1-[1-(4-Ethoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]ethan-1-one | 647841-58-5

• 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-[1-(4-Ethoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]ethan-1-one
• 英文别名: 1-[1-(4-ethoxyphenyl)-2,5-dimethylpyrrol-3-yl]ethanone
• CAS: 647841-58-5
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: URMZMETZLUFCJW-UHFFFAOYSA-N

物化性质

• 沸点：
  398.7±42.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[1-(4-Ethoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]ethan-1-one 在 四氯化锡 、 肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 6-(4-Ethoxy-phenyl)-1-(4-methoxy-phenyl)-4,5,7-trimethyl-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 作用下， 以 甲苯 为溶剂， 生成 1-[1-(4-Ethoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]ethan-1-one
  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

• Treatment of neuropathic pain with 6h-pyrrolo[3,4-d]pyridazine compounds
  申请人：Anker Burke Naomi

  公开号：US20060154929A1

  公开（公告）日：2006-07-13

  6H-pyrrolo[3,4-d]pyridazine compounds and methods of their use of as ligands of voltage gated calcium channels (VGCC), useful in the treatment of neuropathic pain, and psychiatric and mood disorders such as, for example, schizophrenia, anxiety, depression, panic, and bipolar disorder, as well as in the treatment of pain, Parkinson's disease, cognitive dysfunction, epilepsy, circadian rhythm disorders, drug addiction, drug abuse, drug withdrawal and other.

  6H-吡咯并[3,4-d]吡嗪化合物及其作为电压门控钙通道（VGCC）配体的使用方法，可用于治疗神经病性疼痛、精神和情绪障碍，例如精神分裂症、焦虑、抑郁、惊恐和双相情感障碍，以及治疗疼痛、帕金森病、认知功能障碍、癫痫、昼夜节律紊乱、药物成瘾、药物滥用、戒断症状等。
• Treatment of neuropathic pain with 6H-pyrrolo[3,4-d]pyridazine compounds
  申请人：Merck & Co. Inc.

  公开号：US07465730B2

  公开（公告）日：2008-12-16

  6H-pyrrolo[3,4-d]pyridazine compounds and methods of their use of as ligands of voltage gated calcium channels (VGCC), useful in the treatment of neuropathic pain, and psychiatric and mood disorders such as, for example, schizophrenia, anxiety, depression, panic, and bipolar disorder, as well as in the treatment of pain, Parkinson's disease, cognitive dysfunction, epilepsy, circadian rhythm disorders, drug addiction, drug abuse, drug withdrawal and other.

  6H-吡咯并[3,4-d]吡嗪化合物及其作为电压门控钙通道（VGCC）配体的应用方法，可用于治疗神经病理性疼痛和精神和情绪障碍，例如精神分裂症、焦虑、抑郁、恐慌和躁症，以及治疗疼痛、帕金森氏病、认知功能障碍、癫痫、昼夜节律紊乱、药物成瘾、药物滥用、药物戒断等。
• TREATMENT OF NEUROPATHIC PAIN WITH 6H-PYRROLO(3,4-D)PYRIDAZINE COMPOUNDS
  申请人：Merck & Co., Inc.

  公开号：EP1539168A2

  公开（公告）日：2005-06-15
• US7465730B2
  申请人：——

  公开号：US7465730B2

  公开（公告）日：2008-12-16
• [EN] TREATMENT OF NEUROPATHIC PAIN WITH 6H-PYRROLO[3,4-D]PYRIDAZINE COMPOUNDS<br/>[FR] TRAITEMENT DE LA DOULEUR NEUROPATHIQUE AU MOYEN DE COMPOSES 6H-PYRROLO[3,4-D]PYRIDAZINE
  申请人：MERCK & CO INC

  公开号：WO2004006836A2

  公开（公告）日：2004-01-22

  6H-pyrrolo[3,4-d]pyridazine compounds and methods of their use of as ligands of voltage gated calcium channels (VGCC), useful in the treatment of neuropathic pain, and psychiatric and mood disorders such as, for example, schizophrenia, anxiety, depression, panic, and bipolar disorder, as well as in the treatment of pain, Parkinson s disease, cognitive dysfunction, epilepsy, circadian rhythm disorders, drug addiction, drug abuse, drug withdrawal and other