N-butyl-2-oxo-1,3-dihydroindole-5-sulfonamide | 1094032-52-6

• 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-butyl-2-oxo-1,3-dihydroindole-5-sulfonamide
• CAS: 1094032-52-6
• 化学式: C₁₂H₁₆N₂O₃S
• 分子量: 268.337
• InChiKey: WNWZLQJNWJVTPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  (1H-苯并[D]咪唑-2-基)(苯基)甲酮 、 N-butyl-2-oxo-1,3-dihydroindole-5-sulfonamide 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  The design, synthesis, and biological evaluation of potent receptor tyrosine kinase inhibitors

  摘要：

  Variously substituted indolin-2-ones were synthesized and evaluated for activity against KDR, Flt-1, FGFR-1 and PDGFR. Extension at the 5-position of the oxindole ring with ethyl piperidine (compound 7i) proved to be the most beneficial for attaining both biochemical and cellular potencies. Further optimization of 7i to balance biochemical and cellular potencies with favorable ADME/ PK properties led to the identification of 8h, a compound with a clean CYP profile, acceptable pharmacokinetic and toxicity profiles, and robust efficacy in multiple xenograft tumor models. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.029
• 作为产物：
  描述：

  2-吲哚酮 在 吡啶 、 氯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 N-butyl-2-oxo-1,3-dihydroindole-5-sulfonamide
  参考文献：
  名称：

  作为布鲁顿氏酪氨酸激酶抑制剂的羟吲哚磺酰胺衍生物的合成和生物学评价**

  摘要：

  以二氢-2 H -吡喃-4(3 H )-亚基)-2-氧代吲哚啉-5-磺酰胺为原料，通过Knoevenagel缩合反应合成了一系列3-(二氢-2 H -吡喃-4(3 H )-亚基)-2-氧代吲哚啉-5-磺酰胺衍生物。在吡咯烷和相应的磺酰胺存在下。新型羟吲哚磺酰胺PID-4选择性抑制 BTK 高 RAMOS 细胞增殖以及 BTK 和下游信号级联的磷酸化。

  DOI：

  10.1002/cmdc.202300511

文献信息

• The design, synthesis, and biological evaluation of potent receptor tyrosine kinase inhibitors
  作者：Moon H. Kim、Amy Lew Tsuhako、Erick W. Co、Dana T. Aftab、Frauke Bentzien、Jason Chen、Wei Cheng、Stefan Engst、Levina Goon、Rhett R. Klein、Donna T. Le、Morrison Mac、Jason J. Parks、Fawn Qian、Monica Rodriquez、Thomas J. Stout、Jeffrey H. Till、Kwang-Ai Won、Xiang Wu、F. Michael Yakes、Peiwen Yu、Wentao Zhang、Yeping Zhao、Peter Lamb、John M. Nuss、Wei Xu

  DOI：10.1016/j.bmcl.2012.06.029

  日期：2012.8

  Variously substituted indolin-2-ones were synthesized and evaluated for activity against KDR, Flt-1, FGFR-1 and PDGFR. Extension at the 5-position of the oxindole ring with ethyl piperidine (compound 7i) proved to be the most beneficial for attaining both biochemical and cellular potencies. Further optimization of 7i to balance biochemical and cellular potencies with favorable ADME/ PK properties led to the identification of 8h, a compound with a clean CYP profile, acceptable pharmacokinetic and toxicity profiles, and robust efficacy in multiple xenograft tumor models. (c) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Evaluation of Oxindole Sulfonamide Derivatives as Bruton's Tyrosine Kinase Inhibitors**
  作者：Chandra Prakash Koraboina、Venkatanarayana Chowdary Maddipati、Narendran Annadurai、Soňa Gurská、Petr Džubák、Marián Hajdúch、Viswanath Das、Rambabu Gundla

  DOI：10.1002/cmdc.202300511

  日期：2024.1.2

  A series of 3-(dihydro-2H-pyran-4(3H)-ylidene)-2-oxoindoline-5-sulfonamide derivatives were synthesized by Knoevenagel condensation of dihydro-2H-pyran-4(3H)-one in the presence of pyrrolidine with corresponding sulfonamides. The new oxindole sulfonamide PID-4 selectively inhibited BTK-high RAMOS cell proliferation and phosphorylation of BTK and downstream signalling cascades.

  以二氢-2 H -吡喃-4(3 H )-亚基)-2-氧代吲哚啉-5-磺酰胺为原料，通过Knoevenagel缩合反应合成了一系列3-(二氢-2 H -吡喃-4(3 H )-亚基)-2-氧代吲哚啉-5-磺酰胺衍生物。在吡咯烷和相应的磺酰胺存在下。新型羟吲哚磺酰胺PID-4选择性抑制 BTK 高 RAMOS 细胞增殖以及 BTK 和下游信号级联的磷酸化。