methyl [5-chloro-2-(4-methoxypyridine-2-carbonyl)-1H-indol-3-yl]acetate | 231293-08-6

• 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
• 英文名称: methyl [5-chloro-2-(4-methoxypyridine-2-carbonyl)-1H-indol-3-yl]acetate
• 英文别名: Methyl[5-chloro-2-(4-methoxypyridine-2-carbonyl)-1h-indol-3-yl]acetate；methyl 2-[5-chloro-2-(4-methoxypyridine-2-carbonyl)-1H-indol-3-yl]acetate
• CAS: 231293-08-6
• 化学式: C₁₈H₁₅ClN₂O₄
• 分子量: 358.781
• InChiKey: QSXVQLOWMJUHFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  81.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl [5-chloro-2-(4-methoxypyridine-2-carbonyl)-1H-indol-3-yl]acetate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 [5-chloro-2-(4-methoxypyridine-2-carbonyl)-1H-indol-3-yl]acetic acid
  参考文献：
  名称：

  Synthesis of 2-acylindole-3-acetic acids: a novel base-mediated indole synthesis

  摘要：

  An efficient and expedient synthetic route to 2-acylindole-3-acetic acids is described. This work first demonstrates a one-pot room-temperature indole ring construction via the in situ generation of indoline intermediate. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01879-3
• 作为产物：
  描述：

  5-氯-2-硝基苯甲醛 在 吡啶 、 铁粉 、 potassium carbonate 、 氯化铵 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 9.0h， 生成 methyl [5-chloro-2-(4-methoxypyridine-2-carbonyl)-1H-indol-3-yl]acetate
  参考文献：
  名称：

  Synthesis of 2-acylindole-3-acetic acids: a novel base-mediated indole synthesis

  摘要：

  An efficient and expedient synthetic route to 2-acylindole-3-acetic acids is described. This work first demonstrates a one-pot room-temperature indole ring construction via the in situ generation of indoline intermediate. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01879-3

文献信息

• 2,3-substituted indole compounds as anti-inflammatory and analgesic agents
  申请人：——

  公开号：US06608070B1

  公开（公告）日：2003-08-19

  This invention provides a compound of the following formula: or the pharmaceutically acceptable salts thereof wherein Z is OH, C1-6 alkoxy, —NR2R3 or heterocycle; Q is selected from the following: (a) an optionally substituted phenyl, (b) an optionally substituted 6-membered monocyclic aromatic group containing one, two, three or four nitrogen atom(s), (c) an optionally substituted 5-membered monocyclic aromatic group containing one heteroatom selected from O, S and N and optionally containing one, two or three nitrogen atom(s) in addition to said heteroatom, (d) an optionally substituted C3-7 cycloalkyl and (e) an optionally substituted benzo-fuzed heterocycle; R1 is hydrogen, C1-4 alkyl or halo; R2 and R3 are independently hydrogen, OH, C1-4 alkoxy, C1-4 alkyl or C1-4 alkyl substituted with halo, OH, C1-4 alkoxy or CN; X is independently selected from H, halo, C1-4 alkyl, halo-substituted C1-4 alkyl, OH, C1-4 alkoxy, halo-substituted C1-4 alkoxy, C1-4 alkylthio, NO2, NH2, di-(C1-4 alkyl)amino and CN; and n is 0, 1, 2, 3 and 4. This invention also provides a pharmaceutical composition useful for the treatment of a medical condition in which prostaglandins are implicated as pathogens.

  本发明提供以下公式的化合物或其药学上可接受的盐，其中Z为OH、C1-6烷氧基、—NR2R3或杂环；Q从以下选择：（a）可选择取代的苯基，（b）可选择取代的含有一、两、三或四个氮原子的6元单环芳基，（c）可选择取代的含有O、S和N中的一种杂原子的5元单环芳基，并且除了所述杂原子外，还可以选择含有一、两或三个氮原子，（d）可选择取代的C3-7环烷基和（e）可选择取代的苯并杂环；R1为氢、C1-4烷基或卤素；R2和R3分别为氢、OH、C1-4烷氧基、取代有卤素、OH、C1-4烷氧基或CN的C1-4烷基；X独立选择自H、卤素、C1-4烷基、取代有卤素的C1-4烷基、OH、C1-4烷氧基、取代有卤素的C1-4烷氧基、C1-4烷基硫、NO2、NH2、双（C1-4烷基）氨基和CN；n为0、1、2、3和4。本发明还提供一种治疗前列腺素作为病原体的医疗条件的药物组合物。
• Synthesis of 2-acylindole-3-acetic acids: a novel base-mediated indole synthesis
  作者：Kazunari Nakao、Yoshinori Murata、Hiroki Koike、Chikara Uchida、Kiyoshi Kawamura、Sachiko Mihara、Shigeo Hayashi、Rodney W. Stevens

  DOI：10.1016/s0040-4039(03)01879-3

  日期：2003.9

  An efficient and expedient synthetic route to 2-acylindole-3-acetic acids is described. This work first demonstrates a one-pot room-temperature indole ring construction via the in situ generation of indoline intermediate. (C) 2003 Elsevier Ltd. All rights reserved.