羟吲哚-3-乙醛酸乙酯 | 65112-88-1

• 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: 羟吲哚-3-乙醛酸乙酯
• 英文名称: ethyl oxindole-3-glyoxalate
• 英文别名: oxo-(2-oxo-2,3-dihydro-indol-3-yl)-acetic acid ethyl ester；(2-oxo-indolin-3-yl)-glyoxylic acid ethyl ester；(2-Oxo-indolin-3-yl)-glyoxylsaeure-aethylester；Ethyl oxindole-3-glyoxylate；Ethyl oxo(2-oxo-2,3-dihydro-1H-indol-3-yl)acetate；ethyl 2-oxo-2-(2-oxo-1,3-dihydroindol-3-yl)acetate
• CAS: 65112-88-1
• 化学式: C₁₂H₁₁NO₄
• mdl: MFCD00030214
• 分子量: 233.224
• InChiKey: UXGCSFRJKPEYBN-UHFFFAOYSA-N

物化性质

• 熔点：
  187 °C
• 沸点：
  416.3±45.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  羟吲哚-3-乙醛酸乙酯 在 palladium on activated charcoal 、 乙醇 、 硫酸 、 溶剂黄146 作用下， 生成 ethyl 2-(2-oxoindolin-3-yl)acetate
  参考文献：
  名称：

  Studies in the Indole Series. XIII. Oxindole-3-propionic Acid

  摘要：

  DOI：

  10.1021/ja01117a047
• 作为产物：
  描述：

  2-吲哚酮 、 草酸二乙酯 在 乙醚 、 potassium ethoxide 作用下， 生成 羟吲哚-3-乙醛酸乙酯
  参考文献：
  名称：

  Wislicenus; Bubeck, Justus Liebigs Annalen der Chemie, 1924, vol. 436, p. 117

  摘要：

  DOI：

文献信息

• Pyrazolo-quinoline derivatives for treating cerebral ischemia
  申请人：Merck Sharp & Dohme Ltd.

  公开号：US05580877A1

  公开（公告）日：1996-12-03

  A class of 3,5-dihydro-1H-pyrazolo[3,4-c]quinoline-1,4(2H)-dione derivatives, substituted in the 2-position by an optionally substituted phenyl moiety, are selective non-competitive antagonists of NMDA receptors and/or are antagonists of AMPA receptors, and are therefore of utility in the treatment and/or prevention of conditions, such as neurodegenerative disorders, convulsions or schizophrenia, which require the administration of an NMDA and/or AMPA antagonist.

  一类3,5-二氢-1H-吡唑并[3,4-c]喹啉-1,4(2H)-二酮衍生物，其2-位取代为可选取代的苯基基团，是选择性非竞争性NMDA受体拮抗剂和/或AMPA受体拮抗剂，因此在治疗和/或预防需要使用NMDA和/或AMPA拮抗剂的情况下，如神经退行性疾病、惊厥或精神分裂症等方面具有实用价值。
• Horner, Justus Liebigs Annalen der Chemie, 1941, vol. 548, p. 117,140
  作者：Horner

  DOI：——

  日期：——
• Identification of 3,5-Dihydro-2-aryl-1H-pyrazolo[3,4-c]quinoline-1,4(2H)-diones as Novel High-Affinity Glycine Site N-Methyl-D-aspartate Antagonists
  作者：Angus M. MacLeod、Sarah Grimwood、Cheryl Barton、Linda Bristow、Kay L. Saywell、George R. Marshall、Richard G. Ball

  DOI：10.1021/jm00012a024

  日期：1995.6

  Almost all of the exisiting known antagonists at the glycine site of the N-methyl-D-aspartate (NMDA) receptor have a low propensity for crossing the blood-brain barrier. It has been suggested that in many cases this may be due to the presence of a carboxylic acid which is a common feature of most of the potent full antagonists at this receptor. In this study, 2-aryl-1H-pyrazolo[3,4-c]quinoline-1,4(2H)-diones were found to have high-affinity binding at the glycine receptor. In particular, structure-activity studies identified 7-chloro-3,5-dihydro-2(4-methoxyphenyl)-1H-pyrazolo[3,4-c]quinoline-1,4(2H)-dione as the most potent of a series of analogues with an IC50 of 3.3 nM. The measured pK(a) values in this class of compounds (typically 4.0) indicate they are of equivalent acidity to carboxylic acids. Functional antagonism was demonstrated by inhibition of NMDA-evoked responses in rat cortical slices. Anticonvulsant activity in DBA/2 mice was achieved after dosing by direct injection into the cerebral ventricles, but no activity was seen after systemic administration, suggesting low brain penetration with this class of antagonists.
• US5580877A
  申请人：——

  公开号：US5580877A

  公开（公告）日：1996-12-03