5-氨基-3-(4-甲氧基苯基)-茚并[1,2-c]吡唑-4(2H)-酮 | 247149-96-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氨基-3-(4-甲氧基苯基)-茚并[1,2-c]吡唑-4(2H)-酮
• 英文名称: 5-amino-3-(4-methoxyphenyl)-Indeno[1,2-c]pyrazol-4(2H)-one
• 英文别名: 5-amino-3-(4-methoxyphenyl)-1H-indeno[1,2-c]pyrazol-4-one
• CAS: 247149-96-8
• 化学式: C₁₇H₁₃N₃O₂
• 分子量: 291.309
• InChiKey: SUFUSGGYTYHTNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  81
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-氨基-3-(4-甲氧基苯基)-茚并[1,2-c]吡唑-4(2H)-酮 在 ammonium hydroxide 、 碳酸氢钠 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 5.0h， 生成 3-(4-methoxyphenyl)-5-(aminoacetamido)indeno[1,2-c]pyrazol-4-one
  参考文献：
  名称：

  Synthesis and Evaluation of Indenopyrazoles as Cyclin-Dependent Kinase Inhibitors. 2. Probing the Indeno Ring Substituent Pattern

  摘要：

  We disclose a novel series of indenopyrazole-based cyclin-dependent kinase (CDK) inhibitors. Kinetic experiments confirmed our initial molecular modeling studies that the compounds are competitive with respect to adenosine 5'-triphosphate (ATP) and bind in the kinase ATP pocket. A unique combination of active pharmacophores led us to a series of semicarbazide-based. inhibitors that are highly potent against CDK2 and CDK4 while maintaining selectivity against other relevant serine/threonine kinases. These compounds were active against a transformed human colon cancer cell line (HCT116) while maintaining an acceptable margin of activity against a normal fibroblast cell line. The compounds were found to be highly protein bound in our cell-based assay with the exception of 11k, which maintained a reasonable level of activity in the presence of human plasma proteins.

  DOI：

  10.1021/jm020171+
• 作为产物：
  描述：

  3-氨基-邻苯二甲酸二甲酯 在 吡啶 、 盐酸 、 sodium hydride 、 对甲苯磺酸 、 肼 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-氨基-3-(4-甲氧基苯基)-茚并[1,2-c]吡唑-4(2H)-酮
  参考文献：
  名称：

  Indenopyrazoles as Novel Cyclin Dependent Kinase (CDK) Inhibitors

  摘要：

  DOI：

  10.1021/jm0100032

文献信息

• Parallel synthesis of acylsemicarbazide libraries: preparation of potent cyclin dependent kinase (cdk) inhibitors
  作者：David A. Nugiel、Anup Vidwans、Carolyn D. Dzierba

  DOI：10.1016/j.bmcl.2004.09.023

  日期：2004.11

  Potent cyclin dependent kinase inhibitors were prepared using parallel synthesis methodology. Treating advanced intermediate 2 with a variety of hydrazides in DMSO at 80degreesC for 30 min gave the desired acylsemicarbazides in good to excellent yield. Several compounds were active against cdk4/D1 and cdk2/E in the low nanomolar range. The SAR indicates a wide variety of substituents are tolerated at the acylsemicarbazide moiety. (C) 2004 Elsevier Ltd. All rights reserved.
• US7250435B2
  申请人：——

  公开号：US7250435B2

  公开（公告）日：2007-07-31