2-[[2-(二乙基氨基)乙基]硫代]-1,3,2-二氧杂磷杂环己烷 2-氧化物 | 58607-59-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-[[2-(二乙基氨基)乙基]硫代]-1,3,2-二氧杂磷杂环己烷 2-氧化物
• 中文别名: 2-[[2-(二乙基氨基)乙基]硫代]-1,3,2-二氧杂磷杂环己烷2-氧化物
• 英文名称: Diethyl-[2-(2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-ylsulfanyl)-ethyl]-amine
• 英文别名: Phosphorothioic acid, S-(2-diethylaminoethyl) O,O-cyclic trimethylene ester；N,N-diethyl-2-[(2-oxo-1,3,2λ5-dioxaphosphinan-2-yl)sulfanyl]ethanamine
• CAS: 58607-59-3
• 化学式: C₉H₂₀NO₃PS
• 分子量: 253.302
• InChiKey: LOPDJGDOYORFPQ-UHFFFAOYSA-N

物化性质

• 沸点：
  313.0±44.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  64.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N,N-二乙基氯乙胺 、 以 苯 为溶剂， 生成 2-[[2-(二乙基氨基)乙基]硫代]-1,3,2-二氧杂磷杂环己烷 2-氧化物
  参考文献：
  名称：

  Synthesis and Properties of 2-S-[2'-(N,N-Dialkylamino)ethyl]thio-1,3,2-dioxaphosphorinane 2-Oxide and of the Corresponding Quaternary Derivatives as Potential Nontoxic Antiglaucoma Agents

  摘要：

  A new series of cyclic organophosphorus esters, 2-S-[2'-N,N-dialkylamino)ethyl]thio-1,3,2-dioxaphosphorinane 2-oxide and their quaternary derivatives, was synthesized and studied as potential antiglaucoma agents. Thes compounds inhibit acetylcholinesterase (E.C.3.1.1.7)at a bimoecular rate constant (ki) in the range of 10(3)-10(4) M-1 min-1. Values of the affinity (K) and phosphorylation (k') rate constants for this enzyme indicate that k' is responsible for the relatively low values of ki as compared with similar data for the open-chain analogues, O,O-diethyl phosphorothiolates (10(6) M-1 min-1). The mammalian toxicity of the new compounds in terms of acute LD50 values in mice is 1-3 x 10(3) less than that of phospholine, an open-chain analogue. In an initial clinical trial, one member of the new series (alkyl = C2H5) caused a significant decrease of intraocular pressure in aphakic glaucoma, while phospholine proved to be ineffective.

  DOI：

  10.1021/jm00228a600

文献信息

• Synthesis and Properties of 2-S-[2'-(N,N-Dialkylamino)ethyl]thio-1,3,2-dioxaphosphorinane 2-Oxide and of the Corresponding Quaternary Derivatives as Potential Nontoxic Antiglaucoma Agents
  作者：Gavriel Amitai、Yacov Ashani、Yona Grunfeld、Asher Kalir、Sasson Cohen

  DOI：10.1021/jm00228a600

  日期：1976.6

  A new series of cyclic organophosphorus esters, 2-S-[2'-N,N-dialkylamino)ethyl]thio-1,3,2-dioxaphosphorinane 2-oxide and their quaternary derivatives, was synthesized and studied as potential antiglaucoma agents. Thes compounds inhibit acetylcholinesterase (E.C.3.1.1.7)at a bimoecular rate constant (ki) in the range of 10(3)-10(4) M-1 min-1. Values of the affinity (K) and phosphorylation (k') rate constants for this enzyme indicate that k' is responsible for the relatively low values of ki as compared with similar data for the open-chain analogues, O,O-diethyl phosphorothiolates (10(6) M-1 min-1). The mammalian toxicity of the new compounds in terms of acute LD50 values in mice is 1-3 x 10(3) less than that of phospholine, an open-chain analogue. In an initial clinical trial, one member of the new series (alkyl = C2H5) caused a significant decrease of intraocular pressure in aphakic glaucoma, while phospholine proved to be ineffective.