4-ethyl-3-methyl-6H-[1,2]oxazolo[3,4-d]pyridazin-7-one

• 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: 4-ethyl-3-methyl-6H-[1,2]oxazolo[3,4-d]pyridazin-7-one
• 化学式: C₈H₉N₃O₂
• 分子量: 179.178
• InChiKey: PPRSJGXVLOETGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  67.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-ethyl-3-methyl-6H-[1,2]oxazolo[3,4-d]pyridazin-7-one 在 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 甲酸铵 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 4-amino-6-ethyl-5-(1-hydroxyethyl)-2-[3-(4-p-tolylpiperazin-1-yl)propyl]pyridazin-3(2H)-one
  参考文献：
  名称：

  Synthesis of five and six-membered heterocycles bearing an arylpiperazinylalkyl side chain as orally active antinociceptive agents

  摘要：

  A number of heterocycles bearing an arylpiperazinylalkyl side chain and structurally related to the previously described lead ET1 (4-amino-6-methyl-2-[3-(4-p-tolylpiperazin-1-yl) propyl]-5-vinylpyridazin-3 (2H)-one) was synthesized and tested for their antinociceptive activity in Writhing Test. Many compounds, tested at doses of 20-40 mg/kg po were able to reduce the number of abdominal constrictions by more than 47% and, in same cases, the potency is comparable to lead ET1 as for 5e, 24a, 27b and 27c. The analgesia induced by the active compounds was completely prevented by pretreatment with alpha(2)-antagonist yohimbine, confirming the involvement of the adrenergic system in the mechanism of action for these new compounds. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.08.043

文献信息

• Synthesis of five and six-membered heterocycles bearing an arylpiperazinylalkyl side chain as orally active antinociceptive agents
  作者：Claudia Vergelli、Giovanna Ciciani、Agostino Cilibrizzi、Letizia Crocetti、Lorenzo Di Cesare Mannelli、Carla Ghelardini、Gabriella Guerrini、Antonella Iacovone、Maria Paola Giovannoni

  DOI：10.1016/j.bmc.2015.08.043

  日期：2015.10

  A number of heterocycles bearing an arylpiperazinylalkyl side chain and structurally related to the previously described lead ET1 (4-amino-6-methyl-2-[3-(4-p-tolylpiperazin-1-yl) propyl]-5-vinylpyridazin-3 (2H)-one) was synthesized and tested for their antinociceptive activity in Writhing Test. Many compounds, tested at doses of 20-40 mg/kg po were able to reduce the number of abdominal constrictions by more than 47% and, in same cases, the potency is comparable to lead ET1 as for 5e, 24a, 27b and 27c. The analgesia induced by the active compounds was completely prevented by pretreatment with alpha(2)-antagonist yohimbine, confirming the involvement of the adrenergic system in the mechanism of action for these new compounds. (C) 2015 Elsevier Ltd. All rights reserved.