3-溴-1-甲基-1H-吲唑-4-胺 | 1092351-47-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 3-溴-1-甲基-1H-吲唑-4-胺
• 中文别名: 4-氨基-3-溴-1-甲基吲唑
• 英文名称: 3-bromo-1-methyl-1H-indazol-4-amine
• 英文别名: 3-bromo-1-methylindazol-4-amine
• CAS: 1092351-47-7
• 化学式: C₈H₈BrN₃
• 分子量: 226.076
• InChiKey: KICKKRNPIPGMTR-UHFFFAOYSA-N

物化性质

• 沸点：
  378.4±22.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-溴-1-甲基-1H-吲唑-4-胺 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium hydroxide 、 2-二-叔丁膦基-2',4',6'-三异丙基联苯 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.5h， 以80%的产率得到1-methyl-4-nitro-1H-indazol-5-ol
  参考文献：
  名称：

  Identification of pyrazolopyrimidine arylsulfonamides as CC-chemokine receptor 4 (CCR4) antagonists

  摘要：

  A novel 4-aminoindazole sulfonamide hit (13) was identified as a human CCR4 antagonists from testing a focussed library of compounds in the primary GTPcS assay. Replacing the indazole core with a pyrazolopyrimidine, and introduction of a methoxy group adjacent to the sulfonamide substituent, resulted in the identification of pyrazolopyrimidine 37a, which exhibited good binding affinity in the GTPcS assay (pIC(50) = 7.2), low lipophilicity (c logP = 2.2, chromlog D-7.4 = 2.4), high LE (0.41), high solubility (CLND solubility >= 581 mu M), and an excellent PK profile in both the rat (F = 62%) and the dog (F = 100%). Further SAR investigation of the pyrazolopyrimidine suggested that substitution at N1 is tolerated, providing a suitable vector to modulate the properties, and increase the potency in a lead optimisation campaign. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.07.052
• 作为产物：
  描述：

  5-溴吲唑 在 盐酸 、 硫酸 、 硝酸 、 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 19.17h， 生成 3-溴-1-甲基-1H-吲唑-4-胺
  参考文献：
  名称：

  Identification of pyrazolopyrimidine arylsulfonamides as CC-chemokine receptor 4 (CCR4) antagonists

  摘要：

  A novel 4-aminoindazole sulfonamide hit (13) was identified as a human CCR4 antagonists from testing a focussed library of compounds in the primary GTPcS assay. Replacing the indazole core with a pyrazolopyrimidine, and introduction of a methoxy group adjacent to the sulfonamide substituent, resulted in the identification of pyrazolopyrimidine 37a, which exhibited good binding affinity in the GTPcS assay (pIC(50) = 7.2), low lipophilicity (c logP = 2.2, chromlog D-7.4 = 2.4), high LE (0.41), high solubility (CLND solubility >= 581 mu M), and an excellent PK profile in both the rat (F = 62%) and the dog (F = 100%). Further SAR investigation of the pyrazolopyrimidine suggested that substitution at N1 is tolerated, providing a suitable vector to modulate the properties, and increase the potency in a lead optimisation campaign. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.07.052