methyl 4-[2-(1-benzhydryl-2-{2-[(benzylsulfonyl)amino]ethyl}-5-chloro-1H-indol-3-yl)ethoxy]benzoate | 683812-86-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-[2-(1-benzhydryl-2-{2-[(benzylsulfonyl)amino]ethyl}-5-chloro-1H-indol-3-yl)ethoxy]benzoate
• 英文别名: Methyl 4-[2-[1-benzhydryl-2-[2-(benzylsulfonylamino)ethyl]-5-chloroindol-3-yl]ethoxy]benzoate
• CAS: 683812-86-4
• 化学式: C₄₀H₃₇ClN₂O₅S
• 分子量: 693.263
• InChiKey: UPALOYIRPXDBDM-UHFFFAOYSA-N

物化性质

• 沸点：
  853.4±75.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  49
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  95
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4-[2-(1-benzhydryl-2-{2-[(benzylsulfonyl)amino]ethyl}-5-chloro-1H-indol-3-yl)ethoxy]benzoate 在 sodium hydroxide 、 silver(l) oxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 4-[2-(1-benzhydryl-2-{2-[(benzylsulfonyl)(methyl)amino]ethyl}-5-chloro-1H-indol-3-yl)ethoxy]benzoic acid
  参考文献：
  名称：

  Discovery of Ecopladib, an Indole Inhibitor of Cytosolic Phospholipase Α₂α

  摘要：

  The synthesis and structure-activity relationship of a series of indole inhibitors of cytosolic phospholipase A(2)alpha (cPLA(2)alpha, type IVA phospholipase) are described. Inhibitors of cPLA(2)alpha are predicted to be efficacious in treating asthma as well as the signs and symptoms of osteoarthritis, rheumatoid arthritis, and pain. The introduction of a benzyl sulfonamide substituent at C2 was found to impart improved potency of these inhibitors, and the SAR of these sulfonamide analogues is disclosed. Compound 123 (Ecopladib) is a sub-micromolar inhibitor of cPLA(2)alpha in the GLU micelle and rat whole blood assays. Compound 123 displayed oral efficacy in the rat carrageenan air pouch and rat carrageenan-induced paw edema models.

  DOI：

  10.1021/jm061131z
• 作为产物：
  描述：

  methyl 4-[2-[5-chloro-(1-diphenylmethyl)-2-methyl-1H-indol-3-yl]ethoxy]benzoate 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 ammonium acetate 、 水 、 碳酸氢钠 、 silver carbonate 、 汞 、 锌 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 丙酮 为溶剂， 反应 8.5h， 生成 methyl 4-[2-(1-benzhydryl-2-{2-[(benzylsulfonyl)amino]ethyl}-5-chloro-1H-indol-3-yl)ethoxy]benzoate
  参考文献：
  名称：

  Discovery of Ecopladib, an Indole Inhibitor of Cytosolic Phospholipase Α₂α

  摘要：

  The synthesis and structure-activity relationship of a series of indole inhibitors of cytosolic phospholipase A(2)alpha (cPLA(2)alpha, type IVA phospholipase) are described. Inhibitors of cPLA(2)alpha are predicted to be efficacious in treating asthma as well as the signs and symptoms of osteoarthritis, rheumatoid arthritis, and pain. The introduction of a benzyl sulfonamide substituent at C2 was found to impart improved potency of these inhibitors, and the SAR of these sulfonamide analogues is disclosed. Compound 123 (Ecopladib) is a sub-micromolar inhibitor of cPLA(2)alpha in the GLU micelle and rat whole blood assays. Compound 123 displayed oral efficacy in the rat carrageenan air pouch and rat carrageenan-induced paw edema models.

  DOI：

  10.1021/jm061131z

文献信息

• Methods for the use of inhibitors of cytosolic phospholipase A2 in the treatment of thrombosis
  申请人：Clerin Valerie

  公开号：US20080009485A1

  公开（公告）日：2008-01-10

  This invention provides methods for the use of substituted indole compounds of the general formula: and pharmaceutically acceptable salt forms thereof. The invention provides methods for the use of the compounds in the treating or preventing thrombosis in a mammal, or preventing progression of symptoms of thrombosis.

  这项发明提供了一种使用通式所示的取代吲哚化合物及其药用盐形式的方法。该发明提供了一种在哺乳动物中治疗或预防血栓形成，或预防血栓形成症状进展的化合物使用方法。
• Process for making an aldehyde
  申请人：Wyeth

  公开号：US20040082785A1

  公开（公告）日：2004-04-29

  A process for making an aromatic aldehyde in which a sulfoxide is reacted with a dihalogenated aromatic compound in the absence of an effective amount of an activating reagent. The aldehyde may then be used to make other compounds, such as a compound that acts as a cPLA inhibitor.

  一种制备芳香醛的过程，其中亚砜与双卤代芳香化合物在缺乏有效量活化试剂的情况下发生反应。然后可以使用该醛制备其他化合物，例如作为cPLA抑制剂的化合物。