N-ethyl-2-oxoindoline-5-sulfonamide | 502157-27-9

• 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: N-ethyl-2-oxoindoline-5-sulfonamide
• 英文别名: 2-Oxo-2,3-dihydro-1H-indole-5-sulfonic acid ethylamide；N-ethyl-2-oxo-1,3-dihydroindole-5-sulfonamide
• CAS: 502157-27-9
• 化学式: C₁₀H₁₂N₂O₃S
• mdl: MFCD11618425
• 分子量: 240.283
• InChiKey: URMIINSQFONKFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-甲氧基-1-甲基吲哚-3-甲醛 、 N-ethyl-2-oxoindoline-5-sulfonamide 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 N-ethyl-3-((5-methoxy-1-methyl-1H-indol-3-yl)methylene)-2-oxoindoline-5-sulfonamide
  参考文献：
  名称：

  Potent small molecule inhibitors of spleen tyrosine kinase (Syk)

  摘要：

  A series of oxindoles demonstrating inhibition of the pbosphorylation of biotinylated substrates of Syk and IgE/FcepsilonRI triggered basophil cell degranulation has been identified. A study of the SAR around sulfonamide 31 (IC50=5 nM, EC50= 1400 nM) is discussed. The modest cellular activity representative of the sulfonamide series was overcome when the Polar surface Area was lowered to < 110 Angstrom(2), leading to the identification of amide 32 (IC50= 145 nM, EC50= 100 nM). (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/s0960-894x(03)00658-9
• 作为产物：
  描述：

  2-吲哚酮 在 氯磺酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 N-ethyl-2-oxoindoline-5-sulfonamide
  参考文献：
  名称：

  Potent small molecule inhibitors of spleen tyrosine kinase (Syk)

  摘要：

  A series of oxindoles demonstrating inhibition of the pbosphorylation of biotinylated substrates of Syk and IgE/FcepsilonRI triggered basophil cell degranulation has been identified. A study of the SAR around sulfonamide 31 (IC50=5 nM, EC50= 1400 nM) is discussed. The modest cellular activity representative of the sulfonamide series was overcome when the Polar surface Area was lowered to < 110 Angstrom(2), leading to the identification of amide 32 (IC50= 145 nM, EC50= 100 nM). (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/s0960-894x(03)00658-9

文献信息

• 3- (AMINOMETHYLIDEN) 2-INDOLINONE DERIVATIVES AND THEIR USE AS CELL PROLIFERATION INHIBITORS
  申请人：Boehringer Ingelheim International GmbH

  公开号：EP2016049A1

  公开（公告）日：2009-01-21
• [EN] 3- (AMINOMETHYLIDEN) 2-INDOLINONE DERIVATIVES AND THEIR USE AS CELL PROLIFERATION INHIBITORS<br/>[FR] DÉRIVÉS DE 3- (AMINOMÉTHYLIDÈNE) 2-INDOLINONE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE LA PROLIFÉRATION CELLULAIRE
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2007122219A1

  公开（公告）日：2007-11-01

  [EN] The present invention encompasses compounds of general formula (1) wherein R¹, R², R³ and X are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, and the use thereof for preparing a pharmaceutical composition having the above-mentioned properties.
  [FR] La présente invention comprend des composés de formule générale (1), dans laquelle R¹, R², R³ et X sont tels que définis dans la revendication 1, qui sont appropriés pour le traitement des maladies caractérisées par une prolifération cellulaire excessive ou anormale, et leur utilisation pour préparer une composition pharmaceutique présentant les propriétés mentionnées ci-dessus.
• 10.1007/s00044-024-03259-3
  作者：Sulaibi, Mazen Al、Zahra, Jalal、Bardaweel, Sanaa、El Abadleh, Mustafa、Taha, Mutasem O.

  DOI：10.1007/s00044-024-03259-3

  日期：——
• Potent small molecule inhibitors of spleen tyrosine kinase (Syk)
  作者：Justine Y.Q Lai、Paul J Cox、Rajesh Patel、Shazia Sadiq、David J Aldous、Sukanthini Thurairatnam、Keith Smith、Darren Wheeler、Savita Jagpal、Sofia Parveen、Gary Fenton、Trevor K.P Harrison、Clive McCarthy、Paul Bamborough

  DOI：10.1016/s0960-894x(03)00658-9

  日期：2003.9

  A series of oxindoles demonstrating inhibition of the pbosphorylation of biotinylated substrates of Syk and IgE/FcepsilonRI triggered basophil cell degranulation has been identified. A study of the SAR around sulfonamide 31 (IC50=5 nM, EC50= 1400 nM) is discussed. The modest cellular activity representative of the sulfonamide series was overcome when the Polar surface Area was lowered to < 110 Angstrom(2), leading to the identification of amide 32 (IC50= 145 nM, EC50= 100 nM). (C) 2003 Published by Elsevier Ltd.