Ethyl 3-[5-(2-amino-2-oxoethoxy)-3-tert-butylsulfanyl-1-[(4-chlorophenyl)methyl]indol-2-yl]-2,2-dimethylpropanoate | 950700-55-7

• 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: Ethyl 3-[5-(2-amino-2-oxoethoxy)-3-tert-butylsulfanyl-1-[(4-chlorophenyl)methyl]indol-2-yl]-2,2-dimethylpropanoate
• CAS: 950700-55-7
• 化学式: C₂₈H₃₅ClN₂O₄S
• 分子量: 531.116
• InChiKey: DTZDVWMJEWSAHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 3-[5-(2-amino-2-oxoethoxy)-3-tert-butylsulfanyl-1-[(4-chlorophenyl)methyl]indol-2-yl]-2,2-dimethylpropanoate 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 3-(5-(2-amino-2-oxoethoxy)-3-(tert-butylthio)-1-(4-chlorobenzyl)-1H-indol-2-yl)-2,2-dimethylpropanoic acid
  参考文献：
  名称：

  5-Lipoxygenase-activating protein inhibitors. Part 2: 3-{5-((S)-1-Acetyl-2,3-dihydro-1H-indol-2-ylmethoxy)-3-tert-butylsulfanyl-1-[4-(5-methoxy-pyrimidin-2-yl)-benzyl]-1H-indol-2-yl}-2,2-dimethyl-propionic acid (AM679)—A potent FLAP inhibitor

  摘要：

  A series of potent 5-lipoxygenase-activating protein (FLAP) inhibitors are herein described. SAR studies focused on the discovery of novel alicyclic moieties appended to an indole core to optimize potency, physical properties and off-target activities. Subsequent SAR on the N-benzyl substituent of the indole led to the discovery of compound 39 (AM679) which showed potent inhibition of leukotrienes in human blood and in a rodent bronchoalvelolar lavage (BAL) challenge model. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.131
• 作为产物：
  描述：

  2-溴乙酰胺 、 1-[(4-氯苯基)甲基]-3-[(1,1-二甲基乙基)硫基]-5-羟基-alpha,alpha-二甲基-1H-吲哚-2-丙酸乙酯 在 caesium carbonate 作用下， 生成 Ethyl 3-[5-(2-amino-2-oxoethoxy)-3-tert-butylsulfanyl-1-[(4-chlorophenyl)methyl]indol-2-yl]-2,2-dimethylpropanoate
  参考文献：
  名称：

  5-Lipoxygenase-activating protein inhibitors. Part 2: 3-{5-((S)-1-Acetyl-2,3-dihydro-1H-indol-2-ylmethoxy)-3-tert-butylsulfanyl-1-[4-(5-methoxy-pyrimidin-2-yl)-benzyl]-1H-indol-2-yl}-2,2-dimethyl-propionic acid (AM679)—A potent FLAP inhibitor

  摘要：

  A series of potent 5-lipoxygenase-activating protein (FLAP) inhibitors are herein described. SAR studies focused on the discovery of novel alicyclic moieties appended to an indole core to optimize potency, physical properties and off-target activities. Subsequent SAR on the N-benzyl substituent of the indole led to the discovery of compound 39 (AM679) which showed potent inhibition of leukotrienes in human blood and in a rodent bronchoalvelolar lavage (BAL) challenge model. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.131

文献信息

• 5-LIPOXYGENASE-ACTIVATING PROTEIN (FLAP) INHIBITORS
  申请人：Hutchinson Howard John

  公开号：US20070219206A1

  公开（公告）日：2007-09-20

  Described herein are compounds and pharmaceutical compositions containing such compounds, which modulate the activity of 5-lipoxygenase-activating protein (FLAP). Also described herein are methods of using such FLAP modulators, alone and in combination with other compounds, for treating respiratory, cardiovascular, and other leukotriene-dependent or leukotriene mediated conditions or diseases.

  本文描述了一些化合物和含有这些化合物的制药组合物，这些化合物可以调节5-脂氧合酶激活蛋白（FLAP）的活性。本文还描述了使用这种FLAP调节剂的方法，单独或与其他化合物结合，用于治疗呼吸系统、心血管系统和其他依赖于白三烯或介导白三烯的疾病或病症。
• 5-Lipoxygenase-Activating Protein (FLAP) Inhibitors
  申请人：Hutchinson John Howard

  公开号：US20110034514A1

  公开（公告）日：2011-02-10

  Described herein are compounds and pharmaceutical compositions containing such compounds, which modulate the activity of 5-lipoxygenase-activating protein (FLAP). Also described herein are methods of using such FLAP modulators, alone and in combination with other compounds, for treating respiratory, cardiovascular, and other leukotriene-dependent or leukotriene mediated conditions or diseases.

  本文描述了含有这些化合物的药物组合物，这些化合物可以调节5-脂氧合酶激活蛋白（FLAP）的活性。本文还描述了使用这些FLAP调节剂的方法，单独或与其他化合物组合，用于治疗呼吸系统、心血管系统和其他依赖或介导白三烯的疾病或病症。
• US7834037B2
  申请人：——

  公开号：US7834037B2

  公开（公告）日：2010-11-16
• [EN] 5-LIPOXYGENASE-ACTIVATING PROTEIN (FLAP) INHIBITORS<br/>[FR] INHIBITEURS DE LA PROTEINE D'ACTIVATION DE LA 5-LIPOXYGENASE (FLAP)
  申请人：AMIRA PHARMACEUTICALS INC

  公开号：WO2007056228A2

  公开（公告）日：2007-05-18

  [EN] Described herein are compounds and pharmaceutical compositions containing such compounds, which modulate the activity of 5-lipoxygenase-activating protein (FLAP). Also described herein are methods of using such FLAP modulators, alone and in combination with other compounds, for treating respiratory, cardiovascular, and other leukotriene-dependent or leukotriene mediated conditions or diseases.
  [FR] L'invention concerne des composés et des compositions pharmaceutiques contenant de tels composés, qui permettent de moduler l'activité de la protéine d'activation de la 5-lipoxygénase (FLAP). Cette invention a aussi pour objet des méthodes d'utilisation de modulateurs de cette protéine d'activation de la 5-lipoxygénase (FLAP), seuls et en combinaison avec d'autres composés, dans le traitement de troubles ou de maladies respiratoires, cardio-vasculaires et dépendants de la leukotriène ou médiés par la leukotriène.