2-(5-benzyloxyindole)carboxamide | 133845-43-9

• 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: 2-(5-benzyloxyindole)carboxamide
• 英文别名: 5-(Benzyloxy)-1H-indole-2-carboxamide；5-phenylmethoxy-1H-indole-2-carboxamide
• CAS: 133845-43-9
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: LZVBXGZGXYHGLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  68.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(5-benzyloxyindole)carboxamide 在 钯 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以to give 2-carbamoyl-5-hydroxy-1H-indole which的产率得到5-hydroxyindole-2-carboxamide
  参考文献：
  名称：

  Indole derivatives having anti-angiogenetic activity

  摘要：

  本发明涉及使用公式（I）的化合物制造药物，以抑制和/或逆转和/或缓解血管生成及/或与血管生成相关的任何疾病状态的症状：其中：X，p，q，R1，R2，R3，R4和R5如描述中所定义。本发明还涉及使用公式（I）的化合物作为药物，以及公式（I）的新化合物。本发明还提供了公式（I）的药物组合物和公式（I）的化合物合成方法。

  公开号：

  US07125906B2
• 作为产物：
  描述：

  5-苄氧基-1H-吲哚-2-羧酸甲酯 在 氯化铵 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(5-benzyloxyindole)carboxamide
  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

• Chemical compounds
  申请人：Arnould Jean-Claude

  公开号：US20050159474A1

  公开（公告）日：2005-07-21

  The invention relates to the use of a compound of Formula (I), for the manufacture of a medicament to inhibit and/or reverse and/or alleviate symptoms of angiogenesis and/or any disease state associated with angiogenesis: wherein: X, p, q, R 1 , R 2 , R 3 , R 4 , and R 5 are as defined in the description. The invention also related to use of compounds of Formula (I) as medicaments and also to novel compounds of Formula (I). The invention further provides pharmaceutical compositions of compounds of Formula (I) and processes for the synthesis of compounds of Formula (I).

  本发明涉及使用式（I）的化合物制造药物，以抑制和/或逆转和/或缓解血管生成及/或与血管生成相关的任何疾病状态的症状：其中：X，p，q，R1，R2，R3，R4和R5如说明书中定义的那样。本发明还涉及使用式（I）的化合物作为药物，以及式（I）的新化合物。本发明还提供了式（I）的化合物的制药组合物和合成式（I）的化合物的过程。
• CRUCES, M. A.;ELORRIAGA, C.;FERNANDEZ-ALVAREZ, E., EUR. J. MED. CHEM., 26,(1991) N, C. 33-41
  作者：CRUCES, M. A.、ELORRIAGA, C.、FERNANDEZ-ALVAREZ, E.

  DOI：——

  日期：——
• INDOLE DERIVATIVES HAVING ANTI-ANGIOGENETIC ACTIVITY
  申请人：Astrazeneca AB

  公开号：EP1515716A2

  公开（公告）日：2005-03-23
• US7125906B2
  申请人：——

  公开号：US7125906B2

  公开（公告）日：2006-10-24
• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSES CHIMIQUES
  申请人：ASTRAZENECA AB

  公开号：WO2003082271A2

  公开（公告）日：2003-10-09

  The invention relates to the use of a compound of Formula (I), for the manufacture of a medicament to inhibit and/or reverse and/or alleviate symptoms of angiogenesis and/or any disease state associated with angiogenesis: Formula (I); wherein: X, p, q, R1, R2, R3, R4, and R5 are as defined in the description. The invention also relates to use of compounds of Formula (I) as medicaments and also to novel compounds of Formula (I). The invention further provides pharmaceutical compositions of compounds of Formula (I) and processes for the synthesis of compounds of Formula (I).