4-氯-1-甲基-1H-吲哚-2-羧酸乙酯 | 1026657-34-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 4-氯-1-甲基-1H-吲哚-2-羧酸乙酯
• 英文名称: Ethyl 4-chloro-1-methylindole-2-carboxylate
• CAS: 1026657-34-0
• 化学式: C₁₂H₁₂ClNO₂
• 分子量: 237.686
• InChiKey: GZOCOVXJKLWMAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-氯-1-甲基-1H-吲哚-2-羧酸乙酯 在 三甲基铝 作用下， 生成 4-chloro-2-(4,5-dihydro-1H-imidazol-2-yl)-1-methyl-2,3-dihydroindole
  参考文献：
  名称：

  Indoline analogs of idazoxan: potent .alpha.2-antagonists and .alpha.1-agonists

  摘要：

  The synthesis and alpha-adrenergic activity of a series of substituted 2-imidazolinylindolines are described. Substitution in the indoline ring generated compounds with a spectrum of adrenoceptor antagonist/agonist profiles that proved sensitive to both the nature and position of the substituent. Many of the derivatives possess greater presynaptic antagonist potency than the corresponding benzodioxan 1, dihydrobenzofuran 2, and indan 3 analogues; however, this alpha 2-antagonism is often accompanied by alpha 1-agonist activity. It was not possible to separate alpha 2-antagonist from alpha 1-agonist properties in this series. Compounds of most interest proved to be the N-ethyl 6, 5-chloro-N-methyl 18, and 5-chloro-N-ethyl 23 derivatives, all being potent alpha 2-antagonists and alpha 1-agonists. Substitution at the 4- and 7-position of the indoline ring generally gave compounds with nonselective agonist properties.

  DOI：

  10.1021/jm00400a009
• 作为产物：
  描述：

  4-氯吲哚-2-甲酸 在 硫酸 作用下， 生成 4-氯-1-甲基-1H-吲哚-2-羧酸乙酯
  参考文献：
  名称：

  Indoline analogs of idazoxan: potent .alpha.2-antagonists and .alpha.1-agonists

  摘要：

  The synthesis and alpha-adrenergic activity of a series of substituted 2-imidazolinylindolines are described. Substitution in the indoline ring generated compounds with a spectrum of adrenoceptor antagonist/agonist profiles that proved sensitive to both the nature and position of the substituent. Many of the derivatives possess greater presynaptic antagonist potency than the corresponding benzodioxan 1, dihydrobenzofuran 2, and indan 3 analogues; however, this alpha 2-antagonism is often accompanied by alpha 1-agonist activity. It was not possible to separate alpha 2-antagonist from alpha 1-agonist properties in this series. Compounds of most interest proved to be the N-ethyl 6, 5-chloro-N-methyl 18, and 5-chloro-N-ethyl 23 derivatives, all being potent alpha 2-antagonists and alpha 1-agonists. Substitution at the 4- and 7-position of the indoline ring generally gave compounds with nonselective agonist properties.

  DOI：

  10.1021/jm00400a009

文献信息

• Synthesis, Biological Evaluation, and Structure−Activity Relationships of 3-Acylindole-2-carboxylic Acids as Inhibitors of the Cytosolic Phospholipase A₂
  作者：Matthias Lehr

  DOI：10.1021/jm960863w

  日期：1997.8.1

  Replacement of the carboxylic acid group in position 2 of the indole with an acetic or propionic acid substituent led to a decrease of inhibitory potency. Enzyme inhibition was optimal when the acyl residue in position 3 had a length of 12 or more carbons. Conformational restriction of the acyl residue did not influence activity. Introduction of alkyl chains at position 1 of the indole with 8 or more carbons

  制备3-酰基吲哚-2-羧酸衍生物，并评价其抑制完整牛血小板的胞质磷脂酶A2的能力。为了定义酶抑制的结构要求，对羧酸基，酰基残基和位置1的部分进行了系统修饰。此外，将不同的取代基引入到吲哚的苯基部分中。用乙酸或丙酸取代基取代吲哚的2位上的羧酸基导致抑制效力的降低。当位置3上的酰基残基具有12个或更多碳原子时，酶抑制作用最佳。酰基残基的构象限制不影响活性。在具有8个或更多个碳的吲哚的位置1处引入烷基链导致活性降低。然而，发现用羧酸部分取代此类化合物的ω-甲基会显着增加抑制效力。在测试的吲哚衍生物中，1- [2-（4-羧基苯氧基）乙基] -3-十二烷酰基吲哚-2-羧基酸（29b）具有最高的效价。IC50为0.5 microM，它的活性比标准cPLA2抑制剂花生四烯酸三氟甲基酮（IC50：11 microM）高约20倍。
• FAGAN, GAY P.;CHAPLEO, CHRISTOPHER B.;LANE, ANTHONY C.;MYERS, MALCOLM;ROA+, J. MED. CHEM., 31,(1988) N 5, 944-948
  作者：FAGAN, GAY P.、CHAPLEO, CHRISTOPHER B.、LANE, ANTHONY C.、MYERS, MALCOLM、ROA+

  DOI：——

  日期：——