3-chloro-6-(4'-acetamidophenyl)pyridazine | 919496-26-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-chloro-6-(4'-acetamidophenyl)pyridazine
• 英文别名: 3-Chloro-6-(4-acetylaminophenyl)pyridazine；N-[4-(6-chloropyridazin-3-yl)phenyl]acetamide
• CAS: 919496-26-7
• 化学式: C₁₂H₁₀ClN₃O
• 分子量: 247.684
• InChiKey: JERBSEHVLVMMMF-UHFFFAOYSA-N

物化性质

• 沸点：
  534.8±40.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chloro-6-(4'-acetamidophenyl)pyridazine 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以12 mg的产率得到3-(4'-acetamidophenyl)pyridazine
  参考文献：
  名称：

  Synthesis and methemoglobinemia-inducing properties of benzocaine isosteres designed as humane rodenticides

  摘要：

  A number of isosteres (oxadiazoles, thiadiazoles, tetrazoles and diazines) of benzocaine were prepared and evaluated for their capacity to induce methemoglobinemia-with a view to their possible application as humane pest control agents. It was found that an optimal lipophilicity for the formation of methemoglobin (metHb) in vitro existed within each series, with 1,2,4-oxadiazole 3 (metHb% = 61.0 +/- 3.6) and 1,3,4-oxadiazole 10 (metHb% = 52.4 +/- 0.9) demonstrating the greatest activity. Of the 5 candidates (compounds 3, 10, 11, 13 and 23) evaluated in vivo, failure to induce a lethal end-point at doses of 120 mg/kg was observed in all cases. Inadequate metabolic stability, particularly towards hepatic enzymes such as the CYPs, was postulated as one reason for their failure. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.013
• 作为产物：
  描述：

  3,6-二氯哒嗪 、 4-乙酰基氨基苯硼酸频哪醇酯 在 碳酸氢钠 、 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 1.25h， 以25%的产率得到3-chloro-6-(4'-acetamidophenyl)pyridazine
  参考文献：
  名称：

  Synthesis and methemoglobinemia-inducing properties of benzocaine isosteres designed as humane rodenticides

  摘要：

  A number of isosteres (oxadiazoles, thiadiazoles, tetrazoles and diazines) of benzocaine were prepared and evaluated for their capacity to induce methemoglobinemia-with a view to their possible application as humane pest control agents. It was found that an optimal lipophilicity for the formation of methemoglobin (metHb) in vitro existed within each series, with 1,2,4-oxadiazole 3 (metHb% = 61.0 +/- 3.6) and 1,3,4-oxadiazole 10 (metHb% = 52.4 +/- 0.9) demonstrating the greatest activity. Of the 5 candidates (compounds 3, 10, 11, 13 and 23) evaluated in vivo, failure to induce a lethal end-point at doses of 120 mg/kg was observed in all cases. Inadequate metabolic stability, particularly towards hepatic enzymes such as the CYPs, was postulated as one reason for their failure. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.013

文献信息

• Novel Medicaments
  申请人：Hohlweg Rolf

  公开号：US20090312309A1

  公开（公告）日：2009-12-17

  Novel compounds which interact with the histamine H3 receptor are defined. These compounds are particularly useful in the treatment of a variety of diseases or conditions in which histamine H3 interactions are beneficial. Thus, the compounds may find use, e.g., in the treatment of diseases of the central nervous system, the peripheral nervous system, the cardiovascular system, the pulmonary system, the gastrointestinal system and the endocrinological system. The novel compounds have a core consisting of a 6 membered aromatic ring containing at least one nitrogen atom and two carbon atoms in the ring and, at the remaining positions in the ring, there is either a carbon or a nitrogen atom.

  定义了与组胺H3受体相互作用的新化合物。这些化合物在治疗多种疾病或病况中特别有用，其中组胺H3相互作用是有益的。因此，这些化合物可能用于治疗中枢神经系统、外周神经系统、心血管系统、肺系统、胃肠系统和内分泌系统的疾病，例如。新的化合物具有一个核心，其中包含至少一个氮原子和两个碳原子的6元芳香环，并且在环中的其余位置上，有一个碳原子或一个氮原子。
• Medicaments
  申请人：Hohlweg Rolf

  公开号：US08501739B2

  公开（公告）日：2013-08-06

  Novel compounds which interact with the histamine H3 receptor are defined. These compounds are particularly useful in the treatment of a variety of diseases or conditions in which histamine H3 interactions are beneficial. Thus, the compounds may find use, e.g., in the treatment of diseases of the central nervous system, the peripheral nervous system, the cardiovascular system, the pulmonary system, the gastrointestinal system and the endocrinological system. The novel compounds have a core consisting of a 6 membered aromatic ring containing at least one nitrogen atom and two carbon atoms in the ring and, at the remaining positions in the ring, there is either a carbon or a nitrogen atom.

  定义了与组胺H3受体相互作用的新化合物。这些化合物在治疗多种疾病或状况中特别有用，其中组胺H3相互作用是有益的。因此，这些化合物可以在治疗中枢神经系统、外周神经系统、心血管系统、肺系统、胃肠系统和内分泌系统的疾病中发挥作用。这些新化合物具有一个核心，其中包含至少一个氮原子和两个碳原子的6元芳香环，并且在环中的其余位置上，要么是碳原子，要么是氮原子。
• Histamine H3 receptor antagonists
  申请人：High Point Pharmaceuticals, LLC

  公开号：EP2233470A1

  公开（公告）日：2010-09-29

  Novel compounds of formula I-9: which interact with the histamine H3 receptor are defined. These compounds are particularly useful in the treatment of a variety of diseases or conditions in which histamine H3 interactions are beneficial. Thus, the compounds may find use, e.g., in the treatment of diseases of the central nervous system, the peripheral nervous system, the cardiovascular system, the pulmonary system, the gastrointestinal system and the endocrinological system. The novel compounds have a core consisting of a 6 membered aromatic ring containing at least one nitrogen atom and two carbon atoms in the ring and, at the remaining positions in the ring, there is either a carbon or a nitrogen atom.

  式 I-9 的新型化合物： 定义了与组胺 H3 受体相互作用的新型化合物。这些化合物特别适用于治疗组胺 H3 相互作用有益的各种疾病或病症。因此，这些化合物可用于治疗中枢神经系统、周围神经系统、心血管系统、肺部系统、胃肠道系统和内分泌系统等疾病。这些新型化合物的核心是一个 6 个成员的芳香环，环中至少含有一个氮原子和两个碳原子，在环的其余位置，要么有一个碳原子，要么有一个氮原子。
• Compounds active at the histamine H3 receptor
  申请人：High Point Pharmaceuticals, LLC

  公开号：EP2386554A1

  公开（公告）日：2011-11-16

  Novel compounds which interact with the histamine H3 receptor are defined. These compounds are particularly useful in the treatment of a variety of diseases or conditions in which histamine H3 interactions are beneficial. Thus, the compounds may find use, e.g., in the treatment of diseases of the central nervous system, the peripheral nervous system, the cardiovascular system, the pulmonary system, the gastrointestinal system and the endocrinological system. The novel compounds have a core consisting of a 6 membered aromatic ring containing at least one nitrogen atom and two carbon atoms in the ring and, at the remaining positions in the ring, there is either a carbon or a nitrogen atom.

  定义了与组胺 H3 受体相互作用的新型化合物。这些化合物特别适用于治疗组胺 H3 相互作用有益的各种疾病或病症。因此，这些化合物可用于治疗中枢神经系统、周围神经系统、心血管系统、肺部系统、胃肠道系统和内分泌系统等疾病。这些新型化合物的核心是一个 6 个成员的芳香环，环中至少含有一个氮原子和两个碳原子，在环的其余位置，要么有一个碳原子，要么有一个氮原子。
• HISTAMINE H3 RECEPTOR ANTAGONISTS
  申请人：NOVO NORDISK A/S

  公开号：EP1902028A2

  公开（公告）日：2008-03-26