use.

  式(I)的化合物及其药学上可接受的盐：##STR1##其中R.sub.1是羟基或氨基；R.sub.2是氢或氨基；R.sub.3是氢、羟甲基或醋氧甲基；R.sub.4是下式的基团：##STR2##其中R.sub.5和R.sub.6分别选自氢、C.sub.1-6烷基和可选择取代的苯基；或R.sub.3和R.sub.4一起是：##STR3##其中R.sub.6如上所定义；具有抗病毒活性，其制备方法及其药用。
• Acyclic purine phosphonate analogs as antiviral agents. Synthesis and structure-activity relationships
  作者：Choung Un Kim、Bing Yu Luh、Peter F. Misco、Joanne J. Bronson、Michael J. M. Hitchcock、Ismail Ghazzouli、John C. Martin

  DOI：10.1021/jm00166a019

  日期：1990.4

  observed by the bovine brain guanylate kinase. Since all isosteric analogues of PMEG (7-9) were not inhibitory against HSV-1 and HSV-2, the presence of the 3'-oxygen atom in the PME purines proved critical for anti-HSV activity. Introduction of the 1'-methyl group on the PMEG side chain significantly reduced its anti-HSV activity. Analogue 11, which is a mimic of the phosphate by incorporation of the alpha

  合成了一系列9-（膦酰基烷基）嘌呤，它们是9- [2-（膦酰基甲氧基）乙基]嘌呤的类似物（鸟嘌呤，PMEG，1；腺嘌呤，PMEA，2）。测试了类似物对1型和2型单纯疱疹病毒（HSV-1和HSV-2），人巨细胞病毒（HCMV），罗氏鼠白血病病毒（R-MuLV）和1型人类免疫缺陷病毒（HIV-1）的活性）。随着烷基链长度的变化，嘌呤碱和膦酰基甲氧基官能团之间有两个碳原子，从而实现了最佳活性。尽管与PMEG的结构相似且pKa2值接近8，但牛脑鸟苷酸激酶未观察到8的磷酸化。由于所有PMEG的等距类似物（7-9）均不能抑制HSV-1和HSV-2，因此存在3' PME嘌呤中的-氧原子被证明对抗HSV活性至关重要。在PMEG侧链上引入1'-甲基会大大降低其抗HSV活性。通过掺入α，α-二氟碳来模拟磷酸盐的类似物11对HSV-1和HSV-2无效。这些结果表明，PME嘌呤的抗HSV活性的结构要求似乎非常严格。
• Phosphonomethylthio-alkoseypureine derivatives, intermediate products for their preparation and pharmaceutical compositions containing them
  申请人：BEECHAM GROUP PLC

  公开号：EP0399743A1

  公开（公告）日：1990-11-28

  Compounds of formula (I), and pharmaceutically acceptable salts thereof: wherein R₁ is hydroxy or amino; R₂ is hydrogen or amino; R₃ is hydrogen, hydroxymethyl or acyloxymethyl; R₄ is a group of formula: wherein R₅ and R₆ are independently selected from hydrogen, C₁₋₆ alkyl and optionally substituted phenyl; or R₃ and R₄ together are: wherein R₆ is as defined above; having antiviral activity, processes for their preparation and their pharmaceutical use.

  式 (I) 的化合物及其药学上可接受的盐类： 其中 R₁ 是羟基或氨基； R₂ 是氢或氨基 R₃ 是氢、羟甲基或酰氧基甲基； R₄ 是式中的基团： 其中 R₅ 和 R₆ 独立选自氢、C₁₋₆ 烷基和任选取代的苯基；或 R₃ 和 R₄ 合在一起为 其中 R₆ 如上文所定义； 具有抗病毒活性，其制备工艺和药物用途。
• Reductions of phosphonodithioformates: Syntheses of β-phosphonyl thiols and hemidithioacetals.
  作者：Hubert Makomo、Serge Masson、Monique Saquet

  DOI：10.1016/s0040-4020(01)81760-9

  日期：1994.8

  The phosphonodithioformates appeared versatile precursors to the (mercaptomethyl)phosphonates and derivatives, through sodium borohydride reduction in acetonitrile heated under reflux. By contrast, when the reduction was performed at room temperature with sodium borohydride, the (mercapto-alkylthio-methyl)phosphonates were exclusively obtained; reduction with BH3-Me(2)S (BMS) or within lithium diisopropylaminoborohydride also led to these hemidithioacetals. The aforementioned products of reduction were characterized by the syntheses of various derivatives. In particular, S-phosphonyl trithiocarbonates, N-phenyl imidodithiocarbonate and dithiocarbamate were prepared.
• US5108994A
  申请人：——

  公开号：US5108994A

  公开（公告）日：1992-04-28