4-羟基吲哚酮 | 13402-55-6

• 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-羟基吲哚酮
• 中文别名: 4-羟基-1,3-二氢吲哚-2-酮；4-羟基-2-吲哚酮；4-羟基-1,3-二氢-2H-吲哚-2-酮
• 英文名称: 4-Hydroxy-oxindol
• 英文别名: 4-Hydroxyindolin-2-one；4-hydroxy-1,3-dihydroindol-2-one
• CAS: 13402-55-6
• 化学式: C₈H₇NO₂
• mdl: MFCD03095183
• 分子量: 149.149
• InChiKey: FTJQLPXJRKHATE-UHFFFAOYSA-N

物化性质

• 熔点：
  267 °C(Solv: water (7732-18-5))
• 沸点：
  370.8±42.0 °C(Predicted)
• 密度：
  1.362±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933790090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4-羟基吲哚酮 在 吡啶 、 三氯化铝 作用下， 反应 1.25h， 生成 5-acetyl-1,3-dihydro-4-hydroxy-2H-indol-2-one
  参考文献：
  名称：

  5,7-Dihydro-3-[2-[1-(phenylmethyl)-4-piperidinyl]ethyl]-6H-pyrrolo[3,2-f]-1,2-benzisoxazol-6-one: A Potent and Centrally-Selective Inhibitor of Acetylcholinesterase

  摘要：

  A series of N-benzylpiperidines (2a-d, 10) with novel isoxazole-containing tricycles has been prepared. This series has shown potent in vitro inhibition of the enzyme acetylcholinesterase (AChE), with IC(50)s = 0.33-3.6 nM. Compound 2a was the most potent inhibitor with an IC50 = 0.33 +/- 0.09 nM. Derivatives 2a-d and 10 displayed weak in vitro inhibition of butyrylcholinesterase (BuChE) with IC(50)s = 600-23 000 nM. The most selective compound was 2a with a BuChE/AChE ratio in excess of 4 orders of magnitude (>10 000). Pyrrolobenzisoxazole 2a also displayed a favorable profile in vivo. In microdialysis experiments, 2a produced a 200% increase in extracellular levels of acetylcholine (ACh) at a dose of 0.4 mg/kg in freely moving, conscious rats. Peripheral side effects (salivation ED(50) = 26 +/- 1.5 mg/kg) and acute lethality (LD(50)[1 h] = 42 mg/kg) were observed at >60-fold higher doses. These data indicate that 2a is an AChE inhibitor with good central selectivity and a favorable margin of safety. Compound 2a, designated as CP-118,954, is currently in clinical development for the treatment of cognitive disorders.

  DOI：

  10.1021/jm00015a002
• 作为产物：
  描述：

  (2-甲氧基-6-硝基苯基)乙腈 在 palladium on activated charcoal 盐酸 、 硫酸 、 氢溴酸 、 氢气 作用下， 生成 4-羟基吲哚酮
  参考文献：
  名称：

  Novel substituted 4-aminomethylpiperidines as potent and selective human β3-agonists. Part 1: aryloxypropanolaminomethylpiperidines

  摘要：

  The synthesis and SAR of a series of human beta(3) adrenoreceptor agonists based on a template derived from a common pharmacophore coupled with 4-aminomethylpiperidine is described. Potent and selective agents were identified such as 26 that was in vitro active in CHO cells expressing human beta(3)-AR (EC50 = 49 nNl, IA = 1.1), and in vivo active in a transgenic mouse model. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00607-8

文献信息

• FUSED HETEROCYCLIC COMPOUND
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2103620A1

  公开（公告）日：2009-09-23

  The present invention provides a fused heterocyclic compound having a tyrosine kinase inhibitory action, which is represented by the formula: wherein R1 is a hydrogen atom, a halogen atom, or an optionally substituted group bonded via a carbon atom, a nitrogen atom or an oxygen atom; R2 is a hydrogen atom, or an optionally substituted group bonded via a carbon atom or a sulfur atom, or R1 and R2, or R2 and R3 are optionally bonded to each other to form an optionally substituted ring structure; R3 is a hydrogen atom or an optionally substituted aliphatic hydrocarbon group, or R3 is optionally bonded to the carbon atom on ring A to form an optionally substituted ring structure; ring A is an optionally substituted benzene ring; and ring B is (i) an optionally substituted fused ring, or (ii) a pyridine ring having optionally substituted carbamoyl (the pyridine ring is optionally further substituted).

  本发明提供了一种具有酪氨酸激酶抑制作用的融合杂环化合物，其化学式如下： 其中 R1是氢原子、卤素原子或通过碳原子、氮原子或氧原子键合的可选择取代基； R2是氢原子，或通过碳原子或硫原子键合的可选择取代基，或 R1和R2，或R2和R3可选择键合在一起形成可选择取代的环结构； R3是氢原子或可选择取代的脂肪烃基，或 R3可选择键合到环A上的碳原子上形成可选择取代的环结构； 环A是可选择取代的苯环；环B是 (i) 可选择取代的融合环，或 (ii) 具有可选择取代的氨基甲酰基的吡啶环（吡啶环可进一步取代）。
• Substituted 2- (S) -hydroxy-3- (piperidin-4-yl-methylamino) -propyl ethers and substituted 2-aryl-2- (R) - hydroxy-1- (piperidin-4-yl-methyl) -ethylamine beta-3 adrenergic receptor agonists
  申请人：American Home Products Corporation

  公开号：US20020037907A1

  公开（公告）日：2002-03-28

  This invention provides compounds of Formula I having the structure 1 wherein A, B, Z, R and R 1 are as defined hereinbefore, or a pharmaceutically acceptable salt thereof, which are useful in treating or inhibiting metabolic disorders related to insulin resistance or hyperglycemia (typically associated with obesity or glucose intolerance), atherosclerosis, gastrointestinal disorders, neurogenetic inflammation, glaucoma, ocular hypertension and frequent urination; and are particularly useful in the treatment or inhibition of type II diabetes.

  这项发明提供了具有结构式1的化合物，其中A、B、Z、R和R1如前文所定义，或其药学上可接受的盐，用于治疗或抑制与胰岛素抵抗或高血糖相关的代谢紊乱（通常与肥胖或葡萄糖不耐受有关）、动脉粥样硬化、胃肠道疾病、神经炎症、青光眼、眼压增高和频繁排尿；特别适用于治疗或抑制2型糖尿病。
• 3,3-dialkyl-and 3,3-alkylene-indoline derivatives, processes for their
  申请人：Sandoz Ltd.

  公开号：US04622336A1

  公开（公告）日：1986-11-11

  3,3-Dialkyl- or 3,3-alkylene-indolines which are unsubstituted at the 1- and 2-positions and which are substituted at the 4- or 6-position by an optionally etherified hydroxy group or substituted at the 5- or 7-position by an etherified hydroxy group, as well as their physiologically-hydrolyzable and -acceptable esters. The said indolines and esters as well as their pharmaceutically acceptable acid addition salts possess analgesic activity.

  3,3-二烷基-或3,3-烷基烯基-吲哚啉，其在1-和2-位置未取代，在4-或6-位置被一羟基可选地醚化取代，或在5-或7-位置被一醚化羟基取代，以及它们的生理可水解和可接受的酯。所述的吲哚啉和酯以及它们的药用可接受的酸盐具有镇痛活性。
• 3-Substituted oxindole beta 3 agonists
  申请人：——

  公开号：US20040097532A1

  公开（公告）日：2004-05-20

  The present invention relates to a &bgr;;3 adrenergic receptor agonist of formula I: (I); or a pharmaceutical salt thereof; which is useful for treating Type II diabetes and/or obesity.

  本发明涉及一种公式I的&bgr;;3肾上腺素受体激动剂：(I)或其药物盐；其可用于治疗II型糖尿病和/或肥胖症。
• 3-Substituted oxindole beta3 agonists
  申请人：Jesudason Darshini Cynthia

  公开号：US20050054713A1

  公开（公告）日：2005-03-10

  The present invention relates to a β 3 adrenergic receptor agonist of formula I: or a pharmaceutical salt thereof; which is useful for treating Type II diabetes and/or obesity.

  本发明涉及一种式I的β3肾上腺素受体激动剂或其药用盐；其可用于治疗II型糖尿病和/或肥胖症。