1-(4-Ethoxy-phenyl)-2,5-dimethyl-1H-pyrrole-3,4-dicarbaldehyde | 327060-58-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(4-Ethoxy-phenyl)-2,5-dimethyl-1H-pyrrole-3,4-dicarbaldehyde
• 英文别名: 1-(4-ethoxyphenyl)-2,5-dimethyl-1H-pyrrole-3,4-dicarbaldehyde；1-(4-ethoxyphenyl)-2,5-dimethylpyrrole-3,4-dicarbaldehyde
• CAS: 327060-58-2
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: UPGOQMSAFPSWDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-Ethoxy-phenyl)-2,5-dimethyl-1H-pyrrole-3,4-dicarbaldehyde 在 肼 作用下， 以 乙醇 为溶剂， 以99%的产率得到6-(4-Ethoxy-phenyl)-5,7-dimethyl-6H-pyrrolo[3,4-d]pyridazine
  参考文献：
  名称：

  Synthesis and biological evaluation of 6-aryl-6 H -pyrrolo[3,4- d ]pyridazine derivatives: high-affinity ligands to the α 2 δ subunit of voltage gated calcium channels

  摘要：

  A novel class of 6-aryl-6H-pyrrolo[3,4-d]pyridazine ligands for the alpha(2)delta subunit of voltage-gated calcium channels has been described. Substitutions in the aryl ring of the molecule were generally not tolerated, and resulted in diminished binding to the alpha(2)delta subunit. Modifications to the pyridazine ring revealed numerous permissive substitutions, and detailed SAR studies were carried out in this portion of the molecule. Replacement of the pyridazine ring methyl group with an aminomethyl functionality provided greatly improved potency over the initial lead. The initial lead compound displayed good rat pharmacokinetic properties, and was shown to be efficacious in the Chung model for neuropathic pain in rats. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.036
• 作为产物：
  描述：

  对乙氧基苯胺 在 溶剂黄146 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 生成 1-(4-Ethoxy-phenyl)-2,5-dimethyl-1H-pyrrole-3,4-dicarbaldehyde
  参考文献：
  名称：

  Synthesis and biological evaluation of 6-aryl-6 H -pyrrolo[3,4- d ]pyridazine derivatives: high-affinity ligands to the α 2 δ subunit of voltage gated calcium channels

  摘要：

  A novel class of 6-aryl-6H-pyrrolo[3,4-d]pyridazine ligands for the alpha(2)delta subunit of voltage-gated calcium channels has been described. Substitutions in the aryl ring of the molecule were generally not tolerated, and resulted in diminished binding to the alpha(2)delta subunit. Modifications to the pyridazine ring revealed numerous permissive substitutions, and detailed SAR studies were carried out in this portion of the molecule. Replacement of the pyridazine ring methyl group with an aminomethyl functionality provided greatly improved potency over the initial lead. The initial lead compound displayed good rat pharmacokinetic properties, and was shown to be efficacious in the Chung model for neuropathic pain in rats. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.036

文献信息

• Synthesis and biological evaluation of 6-aryl-6 H -pyrrolo[3,4- d ]pyridazine derivatives: high-affinity ligands to the α 2 δ subunit of voltage gated calcium channels
  作者：Brian A. Stearns、Naomi Anker、Jeannie M. Arruda、Brian T. Campbell、Chixu Chen、Merryl Cramer、Tao Hu、Xiaohui Jiang、Kenneth Park、Kun Kun Ren、Marciano Sablad、Angelina Santini、Herve Schaffhauser、Mark O. Urban、Benito Munoz

  DOI：10.1016/j.bmcl.2003.12.036

  日期：2004.3

  A novel class of 6-aryl-6H-pyrrolo[3,4-d]pyridazine ligands for the alpha(2)delta subunit of voltage-gated calcium channels has been described. Substitutions in the aryl ring of the molecule were generally not tolerated, and resulted in diminished binding to the alpha(2)delta subunit. Modifications to the pyridazine ring revealed numerous permissive substitutions, and detailed SAR studies were carried out in this portion of the molecule. Replacement of the pyridazine ring methyl group with an aminomethyl functionality provided greatly improved potency over the initial lead. The initial lead compound displayed good rat pharmacokinetic properties, and was shown to be efficacious in the Chung model for neuropathic pain in rats. (C) 2004 Elsevier Ltd. All rights reserved.