2-[5-(4-Chlorophenyl)-1-methylpyrazol-4-yl]isoindole-1,3-dione | 216854-37-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-[5-(4-Chlorophenyl)-1-methylpyrazol-4-yl]isoindole-1,3-dione
• CAS: 216854-37-4
• 化学式: C₁₈H₁₂ClN₃O₂
• 分子量: 337.765
• InChiKey: GDMJNNJBBRJILP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 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：
  55.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[5-(4-Chlorophenyl)-1-methylpyrazol-4-yl]isoindole-1,3-dione 在 2-甲基苯磺酸 、 肼 、 三氯氧磷 作用下， 以 二苯醚 、 乙醇 、 苯 为溶剂， 反应 1.0h， 生成 [3-(4-Chloro-phenyl)-2,5-dimethyl-2H-pyrazolo[4,3-b]pyridin-7-yl]-dipropyl-amine
  参考文献：
  名称：

  Synthesis of 3-phenylpyrazolo[4,3-b]pyridines via a convenient synthesis of 4-amino-3-arylpyrazoles and SAR of corticotropin-Releasing factor receptor type-1 antagonists

  摘要：

  3-Phenylpyrazolo[4,3-b]pyridines were synthesized via a cyclization of 4-amino-3-phenylpyrazoles 11-13 with ethyl acetoacetate. These compounds were found to be potent CRF1 antagonists. The 2-alkylpyrazolo[4,3-b]pyridines were more polar but less active than the corresponding 1-alkyl-isomers. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00621-8
• 作为产物：
  描述：

  2,4'-二氯苯乙酮 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[5-(4-Chlorophenyl)-1-methylpyrazol-4-yl]isoindole-1,3-dione
  参考文献：
  名称：

  Synthesis of 3-phenylpyrazolo[4,3-b]pyridines via a convenient synthesis of 4-amino-3-arylpyrazoles and SAR of corticotropin-Releasing factor receptor type-1 antagonists

  摘要：

  3-Phenylpyrazolo[4,3-b]pyridines were synthesized via a cyclization of 4-amino-3-phenylpyrazoles 11-13 with ethyl acetoacetate. These compounds were found to be potent CRF1 antagonists. The 2-alkylpyrazolo[4,3-b]pyridines were more polar but less active than the corresponding 1-alkyl-isomers. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00621-8

文献信息

• Synthesis of 1-methyl-3-phenylpyrazolo[4,3-b]pyridines via a methylation of 4-phthalimino-3-phenylpyrazoles and optimization toward highly potent corticotropin-releasing factor type-1 antagonists
  作者：Charles Q. Huang、Keith Wilcoxen、James R. McCarthy、Mustaph Haddach、Dimitri Grigoriadis、Chen Chen

  DOI：10.1016/s0960-894x(03)00622-x

  日期：2003.10

  1-Methyl-3-phenylpyrazolo[4,3-b]pyridines were synthesized via a cyclization reaction of 1-methyl-4-amino-3-phenylpyrazoles 8 with ethyl acetoacetate. Optimization of this series of compounds resulted in CRF(1) antagonists with subnanomolar binding affinity. Compounds bearing a polar group such as methoxy or hydroxy were also found to be very active.

  通过1-甲基-4-氨基-3-苯基吡唑8与乙酰乙酸乙酯的环化反应合成了1-甲基-3-苯基吡唑并[4，3-b]吡啶。该系列化合物的优化产生具有亚纳摩尔结合亲和力的CRF（1）拮抗剂。还发现带有极性基团如甲氧基或羟基的化合物非常活泼。
• A convenient one-pot synthesis of 4-amino-3-arylpyrazoles from α-phthaloylaminoacetophenones
  作者：Chen Chen、Keith Wilcoxen、James R. McCarthy

  DOI：10.1016/s0040-4039(98)01776-6

  日期：1998.11

  Condensation of alpha-phthaloylaminoacetophenones 1a-c with N,N-dimethylformamide dimethyl acetal afforded the novel enamines 3a-c. Cyclization of 3 with hydrazine, alkylhydrazine or phenylhydrazine salts (4a-d) gave 4-phthaloylamino-3-arylpyrazoles 7-9 in high yields. Deprotection of 7-9 was accomplished with hydrazine to provide 4-amino-3-arylpyrazoles 5 in good yields. (C) 1998 Elsevier Science Ltd. All rights reserved.