2-[5-chloro-3-(nitromethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]acetamide | 916047-92-2

• 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-chloro-3-(nitromethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]acetamide
• 英文别名: 2-[5-chloro-3-(nitromethyl)-2-oxo-1H-indol-3-yl]acetamide
• CAS: 916047-92-2
• 化学式: C₁₁H₁₀ClN₃O₄
• 分子量: 283.671
• InChiKey: PXKWKXKHKUYZBH-UHFFFAOYSA-N

物化性质

• 沸点：
  640.1±55.0 °C(Predicted)
• 密度：
  1.464±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[5-chloro-3-(nitromethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]acetamide 在 溶剂黄146 、 锌 作用下， 反应 3.0h， 生成 5-chloro-5'H-spiro[indole-3,3'-pyrrolidine]-2,5'(1H)-dione
  参考文献：
  名称：

  Discovery of a New Class of Potent, Selective, and Orally Bioavailable CRTH2 (DP2) Receptor Antagonists for the Treatment of Allergic Inflammatory Diseases

  摘要：

  A novel chemical class of potent chemoattractant receptor-homologous expressed on Th2 lymphocytes (CRTH2 or DP2) antagonists is reported. An initial and moderately potent spiro-indolinone compound (5) was found during a high-throughput screening campaign. Structure - activity relationship (SAR) investigation around the carboxylic acid group revealed that changes in this part of the molecule could lead to a reversal of functional activity, yielding weakly potent agonists. SAR investigation of the succinimide functional group led to the discovery of several single-digit nanomolar antagonists. The potency of these compounds was confirmed in a human eosinophil chemotaxis assay. Moreover, compounds (R)-58 and (R)-71 were shown to possess pharmacokinetic properties suitable for development as an orally bioavailable drug.

  DOI：

  10.1021/jm701383e
• 作为产物：
  描述：

  (5-chloro-3-(nitromethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl)acetonitrile 在 palladium dichloride 乙酰胺 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 2-[5-chloro-3-(nitromethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]acetamide
  参考文献：
  名称：

  WO2006/125784

  摘要：

  公开号：

文献信息

• Tricyclic spiro derivatives as CRTH2 modulators
  申请人：Schwarz Matthias

  公开号：US20090318486A1

  公开（公告）日：2009-12-24

  The present invention is related to the use of spiro derivatives of Formula (I) for the treatment and/or prevention of allergic diseases, inflammatory dermatoses and other diseases with an inflammatory component. Specifically, the present invention is related to the use of spiro derivatives for the modulation of CRTH2 activity.

  本发明涉及使用式(I)的螺环衍生物用于治疗和/或预防过敏性疾病、炎症性皮肤病和其他具有炎症成分的疾病。具体而言，本发明涉及使用螺环衍生物来调节CRTH2活性。
• TRICYCLIC SPIRO DERIVATIVES AS CRTH2 MODULATORS
  申请人：LABORATOIRES SERONO S.A.

  公开号：EP1891075A1

  公开（公告）日：2008-02-27
• US8236963B2
  申请人：——

  公开号：US8236963B2

  公开（公告）日：2012-08-07
• [EN] TRICYCLIC SPIRO DERIVATIVES AS CRTH2 MODULATORS<br/>[FR] DERIVES SPIRO TRICYCLIQUES SERVANT DE MODULATEURS DE CRTH2
  申请人：APPLIED RESEARCH SYSTEMS

  公开号：WO2006125784A1

  公开（公告）日：2006-11-30

  [EN] The present invention is related to the use of spiro derivatives of Formula (I) for the treatment and/or prevention of allergic diseases, inflammatory dermatoses and other diseases with an inflammatory component. Specifically, the present invention is related to the use of spiro derivatives for the modulation of CRTH2 activity.
  [FR] L'invention concerne l'utilisation de dérivés spiro de formule (I) pour traiter et/ou pour prévenir des maladies allergiques, des dermatoses inflammatoires et d'autres maladies présentant une composante inflammatoire. En particulier, l'invention concerne l'utilisation de dérivés spiro pour moduler l'activité de CRTH2.
• WO2006/125784
  申请人：——

  公开号：——

  公开（公告）日：——