5-(tri-n-butylstannyl)-3-phenyl pyridazine

• 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: 5-(tri-n-butylstannyl)-3-phenyl pyridazine
• 英文别名: [3-phenyl-5-(tri-n-butylstannyl)]pyridazine
• 化学式: C₂₂H₃₄N₂Sn
• 分子量: 445.235
• InChiKey: WJEHTCDQPMBCEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(tri-n-butylstannyl)-3-phenyl pyridazine 在 四(三苯基膦)钯 、 碘 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 3,5-二苯基哒嗪
  参考文献：
  名称：

  A New Pyridazine Series of GABA_A α5 Ligands

  摘要：

  Screening of the Merck compound collection identified 6 as an unusually simple, low molecular weight hit with moderate affinity for GABA(A) receptors. The structural novelty of 6, compared to our advanced series of GABA(A) alpha 5 inverse agonists, made it an attractive molecule for further exploration. This paper will describe the evolution of 6 into a new series of ligands with nanomolar affinity and functional selectivity for GABA(A) alpha 5 receptor subtypes.

  DOI：

  10.1021/jm050249x

文献信息

• Synthesis of 3,5-disubstituted pyridazines by regioselective [4+2] cycloadditions with ethynyltributyltin and subsequent replacement of the organotin substituent
  作者：Jürgen Sauer、Dieter K. Heldmann

  DOI：10.1016/s0040-4020(98)00127-6

  日期：1998.4

  Cycloadditions of 3-aryl-1,2,4,5-tetrazines 1a-o with ethynyltributyltin 5 occur with high regioselectivity to yield 3-aryl-5-tributylstannyl-pyridazines 9–23 in 71–95% yield. Moreover, the stannanes obtained could be utilized as starting materials for the preparation of various 3,5-di-substituted pyridazines as shown for 3-phenyl-5-tributylstannyl-pyridazine 9b. Stille cross-couplings with aryl halides

  的3-芳基-1,2,4,5-四嗪环加成1A-O与ethynyltributyltin 5具有高的区域选择性发生，得到3-芳基-5-三丁基甲锡哒嗪9-23在71-95％的产率。此外，所获得的锡烷可以用作制备各种3,5-二取代的哒嗪的原料，如3-苯基-5-三丁基锡烷基-哒嗪9b所示。Stille与芳基卤化物的交叉偶联生成3,5-二芳基-哒嗪26-29，而暴露于元素卤素则提供了3-苯基-5-卤代哒嗪24和25，它们可以用作进一步官能化的起始化合物，例如Heck反应。
• [EN] PYRIDAZINE DERIVATIVES AS LIGANDS FOR GABA RECEPTORS<br/>[FR] DERIVES DE PYRIDAZINE UTILISES EN TANT QUE LIGANDS POUR DES RECEPTEURS GABA
  申请人：MERCK SHARP & DOHME

  公开号：WO2004014891A1

  公开（公告）日：2004-02-19

  A class of pyridazine derivatives, substituted in the 4-position by an optionally substituted heteroaromatic ring, being selective ligands for GABAA receptors, in particular having high affinity for the α2 and/or α3 and/or α5 subunit thereof, are accordingly of benefit in the treatment and/or prevention of adverse conditions of the central nervous system, including anxiety, convulsions and cognitive disorders.

  一类吡啶嗪衍生物，在4-位被一个可选取代的杂环芳香环所取代，是选择性的GABAA受体配体，特别是对α2和/或α3和/或α5亚单位具有高亲和力，因此对于治疗和/或预防中枢神经系统的不良症状，包括焦虑、惊厥和认知障碍具有益处。
• Pyridazine derivatives as ligands for gaba receptors
  申请人：Fletcher Robert Stephen

  公开号：US20060148809A1

  公开（公告）日：2006-07-06

  A class of pyridazine derivatives, substituted in the 4-position by an optionally substituted heteroaromatic ring, being selective ligands for GABAA receptors, in particular having high affinity for the α2 and/or α3 and/or α5 subunit thereof, are accordingly of benefit in the treatment and/or prevention of adverse conditions of the central nervous system, including anxiety, convulsions and cognitive disorders.

  一类吡啶嗪衍生物，其在4位被取代的杂环芳香环可选择地被取代，是GABAA受体的选择性配体，特别是具有对其α2和/或α3和/或α5亚基的高亲和力，因此有助于治疗和/或预防中枢神经系统的不良状况，包括焦虑、惊厥和认知障碍。
• Phenylpyridazine derivatives as ligands for gaba receptors
  申请人：Blackaby Wesley

  公开号：US20060235021A1

  公开（公告）日：2006-10-19

  A class of 4-phenylpyridazine derivatives of Formula (I), being selective ligands for GABA A receptors, in particular having high affinity for the α2 and/or α3 and or α5 subunit thereof, are accordingly of benefit in the treatment and/or prevention of adverse conditions of the central nervous system, including anxiety, convulsions and cognitive disorders.

  一类4-苯基吡嗪衍生物(I式)，是选择性的GABAA受体配体，特别是具有高亲和力的α2和/或α3和/或α5亚单位，因此对于治疗和/或预防中枢神经系统的不良病症，包括焦虑，惊厥和认知障碍具有益处。
• Pyridazine derivatives as ligands for GABA receptors
  申请人：Merck Sharp & Dohme Ltd.

  公开号：US07381725B2

  公开（公告）日：2008-06-03

  A class of pyridazine derivatives, substituted in the 4-position by an optionally substituted heteroaromatic ring, being selective ligands for GABAA receptors, in particular having high affinity for the α2 and/or α3 and/or α5 subunit thereof, are accordingly of benefit in the treatment and/or prevention of adverse conditions of the central nervous system, including anxiety, convulsions and cognitive disorders.

  一类吡啶嗪衍生物，其在4位被一个可选取代的杂环芳香环所取代，是选择性的GABAA受体配体，特别是具有高亲和力的α2和/或α3和/或α5亚基，因此对于治疗和/或预防中枢神经系统的不良状况，包括焦虑、惊厥和认知障碍具有益处。