3-(3-phenoxyphenyl)-2,3,5,6,7,8-hexahydro-1H-[1,2,4]triazolo[1,2-a]pyridazine-1-thione | 1450820-14-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(3-phenoxyphenyl)-2,3,5,6,7,8-hexahydro-1H-[1,2,4]triazolo[1,2-a]pyridazine-1-thione
• 英文别名: 1-(3-Phenoxyphenyl)-1,2,5,6,7,8-hexahydro-[1,2,4]triazolo[1,2-a]pyridazine-3-thione；1-(3-phenoxyphenyl)-1,2,5,6,7,8-hexahydro-[1,2,4]triazolo[1,2-a]pyridazine-3-thione
• CAS: 1450820-14-0
• 化学式: C₁₈H₁₉N₃OS
• 分子量: 325.434
• InChiKey: BMJQFQXQDACGLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  59.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  四氢-1(2H)-哒嗪硫代甲酰胺 、 间苯氧基苯甲醛 以 丙酮 为溶剂， 130.0 ℃ 、1.5 MPa 条件下， 反应 0.05h， 以84%的产率得到3-(3-phenoxyphenyl)-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

文献信息

• 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
  作者：Ulrike Schulz、Antje Grossmann、Manja Witetschek、Christian Lemmerhirt、Marcus Polzin、Beate Haertel、Heike Wanka、Olaf Morgenstern

  DOI：10.1016/j.bmc.2013.05.064

  日期：2013.9

  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.