2-乙基-3-(4-甲氧基苯基)-2-环氧乙烷羧酸 | 769073-61-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-乙基-3-(4-甲氧基苯基)-2-环氧乙烷羧酸
• 中文别名: (2R)-2-乙酰氨基-3-(2,3,4-三羟基丁基硫烷基)丙酸
• 英文名称: 2-ethyl-3-(4-methoxyphenyl)oxirane-2-carboxylic acid
• CAS: 769073-61-2
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: JWCUMGKSHWZEAG-UHFFFAOYSA-N

物化性质

• 沸点：
  383.7±42.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  2-乙基-3-(4-甲氧基苯基)-2-环氧乙烷羧酸 在 咪唑 、 4-二甲氨基吡啶 、 正丁基锂 、 三溴化硼 、 sodium hydride 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.58h， 生成 (+/-)-N-(4-(2-(dimethylamino)ethoxy)phenyl)-3-ethyl-6-triisopropylsiloxy-2-(4-triisopropylsiloxyphenyl)-1H-indene-1-carboxamide
  参考文献：
  名称：

  Differential Response of Estrogen Receptor Subtypes to 1,3-Diarylindene and 2,3-Diarylindene Ligands

  摘要：

  Estrogen receptors (ERs) control transcription of genes important for normal human development and reproduction. The signaling networks are complex, and there is a need for a molecular level understanding of the roles of receptor subtypes ER alpha and ER beta in normal physiology and as therapeutic targets. We synthesized two series of ER ligands, based on a common indene scaffold, in an attempt to develop compounds that can selectively modulate ER-mediated transcription. The 3-ethyl-1,2-diarylindenes, utilizing an amide linker for the 1-aryl extension, bind weakly to the ERs. The 2,3-diarylindenes bind with high affinity to the ER subtypes and demonstrate a range of different biological activities, both in transcriptional reporter gene assays and inhibition of estradiol-stimulated proliferation of MCF-7 cells. Several ligands differentiate between ER alpha and ER beta subtypes at an estrogen response element (ERE), displaying various levels of partial to full agonist activity at ER alpha, while antagonizing estradiol action at ER beta.

  DOI：

  10.1021/jm050226i
• 作为产物：
  描述：

  2-乙基-3-(4-甲氧基苯基)环氧乙烷-2-羧酸乙酯 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 2-乙基-3-(4-甲氧基苯基)-2-环氧乙烷羧酸
  参考文献：
  名称：

  Differential Response of Estrogen Receptor Subtypes to 1,3-Diarylindene and 2,3-Diarylindene Ligands

  摘要：

  Estrogen receptors (ERs) control transcription of genes important for normal human development and reproduction. The signaling networks are complex, and there is a need for a molecular level understanding of the roles of receptor subtypes ER alpha and ER beta in normal physiology and as therapeutic targets. We synthesized two series of ER ligands, based on a common indene scaffold, in an attempt to develop compounds that can selectively modulate ER-mediated transcription. The 3-ethyl-1,2-diarylindenes, utilizing an amide linker for the 1-aryl extension, bind weakly to the ERs. The 2,3-diarylindenes bind with high affinity to the ER subtypes and demonstrate a range of different biological activities, both in transcriptional reporter gene assays and inhibition of estradiol-stimulated proliferation of MCF-7 cells. Several ligands differentiate between ER alpha and ER beta subtypes at an estrogen response element (ERE), displaying various levels of partial to full agonist activity at ER alpha, while antagonizing estradiol action at ER beta.

  DOI：

  10.1021/jm050226i

文献信息

• Phenylglycidate stereoisomers, conversion products thereof with e.g. 2-nitrothiophenol and preparation of diltiazem
  申请人：DSM N.V.

  公开号：EP0343714A1

  公开（公告）日：1989-11-29

  The stereoisomerically pure esters of (2R,3S)-3-(4-hydroxy or 4-alkoxyphenyl)glycidic acid, which is a starting compound for the preparation of diltiazem, are prepared by stereospecific enzymatic hydrolysis. By using such an ester, it is possible to economically prepare the (2S,3S) isomer of diltiazem to the exclusion of other stereoisomers.

  (2R,3S)-3-(4-羟基或 4-烷氧基苯基)缩水甘油酯是制备地尔硫卓的起始化合物，其立体异构体纯酯是通过立体特异性酶水解制备的。通过使用这种酯类，可以经济地制备地尔硫卓的(2S,3S)异构体，而排除其他立体异构体。
• Differential Response of Estrogen Receptor Subtypes to 1,3-Diarylindene and 2,3-Diarylindene Ligands
  作者：Nicola J. Clegg、Sreenivasan Paruthiyil、Dale C. Leitman、Thomas S. Scanlan

  DOI：10.1021/jm050226i

  日期：2005.9.1

  Estrogen receptors (ERs) control transcription of genes important for normal human development and reproduction. The signaling networks are complex, and there is a need for a molecular level understanding of the roles of receptor subtypes ER alpha and ER beta in normal physiology and as therapeutic targets. We synthesized two series of ER ligands, based on a common indene scaffold, in an attempt to develop compounds that can selectively modulate ER-mediated transcription. The 3-ethyl-1,2-diarylindenes, utilizing an amide linker for the 1-aryl extension, bind weakly to the ERs. The 2,3-diarylindenes bind with high affinity to the ER subtypes and demonstrate a range of different biological activities, both in transcriptional reporter gene assays and inhibition of estradiol-stimulated proliferation of MCF-7 cells. Several ligands differentiate between ER alpha and ER beta subtypes at an estrogen response element (ERE), displaying various levels of partial to full agonist activity at ER alpha, while antagonizing estradiol action at ER beta.