2-(5-methoxythiophen-3-yl)ethylamine oxalate | 157613-41-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(5-methoxythiophen-3-yl)ethylamine oxalate
• 英文别名: 2-(5-methoxythiophen-2-yl)ethan-1-amine；2-(5-Methoxythiophen-3-yl)ethanamine
• CAS: 157613-41-7
• 化学式: C₇H₁₁NOS
• 分子量: 157.236
• InChiKey: PUXJVBWGXIZXOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  63.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(5-methoxythiophen-3-yl)ethylamine oxalate 在 sodium tetrahydroborate 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 5.25h， 生成 2-(4-hydroxyphenyl)-N-[2-(5-methoxythiophen-3-yl)ethyl]-N-propylacetamide
  参考文献：
  名称：

  Synthesis and evaluation of 2-(5-methoxythiophen-3-yl)ethylamines as potential dopamine agonists

  摘要：

  The synthesis of 2-(5-methoxythiophen-3-yl)ethylamine and some derivatives bearing propyl and 2-phenylethyl substituents on the amino group has been described. The affinities for dopamine D-1 and D-2 receptors were evaluated by binding assays on rat striatum. None of the compounds show affinity for the D-1 receptor. In the D-2 binding assays the N-propyl-N-(2- phenylethyl) derivatives show affinity similar to that of the reference compound N-n-propyl-N-(2-phenylethyl)-2-(3-hydroxy- phenyl)ethylamine (1, RU 24213). In preliminary behavioral tests [2-(5-methoxythiophen-3-yl)ethyl]phenethylpropylamine behaves as a selective D-2 agonist.

  DOI：

  10.1016/0223-5234(94)90069-8
• 作为产物：
  描述：

  2-methoxy-4-(2-nitroethenyl)thiophene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以80%的产率得到2-(5-methoxythiophen-3-yl)ethylamine oxalate
  参考文献：
  名称：

  Synthesis and evaluation of 2-(5-methoxythiophen-3-yl)ethylamines as potential dopamine agonists

  摘要：

  The synthesis of 2-(5-methoxythiophen-3-yl)ethylamine and some derivatives bearing propyl and 2-phenylethyl substituents on the amino group has been described. The affinities for dopamine D-1 and D-2 receptors were evaluated by binding assays on rat striatum. None of the compounds show affinity for the D-1 receptor. In the D-2 binding assays the N-propyl-N-(2- phenylethyl) derivatives show affinity similar to that of the reference compound N-n-propyl-N-(2-phenylethyl)-2-(3-hydroxy- phenyl)ethylamine (1, RU 24213). In preliminary behavioral tests [2-(5-methoxythiophen-3-yl)ethyl]phenethylpropylamine behaves as a selective D-2 agonist.

  DOI：

  10.1016/0223-5234(94)90069-8

文献信息

• Discovery of Dihydropyrrolo[1,2-<i>a</i>]pyrazin-3(4<i>H</i>)-one-Based Second-Generation GluN2C- and GluN2D-Selective Positive Allosteric Modulators (PAMs) of the <i>N</i>-Methyl-<scp>d</scp>-Aspartate (NMDA) Receptor
  作者：Matthew P. Epplin、Ayush Mohan、Lynnea D. Harris、Zongjian Zhu、Katie L. Strong、John Bacsa、Phuong Le、David S. Menaldino、Stephen F. Traynelis、Dennis C. Liotta

  DOI：10.1021/acs.jmedchem.9b01733

  日期：2020.7.23

  to increase glutamate potency 2-fold, increase the response to maximally effective concentration of agonist 4-fold, and the racemate is brain-penetrant. These compounds are useful second-generation in vitro tools and a promising step toward in vivo tools for the study of positive modulation of GluN2C- and GluN2D-containing NMDA receptors.

  所述Ñ甲基d天冬氨酸受体（NMDAR）为离子通道介导的是缓慢，钙2+谷氨酸能突触传递中的中枢神经系统（CNS）可透过的组件。已知NMDAR在基本的神经功能中起重要作用，其功能障碍与多种CNS疾病有关。在这里，我们报告发现具有二氢吡咯并[1,2 - a ]吡嗪-3（4 H）-一个核心的第二代GluN2C / D选择性NMDAR阳性变构调节剂（PAM）。原型R -（+）-EU-1180-453，与第一代原型CIQ相比，在双受体反应，亲脂性和水溶性方面所需浓度提高了log单位，并且cLogP降低了一个log单位。此外，发现R -（+）-EU-1180-453可将谷氨酸效能提高2倍，对激动剂的最大有效浓度的响应也可提高4倍，并且外消旋物具有大脑渗透性。这些化合物是有用的第二代体外工具，对于研究含GluN2C和含GluN2D的NMDA受体的正向调节的体内工具迈出了有希望的一步。
• Synthesis and evaluation of 2-(5-methoxythiophen-3-yl)ethylamines as potential dopamine agonists
  作者：M Cardellini、GM Cingolani、F Claudi、A Di Stefano、G Giorgioni、F Cantalamessa、A Cagnotto、M Skorupska

  DOI：10.1016/0223-5234(94)90069-8

  日期：1994.1

  The synthesis of 2-(5-methoxythiophen-3-yl)ethylamine and some derivatives bearing propyl and 2-phenylethyl substituents on the amino group has been described. The affinities for dopamine D-1 and D-2 receptors were evaluated by binding assays on rat striatum. None of the compounds show affinity for the D-1 receptor. In the D-2 binding assays the N-propyl-N-(2- phenylethyl) derivatives show affinity similar to that of the reference compound N-n-propyl-N-(2-phenylethyl)-2-(3-hydroxy- phenyl)ethylamine (1, RU 24213). In preliminary behavioral tests [2-(5-methoxythiophen-3-yl)ethyl]phenethylpropylamine behaves as a selective D-2 agonist.