3-methyl-5,6,7,8-tetrahydro-1H-[1,2,4]triazolo[1,2-a]pyridazine-1-thione | 1450819-93-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 3-methyl-5,6,7,8-tetrahydro-1H-[1,2,4]triazolo[1,2-a]pyridazine-1-thione
• CAS: 1450819-93-8
• 化学式: C₇H₁₁N₃S
• 分子量: 169.25
• InChiKey: HXNQJIBDDXANQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  22.75
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-methyl-5,6,7,8-tetrahydro-1H-[1,2,4]triazolo[1,2-a]pyridazine-1-thione 在 sodium tetrahydroborate 作用下， 以 异丙醇 为溶剂， 反应 24.0h， 以17%的产率得到3-methyl-2,3,5,6,7,8-hexahydro-1H-[1,2,4]-triazolo[1,2-a]pyridazine-1-thione
  参考文献：
  名称：

  Investigations on synthesis and structure elucidation of novel [1,2,4]triazolo[1,2-a]pyridazine-1-thiones and their inhibitory activity against inducible nitric oxide synthase

  摘要：

  The inducible nitric oxide synthase (iNOS) is a target of great research interest due to its importance in a number of diseases, for example, septic shock and inflammatory lung diseases. A variety of 3-substituted [1,2,4]triazolo[1,2-a]pyridazine derivatives was synthesized by ring closure with hexahydropyridazinel-1-carbothioamide by using aliphatic and aromatic aldehydes. The activity of the new substances was tested on the insulin-secreting rat insulinoma cell line RINm5F. iNOS was expressed through exposure to interleukin-1 beta (IL-1 beta) and interferon-gamma (IFN-gamma). A number of the investigated compounds were more active than the reference inhibitor aminoguanidine (AG). Structure-activity relationships showed that a phenyl substituent in position 3 is apparently essential for inhibition. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.064
• 作为产物：
  描述：

  N-[(2-acetyl-1,2,3,4,5,6-hexahydropyridazine-1-yl)thiocarbonyl]ethanamide 在 对甲苯磺酸 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以60%的产率得到3-methyl-5,6,7,8-tetrahydro-1H-[1,2,4]triazolo[1,2-a]pyridazine-1-thione
  参考文献：
  名称：

  Investigations on synthesis and structure elucidation of novel [1,2,4]triazolo[1,2-a]pyridazine-1-thiones and their inhibitory activity against inducible nitric oxide synthase

  摘要：

  The inducible nitric oxide synthase (iNOS) is a target of great research interest due to its importance in a number of diseases, for example, septic shock and inflammatory lung diseases. A variety of 3-substituted [1,2,4]triazolo[1,2-a]pyridazine derivatives was synthesized by ring closure with hexahydropyridazinel-1-carbothioamide by using aliphatic and aromatic aldehydes. The activity of the new substances was tested on the insulin-secreting rat insulinoma cell line RINm5F. iNOS was expressed through exposure to interleukin-1 beta (IL-1 beta) and interferon-gamma (IFN-gamma). A number of the investigated compounds were more active than the reference inhibitor aminoguanidine (AG). Structure-activity relationships showed that a phenyl substituent in position 3 is apparently essential for inhibition. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.064