N-(2-methoxyethyl)-N'-methylthiourea | 81467-03-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫脲类
• 英文名称: N-(2-methoxyethyl)-N'-methylthiourea
• 英文别名: 1-(2-methoxyethyl)-3-methylthiourea；3-(2-Methoxyethyl)-1-methylthiourea
• CAS: 81467-03-0
• 化学式: C₅H₁₂N₂OS
• mdl: MFCD06088328
• 分子量: 148.229
• InChiKey: SXKORBPTPJTBJG-UHFFFAOYSA-N

物化性质

• 熔点：
  47-48 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  196.2±42.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  65.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-methoxyethyl)-N'-methylthiourea 在 哌啶 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 (2Z,5Z)-5-{[1-(2,4-Difluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]me thylene}-2-[(2-methoxyethyl)imino]-3-methyl-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Discovery, synthesis and SAR analysis of novel selective small molecule S1P4-R agonists based on a (2Z,5Z)-5-((pyrrol-3-yl)methylene)-3-alkyl-2-(alkylimino)thiazolidin-4-one chemotype

  摘要：

  High affinity and selective S1P(4) receptor (S1P(4)-R) small molecule agonists may be important proof-of-principle tools used to clarify the receptor biological function and effects to assess the therapeutic potential of the S1P4-R in diverse disease areas including treatment of viral infections and thrombocytopenia. A high-throughput screening campaign of the Molecular Libraries-Small Molecule Repository was carried out by our laboratories and identified (2Z,5Z)-5-((1-(2-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)methylene)-3-methyl-2-(methylimino) thiazolidin-4-one as a promising S1P(4)-R agonist hit distinct from literature S1P(4)-R modulators. Rational chemical modifications of the hit allowed the identification of a promising lead molecule with low nanomolar S1P(4)-R agonist activity and exquisite selectivity over the other S1P(1-3,5)-Rs family members. The lead molecule herein disclosed constitutes a valuable pharmacological tool to explore the effects of the S1P(4)-R signaling cascade and elucidate the molecular basis of the receptor function. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.049
• 作为产物：
  描述：

  异硫氰酸甲酯 、 2-甲氧基乙胺 以 乙醚 为溶剂， 以81%的产率得到N-(2-methoxyethyl)-N'-methylthiourea
  参考文献：
  名称：

  潜在的抗胰体药物。1，N2-二取代的2-氨基-5-羟基-4-甲基萘[1,2-d]噻唑鎓盐和相关化合物。

  摘要：

  描述了一系列具有体外锥虫杀灭活性的1-烷基-2-（取代的氨基）-5-羟基-4-甲基萘[1,2-d]噻唑。几种引起布鲁氏锥虫生物在10（-5）M在30分钟内完全溶解。2-氨基上疏水取代基的存在与高抗锥虫活性有关。一些已知的化合物在1位未取代的类似物也具有活性。没有一种衍生物能显着延长布鲁氏杆菌感染小鼠的存活。观察到牛血清白蛋白在体外具有抑制活性。由于这些药物与已知的锥虫病相比结构新颖，因此它们的作用机理值得进一步研究。

  DOI：

  10.1021/jm00348a009

文献信息

• Evaluation of thioamides, thiolactams and thioureas as hydrogen sulfide (H2S) donors for lowering blood pressure
  作者：Ewelina Zaorska、Tomasz Hutsch、Marta Gawryś-Kopczyńska、Ryszard Ostaszewski、Marcin Ufnal、Dominik Koszelewski

  DOI：10.1016/j.bioorg.2019.102941

  日期：2019.7

  Hydrogen sulfide (H2S) is a biologically important gaseous molecule that exhibits promising protective effects against a variety of pathological processes. For example, it was recognized as a blood pressure lowering agent. Aligned with the need for easily modifiable platforms for the H2S supply, we report here the preparation and the H2S release kinetics from a series of structurally diversified thioamides

  硫化氢（H2S）是生物学上重要的气态分子，对各种病理过程均显示出有希望的保护作用。例如，它被认为是降血压剂。为了满足对H2S供应的易于修改的平台的需求，我们在此报告了一系列结构多样化的硫代酰胺，硫代内酰胺和硫脲的制备和H2S释放动力学。基于五硫化二磷和Lawesson试剂的使用，使用了三种不同的硫磺化方法来制备目标硫代酰胺和硫代内酰胺。此外，在体内和体外研究中都评估了获得的H2S供体。测定了释放出的H2S的动力学参数，并使用两种不同的检测技术将其与NaHS和GYY4137进行了比较：荧光标记7-叠氮基-4-甲基-2H-铬-2--2-和5,5'-二硫代双（2-硝基苯甲酸），巯基探针，也称为Ellman试剂。我们已经证明，通过结构修饰可以控制从这些化合物释放H2S的量。最后，本研究显示了在麻醉大鼠中静脉注射发达供体的降压反应。
• ULRICH, P.;CERAMI, A., J. MED. CHEM., 1982, 25, N 6, 654-657
  作者：ULRICH, P.、CERAMI, A.

  DOI：——

  日期：——
• Discovery, synthesis and SAR analysis of novel selective small molecule S1P4-R agonists based on a (2Z,5Z)-5-((pyrrol-3-yl)methylene)-3-alkyl-2-(alkylimino)thiazolidin-4-one chemotype
  作者：Mariangela Urbano、Miguel Guerrero、Subash Velaparthi、Melissa Crisp、Peter Chase、Peter Hodder、Marie-Therese Schaeffer、Steven Brown、Hugh Rosen、Edward Roberts

  DOI：10.1016/j.bmcl.2011.09.049

  日期：2011.11

  High affinity and selective S1P(4) receptor (S1P(4)-R) small molecule agonists may be important proof-of-principle tools used to clarify the receptor biological function and effects to assess the therapeutic potential of the S1P4-R in diverse disease areas including treatment of viral infections and thrombocytopenia. A high-throughput screening campaign of the Molecular Libraries-Small Molecule Repository was carried out by our laboratories and identified (2Z,5Z)-5-((1-(2-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)methylene)-3-methyl-2-(methylimino) thiazolidin-4-one as a promising S1P(4)-R agonist hit distinct from literature S1P(4)-R modulators. Rational chemical modifications of the hit allowed the identification of a promising lead molecule with low nanomolar S1P(4)-R agonist activity and exquisite selectivity over the other S1P(1-3,5)-Rs family members. The lead molecule herein disclosed constitutes a valuable pharmacological tool to explore the effects of the S1P(4)-R signaling cascade and elucidate the molecular basis of the receptor function. (C) 2011 Elsevier Ltd. All rights reserved.
• Potential antitrypanosomal agents. 1,N2-Disubstituted 2-amino-5-hydroxy-4-methylnaphtho[1,2-d]thiazolium salts and related compounds
  作者：Peter Ulrich、Anthony Cerami

  DOI：10.1021/jm00348a009

  日期：1982.6

  2-amino group was associated with high antitrypanosomal activity. Some analogues unsubstituted at the 1-position, a known class of compounds, were also active. None of the derivatives significantly prolonged the survival of T. brucei infected mice. Inhibition of activity in vitro by bovine serum albumin was observed. Because of the structural novelty of these agents in comparison with known trypanocides

  描述了一系列具有体外锥虫杀灭活性的1-烷基-2-（取代的氨基）-5-羟基-4-甲基萘[1,2-d]噻唑。几种引起布鲁氏锥虫生物在10（-5）M在30分钟内完全溶解。2-氨基上疏水取代基的存在与高抗锥虫活性有关。一些已知的化合物在1位未取代的类似物也具有活性。没有一种衍生物能显着延长布鲁氏杆菌感染小鼠的存活。观察到牛血清白蛋白在体外具有抑制活性。由于这些药物与已知的锥虫病相比结构新颖，因此它们的作用机理值得进一步研究。