6-(2-Bromo-ethyl)-3-methyl-4-phenyl-6H-isoxazolo[3,4-d]pyridazin-7-one | 681828-66-0

• 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: 6-(2-Bromo-ethyl)-3-methyl-4-phenyl-6H-isoxazolo[3,4-d]pyridazin-7-one
• CAS: 681828-66-0
• 化学式: C₁₄H₁₂BrN₃O₂
• 分子量: 334.172
• InChiKey: DDCJSVSRDHMKIF-UHFFFAOYSA-N

物化性质

• 熔点：
  157-159 °C(Solv: ethanol (64-17-5))
• 沸点：
  494.7±55.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  60.92
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-(2-Bromo-ethyl)-3-methyl-4-phenyl-6H-isoxazolo[3,4-d]pyridazin-7-one 在 palladium on activated charcoal 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 5-Acetyl-4-amino-2-(2-morpholin-4-yl-ethyl)-6-phenyl-2H-pyridazin-3-one
  参考文献：
  名称：

  4-Amino-3(2H)-pyridazinones bearing arylpiperazinylalkyl groups and related compounds: synthesis and antinociceptive activity

  摘要：

  A series of 4-amino-3(2H)-pyridazinones substituted at position 2 with arylpiperazinylalkyl groups and analogues were synthesized and their antinociceptive effect was evaluated in the mouse abdominal constriction model. Preliminary SARs studies were performed. Several of the novel compounds dosed at 100 mg/kg s.c. significantly reduced the number of writhes induced by the noxious stimulus. Compound 12e showed 100% inhibition of writhes and was able to protect all the treated animals from the effect of the chemical stimulus. Subsequent dose-response studies revealed 12e to be almost 40-fold more potent than the structurally related Emorfazone.

  DOI：

  10.1016/s0014-827x(03)00162-9
• 作为产物：
  描述：

  1,2-二溴乙烷 、 3-甲基-4-苯基异恶唑并[3,4-d]哒嗪-7(6H)-酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以82%的产率得到6-(2-Bromo-ethyl)-3-methyl-4-phenyl-6H-isoxazolo[3,4-d]pyridazin-7-one
  参考文献：
  名称：

  4-Amino-3(2H)-pyridazinones bearing arylpiperazinylalkyl groups and related compounds: synthesis and antinociceptive activity

  摘要：

  A series of 4-amino-3(2H)-pyridazinones substituted at position 2 with arylpiperazinylalkyl groups and analogues were synthesized and their antinociceptive effect was evaluated in the mouse abdominal constriction model. Preliminary SARs studies were performed. Several of the novel compounds dosed at 100 mg/kg s.c. significantly reduced the number of writhes induced by the noxious stimulus. Compound 12e showed 100% inhibition of writhes and was able to protect all the treated animals from the effect of the chemical stimulus. Subsequent dose-response studies revealed 12e to be almost 40-fold more potent than the structurally related Emorfazone.

  DOI：

  10.1016/s0014-827x(03)00162-9

文献信息

• Isoxazolo-[3,4- d ]-pyridazin-7-(6 H )-ones and their Corresponding 4,5-Disubstituted-3-(2 H )-pyridazinone Analogues as New Substrates for α 1 -Adrenoceptor Selective Antagonists: Synthesis, Modeling, and Binding Studies
  作者：Federica Montesano、Daniela Barlocco、Vittorio Dal Piaz、Amedeo Leonardi、Elena Poggesi、Francesca Fanelli、Piero G. De Benedetti

  DOI：10.1016/s0968-0896(98)00056-x

  日期：1998.7

  A series of phenylpiperazinylalkyl moieties were attached to monocyclic or bicyclic substituted pyridazinones and the new compounds tested for their affinity towards alpha(1)-adrenoceptor and its alpha(1a), alpha(1b) and alpha(1d) subtypes, as well as serotonin S-HT1A receptor. Several analogues (5, 6, 9, and 10) showed remarkable potency and selectivity towards alpha(1a), and alpha(1d) with respect to alpha(1b) subtype. None of the test compounds exhibited significant affinity for 5-HT1A receptor. Finally, on the basis of the alpha(1)-AR subtypes 3D models recently proposed, we have elaborated theoretical interaction models for the new compounds. The theoretical study allowed us to predict the affinity of the new compounds as well as to infer the structural/dynamics determinants of their interaction with the three alpha(1)-AR subtypes. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.