1-(4-bromophenyl)-1,3-dihydro-3,3-dimethyl-2H-pyrrolo[2,3-b]pyridin-2-one | 127555-32-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 1-(4-bromophenyl)-1,3-dihydro-3,3-dimethyl-2H-pyrrolo[2,3-b]pyridin-2-one
• 英文别名: 1-(4-Bromophenyl)-3,3-dimethylpyrrolo[2,3-b]pyridin-2-one
• CAS: 127555-32-2
• 化学式: C₁₅H₁₃BrN₂O
• 分子量: 317.185
• InChiKey: MDKQPRLVLXGHEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (4-Bromo-phenyl)-(3-chloromethyl-pyridin-2-yl)-amine; hydrochloride 在 sodium hydroxide 、 正丁基锂 、 三甲基氯硅烷 、 sodium hydride 、 锌 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 78.5h， 生成 1-(4-bromophenyl)-1,3-dihydro-3,3-dimethyl-2H-pyrrolo[2,3-b]pyridin-2-one
  参考文献：
  名称：

  Substituted 1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-ones as potential antiinflammatory agents

  摘要：

  A series of analogues based on the 1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one ring system have been synthesized and shown to possess oral antiinflammatory activity in both the reverse passive Arthus reaction (RPAR) pleural cavity assay in rats and in the adjuvant-induced arthritic rat model (AAR). Several members of this series additionally exhibit an inhibitory effect on the in vivo production of prostaglandin- and leukotriene-derived products or arachidonic acid metabolism although these compounds exhibit no significant inhibitory activity against the cyclooxygenase and 5-lipoxygenase enzymes in vitro. Structure-activity relationships in this series are discussed.

  DOI：

  10.1021/jm00172a004

文献信息

• TING, PAULINE C.;KAMINSKI, JAMES J.;SHERLOCK, MARGARET H.;TOM, WING C.;LE+, J. MED. CHEM., 33,(1990) N0, C. 2697-2706
  作者：TING, PAULINE C.、KAMINSKI, JAMES J.、SHERLOCK, MARGARET H.、TOM, WING C.、LE+

  DOI：——

  日期：——
• HETEROBICYCLIC COMPOUNDS HAVING ANTIINFLAMMATORY ACTIVITY
  申请人：SCHERING CORPORATION

  公开号：EP0419561A1

  公开（公告）日：1991-04-03
• US5182289A
  申请人：——

  公开号：US5182289A

  公开（公告）日：1993-01-26
• [EN] HETEROBICYCLIC COMPOUNDS HAVING ANTIINFLAMMATORY ACTIVITY
  申请人：SCHERING CORPORATION

  公开号：WO1989012637A1

  公开（公告）日：1989-12-28

  (EN) Heterobicyclic and heterocyclic intermediate compounds and their use in treating inflammation, hyperproliferative skin conditions such as psoriasis and allergy are disclosed.(FR) L'invention concerne des composés intermédiaires hétérobicycliques hétérocycliques ainsi que leur utilisation dans le traitement anti-inflammatoire d'états cutanés hyperprolifératifs tels que le psoriasis et l'allergie.
• Substituted 1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-ones as potential antiinflammatory agents
  作者：Pauline C. Ting、James J. Kaminski、Margaret H. Sherlock、Wing C. Tom、Joe F. Lee、Robert W. Bryant、Arthur S. Watnick、Andrew T. McPhail

  DOI：10.1021/jm00172a004

  日期：1990.10

  A series of analogues based on the 1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one ring system have been synthesized and shown to possess oral antiinflammatory activity in both the reverse passive Arthus reaction (RPAR) pleural cavity assay in rats and in the adjuvant-induced arthritic rat model (AAR). Several members of this series additionally exhibit an inhibitory effect on the in vivo production of prostaglandin- and leukotriene-derived products or arachidonic acid metabolism although these compounds exhibit no significant inhibitory activity against the cyclooxygenase and 5-lipoxygenase enzymes in vitro. Structure-activity relationships in this series are discussed.