ethyl 2-cyano-2-(5'-methoxyindan-1'-ylidene)acetate | 80370-84-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: ethyl 2-cyano-2-(5'-methoxyindan-1'-ylidene)acetate
• 英文别名: Ethyl 2-cyano-2-(5-methoxy-2,3-dihydroinden-1-ylidene)acetate
• CAS: 80370-84-9
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: QSLSNWSHYYUPBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-cyano-2-(5'-methoxyindan-1'-ylidene)acetate 在 lithium aluminium tetrahydride 、 硫酸 、 氢溴酸 作用下， 以 四氢呋喃 、 乙醇 、 水 、 溶剂黄146 为溶剂， 生成 spiro[2,3-dihydroindene-1,3'-pyrrolidine]-5-ol;hydrobromide
  参考文献：
  名称：

  被设计为Profdol刚性类似物的某些螺[茚满-1,3'-吡咯烷]衍生物的合成和镇痛活性

  摘要：

  合成了螺环[茚满-1,3'-吡咯烷]的芳香族羟基化衍生物，设计为异丙酚的构象受限类似物，并在小鼠中进行了镇痛和其他中枢神经系统活动的药理学评估。在扭体试验和热板试验中，合成的化合物均不如普萘洛尔有效，但4-羟基衍生物在试验中表现出可待因水平的镇痛作用。

  DOI：

  10.1002/jps.2600710306
• 作为产物：
  描述：

  5-甲氧基-1-茚酮 、 氰乙酸乙酯 在 乙酸铵 、 溶剂黄146 作用下， 以 苯 为溶剂， 以50.8%的产率得到ethyl 2-cyano-2-(5'-methoxyindan-1'-ylidene)acetate
  参考文献：
  名称：

  被设计为Profdol刚性类似物的某些螺[茚满-1,3'-吡咯烷]衍生物的合成和镇痛活性

  摘要：

  合成了螺环[茚满-1,3'-吡咯烷]的芳香族羟基化衍生物，设计为异丙酚的构象受限类似物，并在小鼠中进行了镇痛和其他中枢神经系统活动的药理学评估。在扭体试验和热板试验中，合成的化合物均不如普萘洛尔有效，但4-羟基衍生物在试验中表现出可待因水平的镇痛作用。

  DOI：

  10.1002/jps.2600710306

文献信息

• Conformationally Constrained Phosphotyrosyl Mimetics Designed as Monomeric src Homology 2 Domain Inhibitors
  作者：Terrence R. Burke、Joseph J. Barchi、Clifford George、Gert Wolf、Steven E. Shoelson、Xinjian Yan

  DOI：10.1021/jm00008a017

  日期：1995.4

  Inhibitors of specific src homology 2 (SH2) domain binding interactions could potentially afford new therapeutic approaches toward a variety of diseases, including several cancers. To date SH2 domain inhibitors have been confined to small phosphotyrosyl (pTyr)-containing peptides that appear to bind along the surface of SH2 domains with specific recognition features protruding into the protein. Among these protrusions is the pTyr residue itself, which is inserted into a well-formed binding pocket. In the present study monomeric pTyr mimetics were prepared having key aspects of their structure constrained to conformations of the bound pTyr residue observed in the previously reported X-ray structure of a pTyr-peptide bound to the Lck SH2 domain. The resulting constrained pTyr mimetics were examined for inhibitory potency ih six SH2 domain constructs: Lck, Src, Grb2, and the C-terminal SH2 domains of PLC gamma (PLC gamma-C) and the p85 subunit of PI-3 kinase (p85-C), as well as the N-terminal SH2 domain of SH PTP2. Although inhibition constants were in the millimolar range, it was observed that capping pTyr as its N-alpha-acetyl carboxamide [(L)-1] provided a roughly 2-3-fold increase in potency relative to free pTyr. Diastereomeric indanylglycine-based analogues (+/-)-3a,b were essentially inactive. Of note was methanobenzazocine (+/-)-2. While being racemic and a partial pTyr structure, this analogue retained full binding potency of the enantiomerically pure N-alpha-acetyl pTyr amide (L)-1. Modification and elaboration of 2 could potentially result in small molecule inhibitors having greater potency.
• The Synthesis and Analgesic Activities of Some Spiro[indan-l,3'-pyrrolidine] Derivatives Designed as Rigid Analogs of Profadol
  作者：P.A. crooks、R. Sommerville

  DOI：10.1002/jps.2600710306

  日期：1982.3

  Aromatic hydroxylated derivatives of spiro[indan-1,3'-pyrrolidine], designed as conformationally restricted analogs of profadol, were synthesized and pharmacologically evaluated in mice for analgesia and other central nervous system activities. None of the compounds synthesized were as potent as profadol in writhing and hot plate tests, but the 4-hydroxy derivative exhibited codeine-level analgesia

  合成了螺环[茚满-1,3'-吡咯烷]的芳香族羟基化衍生物，设计为异丙酚的构象受限类似物，并在小鼠中进行了镇痛和其他中枢神经系统活动的药理学评估。在扭体试验和热板试验中，合成的化合物均不如普萘洛尔有效，但4-羟基衍生物在试验中表现出可待因水平的镇痛作用。