1,1'-[1-(4-甲氧苯基)-2,5-二甲基-1H-吡咯-3,4-二基]二乙酮 | 112086-82-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 1,1'-[1-(4-甲氧苯基)-2,5-二甲基-1H-吡咯-3,4-二基]二乙酮
• 英文名称: Ethanone, 1-(4-acetyl-1-(4-methoxyphenyl)-2,5-dimethylpyrrol-3-yl)-
• 英文别名: 1-[4-acetyl-1-(4-methoxyphenyl)-2,5-dimethylpyrrol-3-yl]ethanone
• CAS: 112086-82-5
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: SDKYZOSOKCWHDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  1,1'-[1-(4-甲氧苯基)-2,5-二甲基-1H-吡咯-3,4-二基]二乙酮 在 肼 作用下， 以 乙醇 为溶剂， 生成 6-(4-methoxyphenyl)-1,4,5,7-tetramethyl-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：

  3,4-二乙酰基-2,5-己二酮 、 甲氧苯胺 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 生成 1,1'-[1-(4-甲氧苯基)-2,5-二甲基-1H-吡咯-3,4-二基]二乙酮
  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

• 3,4-Diacetylhexane-2,5-dione—an effective synthon for synthesis of substituted azulene heteroanalogs by cyclocondensation reactions
  作者：E. P. Olekhnovich、S. L. Boroshko、Yu. N. Tkachenko、A. F. Pozharskii、E. B. Tsupak、Yu. A. Zhadanov、L. P. Olekhnovich

  DOI：10.1007/bf02495609

  日期：1998.8

  developed. The method is based on the cyclocondensation of 3,4-diacetylhexane-2,5-diones with aromatic aldehydes and trialkyl orthoformates under the action of a 16% perchloric acid solution in acetic anhydride. Under similar conditions, with hydrogen sulfide, cyclohepta[c]thiophenium perchlorates have been obtained, while cyclohepta[c]pyrrolium perchlorates have been prepared with arylamines, ammonium

  已经开发了用于合成 4,8-二烷氧基-6-芳基-1,3-二甲基环庚 [c] 呋喃高氯酸盐的一锅法。该方法基于 3,4-二乙酰己烷-2,5-二酮与芳香醛和原甲酸三烷基酯在 16% 高氯酸乙酸酐溶液作用下的环缩合反应。在类似的条件下，用硫化氢制备了环庚[c]噻吩高氯酸盐，而环庚[c]吡咯高氯酸盐用芳胺、乙酸铵或脂肪胺乙酸盐制备。首次获得了 azulene 的杂类似物 4,8-diethoxy-1,3-二甲基-2-azaazulene。氮杂-和噻唑鎓盐的水解产生相应的环庚[c]吡咯-4-酮和环庚[c]噻吩-4-酮。
• US7465730B2
  申请人：——

  公开号：US7465730B2

  公开（公告）日：2008-12-16
• 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.