5-phenyl-2H-pyridazin-3-thione

• 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-phenyl-2H-pyridazin-3-thione
• 英文别名: 4-phenyl-1H-pyridazine-6-thione
• 化学式: C₁₀H₈N₂S
• 分子量: 188.253
• InChiKey: ZXGKRJASFQVREF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-phenyl-2H-pyridazin-3-thione 在 Oxone 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 3-(2,4-Difluorophenyl)-1-heptyl-1-[5-(5-phenylpyridazin-3-yl)sulfinylpentyl]urea
  参考文献：
  名称：

  Mono- or Diphenylpyridazines Connected to N-(2,4-Difluorophenyl)-N‘-heptylurea as Acyl-CoA:Cholesterol Acyltransferase Inhibitors

  摘要：

  Mono- and diphenylpyridazine ureido derivatives, structurally related to DuP 128, were synthesized and tested for their inhibitory activity against ACAT isolated from rat liver microsomes. Several compounds displayed ACAT inhibition in the micromolar range. The amino derivatives 4a-c were also tested against hACAT-1 and hACAT-2 isoforms. They retained the same trend shown in the previous assay. Modeling studies on representative terms were performed. Significant similarities between the geometrical features of the model DuP 128 and the most active pyridazine derivatives were observed.

  DOI：

  10.1021/jm050703x
• 作为产物：
  描述：

  5-苯基-3(2H)-吡嗪酮 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以50%的产率得到5-phenyl-2H-pyridazin-3-thione
  参考文献：
  名称：

  Mono- or Diphenylpyridazines Connected to N-(2,4-Difluorophenyl)-N‘-heptylurea as Acyl-CoA:Cholesterol Acyltransferase Inhibitors

  摘要：

  Mono- and diphenylpyridazine ureido derivatives, structurally related to DuP 128, were synthesized and tested for their inhibitory activity against ACAT isolated from rat liver microsomes. Several compounds displayed ACAT inhibition in the micromolar range. The amino derivatives 4a-c were also tested against hACAT-1 and hACAT-2 isoforms. They retained the same trend shown in the previous assay. Modeling studies on representative terms were performed. Significant similarities between the geometrical features of the model DuP 128 and the most active pyridazine derivatives were observed.

  DOI：

  10.1021/jm050703x

文献信息

• Pyridazine derivatives as novel acyl-coa:cholesterol acyltransferase (acat) inhibitors
  作者：Arianna Gelain

  DOI：10.1002/jhet.5570420306

  日期：2005.4

  Acyl-CoA:cholesterol acyltransferase (E.C.2.3.1.26, ACAT) is a microsomial enzyme that catalyses the formation of cholesteryl esters by acylation of cholesterol with long chain fatty acylCoA [1].

  酰基辅酶A：胆固醇酰基转移酶（EC2.3.1.26，ACAT）是一种微粒体酶，可通过将胆固醇与长链脂肪酰基辅酶A酰化来催化胆固醇酯的形成[1]。
• Ureidopyridazine Derivatives as Acyl-CoA: cholesterol acyltransferase Inhibitors
  作者：Arianna Gelain

  DOI：10.3797/scipharm.2006.74.85

  日期：——

  A series of N-(2,4-difluorophenyl)-N’-heptyl-N’-4-[(substituted)-pyridazin-3-yl)thio]pentyl}urea derivatives having a phenyl ring at positions 5 and/or at position 6 of the heterocycle, as well as the corresponding sulfones, were synthesized. Their inhibitory activity against acyl-CoA:cholesterol acyltransferase (ACAT) was tested on the enzyme prepared from rat liver microsomes. Theoretical studies were performed to correlate their activity to their structural features.

  我们合成了一系列 N-(2,4-二氟苯基)-N'-庚基-N'-4-[(取代的)-哒嗪-3-基)硫代]戊基}脲衍生物，这些衍生物的杂环第 5 位和/或第 6 位上有一个苯基环，我们还合成了相应的砜类化合物。在从大鼠肝脏微粒体制备的酶上测试了它们对酰基-CoA：胆固醇酰基转移酶（ACAT）的抑制活性。为了将它们的活性与其结构特征联系起来，还进行了理论研究。
• Mono- or Diphenylpyridazines Connected to <i>N</i>-(2,4-Difluorophenyl)-<i>N</i>‘-heptylurea as Acyl-CoA:Cholesterol Acyltransferase Inhibitors
  作者：Arianna Gelain、Ilaria Bettinelli、Daniela Barlocco、Byoung-Mog Kwon、Tae-Sook Jeong、Kyung-Hyun Cho、Lucio Toma

  DOI：10.1021/jm050703x

  日期：2005.12.1

  Mono- and diphenylpyridazine ureido derivatives, structurally related to DuP 128, were synthesized and tested for their inhibitory activity against ACAT isolated from rat liver microsomes. Several compounds displayed ACAT inhibition in the micromolar range. The amino derivatives 4a-c were also tested against hACAT-1 and hACAT-2 isoforms. They retained the same trend shown in the previous assay. Modeling studies on representative terms were performed. Significant similarities between the geometrical features of the model DuP 128 and the most active pyridazine derivatives were observed.