3-iodo-7-methoxy-1,4-dihydroindeno[1, 2-c]pyrazole-6-carboxylic acid | 760991-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-iodo-7-methoxy-1,4-dihydroindeno[1, 2-c]pyrazole-6-carboxylic acid
• 英文别名: 3-Iodo-7-methoxy-2,4-dihydroindeno[1,2-c]pyrazole-6-carboxylic acid
• CAS: 760991-06-8
• 化学式: C₁₂H₉IN₂O₃
• 分子量: 356.12
• InChiKey: OOIZIBHFHIAQAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  75.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-iodo-7-methoxy-1,4-dihydroindeno[1, 2-c]pyrazole-6-carboxylic acid 在 bis-triphenylphosphine-palladium(II) chloride benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 sodium carbonate 、 N,N-二异丙基乙胺 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 4'-{7-methoxy-6-[(4-methylpiperazin-1-yl)carbonyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1'-biphenyl-4-ol
  参考文献：
  名称：

  1,4-Dihydroindeno[1,2-c]pyrazoles as potent checkpoint kinase 1 inhibitors: Extended exploration on phenyl ring substitutions and preliminary ADME/PK studies

  摘要：

  A study on substitutions at the four open positions on the phenyl ring of the 1,4-dihydroindeno[1,2-c]pyrazoles as potent CHK-1 inhibitors is described. Bis-substitution at both the 6- and 7-positions led to inhibitors with IC50 values below 0.3 nM. The compound with the best overall activities (36) was able to potentiate the anti-proliferative effect of doxorubicin in HeLa cells by at least 47-fold. Physicochemical, metabolic, and pharmacokinetic properties of selected inhibitors are also disclosed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.055
• 作为产物：
  描述：

  6-甲氧基-1-茚酮 在 sodium chlorite 、 potassium dihydrogenphosphate 、 N-碘代丁二酰亚胺 、 氨基磺酸 、 溴 、 仲丁基锂 、 sodium hydride 、 溶剂黄146 、 苯基锂 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 3-iodo-7-methoxy-1,4-dihydroindeno[1, 2-c]pyrazole-6-carboxylic acid
  参考文献：
  名称：

  1,4-Dihydroindeno[1,2-c]pyrazoles as potent checkpoint kinase 1 inhibitors: Extended exploration on phenyl ring substitutions and preliminary ADME/PK studies

  摘要：

  A study on substitutions at the four open positions on the phenyl ring of the 1,4-dihydroindeno[1,2-c]pyrazoles as potent CHK-1 inhibitors is described. Bis-substitution at both the 6- and 7-positions led to inhibitors with IC50 values below 0.3 nM. The compound with the best overall activities (36) was able to potentiate the anti-proliferative effect of doxorubicin in HeLa cells by at least 47-fold. Physicochemical, metabolic, and pharmacokinetic properties of selected inhibitors are also disclosed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.055

文献信息

• Fused tri and tetra-cyclic pyrazole kinase inhibitors
  申请人：——

  公开号：US20040259904A1

  公开（公告）日：2004-12-23

  Compounds having the formula (I) 1 are useful for inhibiting protein kinases. Also disclosed are methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.

  化合物具有公式（I）1，对于抑制蛋白激酶具有用途。还公开了制备该化合物的方法，含有该化合物的组合物以及使用该化合物的治疗方法。
• US7320986B2
  申请人：——

  公开号：US7320986B2

  公开（公告）日：2008-01-22