2-[1-(4-methylbenzyl)-1H-indol-3-yl]-2-oxo-N-(pyridin-4-yl)acetamide | 245661-54-5

• 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-[1-(4-methylbenzyl)-1H-indol-3-yl]-2-oxo-N-(pyridin-4-yl)acetamide
• 英文别名: 2-[1-[(4-methylphenyl)methyl]indol-3-yl]-2-oxo-N-pyridin-4-ylacetamide
• CAS: 245661-54-5
• 化学式: C₂₃H₁₉N₃O₂
• 分子量: 369.423
• InChiKey: UXSMTPYCAXDMKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  64
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(1H-indol-3-yl)-2-oxo-N-(pyridin-4-yl)acetamide 、 4-甲基氯苄 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.25h， 以64%的产率得到2-[1-(4-methylbenzyl)-1H-indol-3-yl]-2-oxo-N-(pyridin-4-yl)acetamide
  参考文献：
  名称：

  Synthesis and structure–activity relationships of N-aryl(indol-3-yl)glyoxamides as antitumor agents

  摘要：

  The synthesis and study of the structure-activity relationships of cytotoxic compounds based on N-pyridinyl or N-aryl-2-(1-benzylindol-3-yl)glyoxamide skeleton, represented by the lead structures D-24241 and D-24851, are described. The presence of N-(pyridin-4-yl) moiety was crucial for activity and 2-[1(4-chloro-3-nitrobenzyl)-1H-indol-3-yl]-2-oxo-N-(pyridin-4-yl) acetamide (55), the most potent derivative, showed IC(50) = 39 nM, 51 nM and 11 nM against HeLa/KB (human cervix carcinoma), L1210 (murine leukemia) and SKOV3 (human ovarian carcinoma) cell lines proliferation assay, respectively, as active as the lead compounds. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.048

文献信息

• NANOPARTICULATE COMPOSITIONS OF TUBULIN INHIBITOR COMPOUNDS
  申请人：Ziopharm Oncology, Inc.

  公开号：US20140212495A1

  公开（公告）日：2014-07-31

  The present invention is directed to novel pharmaceutical compositions comprising nano- and micro-particulate formulations of poorly water soluble tubulin inhibitors of the indole chemical class, preferably N-substituted indol-3-glyoxyamides, and more preferably N-(Pyridin-4-yl)-[1-(4-chlorobenzyl)-indol-3-yl]glyoxylic acid amide (D-24851), also known as “Indibulin,” and methods of making and using such compositions for the treatment of anti-tumor agent resistant cancers and other diseases.