5-苯氧基-2-羧基吲哚 | 78304-52-6

• 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: 5-苯氧基-2-羧基吲哚
• 中文别名: 5-苯氧基-1H-吲哚-2-羧酸
• 英文名称: 5-phenoxy-2-carboxyindole
• 英文别名: 5-phenoxy-1H-indole-2-carboxylic acid
• CAS: 78304-52-6
• 化学式: C₁₅H₁₁NO₃
• 分子量: 253.257
• InChiKey: KIVFYFCCEIOXCO-UHFFFAOYSA-N

物化性质

• 溶解度：
  >38 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-苯氧基-2-羧基吲哚 反应 0.17h， 以40%的产率得到5-苯氧基-1H-吲哚
  参考文献：
  名称：

  Diindolyls. 8. Synthesis of di(5-indolyl) oxide

  摘要：

  DOI：

  10.1007/bf00507090
• 作为产物：
  描述：

  4-苯氧基苯肼 在 sodium acetate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 5-苯氧基-2-羧基吲哚
  参考文献：
  名称：

  Structure-based design and biological evaluation of novel 2-(indol-2-yl) thiazole derivatives as xanthine oxidase inhibitors

  摘要：

  Inhibition of xanthine oxidase (XO) has obviously been a central concept for controlling hyperuricemia, which causes serious and painful inflammatory arthritis disease such as gout. We discovered a series of novel 2-(indol-2-yl) thiazole derivatives as XO inhibitors at the level of nanomolar activity. Structure-guided design using molecular modeling program (Accelrys Software program) provided an excellent basis for optimization of 2-(indol-2-yl) thiazole compounds. Structure-activity relationship indicated that hydrophobic alkoxy group (isopropoxy, cyclopentoxy) at 5-position and hydrogen binding acceptor (NO2, CN) at 7-position of indole ring appear as critical functional groups. Among the compounds, 2-(7-nitro-5-isopropoxy- indol-2-yl)-4-methylthiazole-5-carboxylic acid (9m) exhibits the most potent XO inhibitory activity (IC50 value: 5.1 nM) and the excellent uric acid lowering activity in potassium oxonate induced hyperuricemic rat model. (C) 2016 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2015.12.055

文献信息

• [EN] INDOLE COMPOUND<br/>[FR] COMPOSÉ INDOLE
  申请人：ASTELLAS PHARMA INC

  公开号：WO2010101127A1

  公开（公告）日：2010-09-10

  【課題】本発明の課題は、医薬組成物、例えば１７βＨＳＤ　ｔｙｐｅ　５の関与する疾患の治療剤として有用な化合物の提供である。 【解決手段】本発明者らは、１７βＨＳＤ　ｔｙｐｅ　５の関与する疾患の治療剤として有用な化合物について鋭意検討した結果、２位に置換カルバモイル基を有するインドール化合物が、強力な１７βＨＳＤ　ｔｙｐｅ　５阻害活性を有すること、並びに、テストステロン減少による副作用を伴わない、前立腺肥大症及び前立腺癌等の１７βＨＳＤ　ｔｙｐｅ　５の関与する疾患の治療剤及び／又は予防剤となりうることを知見して本発明を完成した。
• Structure-based design and biological evaluation of novel 2-(indol-2-yl) thiazole derivatives as xanthine oxidase inhibitors
  作者：Jeong Uk Song、Jae Wan Jang、Tae Hun Kim、Heuisul Park、Wan Su Park、Sang-Hun Jung、Geun Tae Kim

  DOI：10.1016/j.bmcl.2015.12.055

  日期：2016.2

  Inhibition of xanthine oxidase (XO) has obviously been a central concept for controlling hyperuricemia, which causes serious and painful inflammatory arthritis disease such as gout. We discovered a series of novel 2-(indol-2-yl) thiazole derivatives as XO inhibitors at the level of nanomolar activity. Structure-guided design using molecular modeling program (Accelrys Software program) provided an excellent basis for optimization of 2-(indol-2-yl) thiazole compounds. Structure-activity relationship indicated that hydrophobic alkoxy group (isopropoxy, cyclopentoxy) at 5-position and hydrogen binding acceptor (NO2, CN) at 7-position of indole ring appear as critical functional groups. Among the compounds, 2-(7-nitro-5-isopropoxy- indol-2-yl)-4-methylthiazole-5-carboxylic acid (9m) exhibits the most potent XO inhibitory activity (IC50 value: 5.1 nM) and the excellent uric acid lowering activity in potassium oxonate induced hyperuricemic rat model. (C) 2016 Published by Elsevier Ltd.
• Diindolyls. 8. Synthesis of di(5-indolyl) oxide
  作者：Sh. A. Samsoniya、D. M. Tabidze、N. N. Suvorov

  DOI：10.1007/bf00507090

  日期：1981.1