2-chloro-2-thioxo-1,3,2-dioxaphosphorinane | 17377-19-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫代磷酸及其衍生物
• 英文名称: 2-chloro-2-thioxo-1,3,2-dioxaphosphorinane
• 英文别名: 2-chloro-[1,3,2]dioxaphosphinane 2-sulfide；2-Chloro-2-thiono-1,3,2-dioxaphosphorinan；O,O-Trimethylenphosphorchloridthioat；2-Chloro-1,3,2lambda~5~-dioxaphosphinane-2-thione；2-chloro-2-sulfanylidene-1,3,2λ5-dioxaphosphinane
• CAS: 17377-19-4
• 化学式: C₃H₆ClO₂PS
• 分子量: 172.572
• InChiKey: LAUKEERIEDZFQE-UHFFFAOYSA-N

物化性质

• 沸点：
  204.7±7.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-2-thioxo-1,3,2-dioxaphosphorinane 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 C₃H₇O₃PS
  参考文献：
  名称：

  AKR1C3抑制剂及医药用途

  摘要：

  本发明提供下式化合物及其药学上可接受的盐或溶剂合物或同位素取代化合物的AKR1C3抑制剂及医药用途

  公开号：

  CN112004799B
• 作为产物：
  描述：

  1,3-丙二醇 在 三氯硫磷 、 N,N-二异丙基乙胺 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以3.5 g的产率得到2-chloro-2-thioxo-1,3,2-dioxaphosphorinane
  参考文献：
  名称：

  AKR1C3抑制剂及医药用途

  摘要：

  本发明提供下式化合物及其药学上可接受的盐或溶剂合物或同位素取代化合物的AKR1C3抑制剂及医药用途

  公开号：

  CN112004799B

文献信息

• Novel steroid sulfatase inhibitors based on <i>N</i> ‐thiophosphorylated 3‐(4‐aminophenyl)‐coumarin‐7‐O‐sulfamates
  作者：Mateusz Daśko、Sebastian Demkowicz、Karol Biernacki、Amira Harrous、Janusz Rachon、Witold Kozak、Aleksandra Martyna、Maciej Masłyk、Konrad Kubiński、Anna Boguszewska‐Czubara

  DOI：10.1002/ddr.21569

  日期：2019.9

  In the present work, we described convenient methods for the synthesis of N‐thiophosphorylated 3‐(4‐aminophenyl)‐coumarin‐7‐O‐sulfamates as steroid sulfatase (STS) inhibitors. To design the structures of the potential STS inhibitors, molecular modeling techniques were used. A computational docking method was used to determine the binding modes of the synthesized inhibitors as well as to identify potential

  在当前的工作中，我们描述了合成甾族硫酸酯酶（STS）抑制剂的N-硫代磷酸化的3-（4-氨基苯基）-香豆素-7- O-氨基磺酸盐的简便方法。为了设计潜在的STS抑制剂的结构，使用了分子建模技术。使用计算机对接方法确定合成抑制剂的结合模式，并确定抑制剂上特定功能基团与酶活性位点中存在的氨基酸残基之间的潜在相互作用。合成的化合物的抑制活性用从人胎盘分离的STS在酶促测定中进行了测试。在一组新合成的化合物中，9e表现在与IC的酶测定的最高抑制活性50 0.201μM的值（IC 50的值667-COUMATE在相同的测试是0.062μM）。此外，我们试图验证所获得的STS抑制剂在细胞系实验中是否能够有效通过细胞膜。在我们的研究过程中，我们在抑制剂存在下（浓度为100 nM）孵育后，确定了MCF-7细胞系中的STS活性。在此评估中，我们包括了新合成的化合物9a-g及其N-磷酸化的类似物6a-h，其合成
• 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.
• Predvoditelev,D.A. et al., Journal of general chemistry of the USSR, 1974, vol. 44, p. 720 - 723
  作者：Predvoditelev,D.A. et al.

  DOI：——

  日期：——
• Thiophosphorylated derivatives of meta- and ortho-hydroxybenzaldehydes in one-step syntheses of novel calix[4]resorcinols
  作者：Irina R. Knyazeva、Victoria I. Matveeva、Victor V. Syakaev、Bulat M. Gabidullin、Aidar T. Gubaidullin、Margit Gruner、Wolf D. Habicher、Alexander R. Burilov、Michael A. Pudovik

  DOI：10.1016/j.tetlet.2014.11.019

  日期：2014.12

  Thiophosphorylated derivatives of meta- and ortho-hydroxybenzaldehydes take part in one-step, acid-catalyzed condensations with resorcinol and its derivatives. As a result, new calix[4]resorcinols, which contain four 2-thioxo-1,3,2-dioxaphosphorinane fragments on the aromatic substituents of the calixarene matrix, have been synthesized. In this case, macrocyclic products are formed as rccc- (cone or boat conformation) and/or rctt- (chair conformation) diastereomers, the ratio of which depends on the structure of the starting reagents. The obtained products have been isolated and their structures determined by NMR methods and single-crystal X-ray diffraction. The spectral differences of conformational isomers of the prepared macrocycles have been demonstrated. (C) 2014 Elsevier Ltd. All rights reserved.
• Predvoditelev,D.A. et al., Journal of general chemistry of the USSR, 1976, vol. 46, p. 39 - 42
  作者：Predvoditelev,D.A. et al.

  DOI：——

  日期：——