6-(3-benzyl-1,2,4-oxadiazol-5-yl)pyridazin-3-ol | 944808-71-3

• 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-(3-benzyl-1,2,4-oxadiazol-5-yl)pyridazin-3-ol
• 英文别名: 3-(3-benzyl-1,2,4-oxadiazol-5-yl)-1H-pyridazin-6-one
• CAS: 944808-71-3
• 化学式: C₁₃H₁₀N₄O₂
• 分子量: 254.248
• InChiKey: REIFOCQNHDNBIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  80.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(3-benzyl-1,2,4-oxadiazol-5-yl)pyridazin-3-ol 在 三氯氧磷 作用下， 反应 2.0h， 以95%的产率得到3-(3-benzyl-1,2,4-oxadiazol-5-yl)-6-chloropyridazine
  参考文献：
  名称：

  Discovery of Potent, Selective, Orally Bioavailable Stearoyl-CoA Desaturase 1 Inhibitors

  摘要：

  Stearoyl-CoA desaturase 1 (SCD1) catalyzes the committed step in the biosynthesis of monounsaturated fatty acids from saturated, long-chain fatty acids. Studies with SCD1 knockout mice have established that these animals are lean and protected from leptin deficiency-induced and diet-induced obesity, with greater whole body insulin sensitivity than wild-type animals. In this work, we have discovered a series of potent, selective, orally bioavailable SCD1 inhibitors based on a known pyridazine carboxamide template. The representative lead inhibitor 28c also demonstrates excellent cellular activity in blocking the conversion of saturated long-chain fatty acid-CoAs (LCFA-CoAs) to monounsaturated LCFA-CoAs in HepG2 cells.

  DOI：

  10.1021/jm070219p
• 作为产物：
  描述：

  6-羟基-3-哒嗪甲酸 在 N,N-二甲基甲酰胺 氯化亚砜 、 N,N-二异丙基乙胺 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 12.33h， 生成 6-(3-benzyl-1,2,4-oxadiazol-5-yl)pyridazin-3-ol
  参考文献：
  名称：

  Discovery of Potent, Selective, Orally Bioavailable Stearoyl-CoA Desaturase 1 Inhibitors

  摘要：

  Stearoyl-CoA desaturase 1 (SCD1) catalyzes the committed step in the biosynthesis of monounsaturated fatty acids from saturated, long-chain fatty acids. Studies with SCD1 knockout mice have established that these animals are lean and protected from leptin deficiency-induced and diet-induced obesity, with greater whole body insulin sensitivity than wild-type animals. In this work, we have discovered a series of potent, selective, orally bioavailable SCD1 inhibitors based on a known pyridazine carboxamide template. The representative lead inhibitor 28c also demonstrates excellent cellular activity in blocking the conversion of saturated long-chain fatty acid-CoAs (LCFA-CoAs) to monounsaturated LCFA-CoAs in HepG2 cells.

  DOI：

  10.1021/jm070219p

文献信息

• Discovery of Potent, Selective, Orally Bioavailable Stearoyl-CoA Desaturase 1 Inhibitors
  作者：Gang Liu、John K. Lynch、Jennifer Freeman、Bo Liu、Zhili Xin、Hongyu Zhao、Michael D. Serby、Philip R. Kym、Tom S. Suhar、Harriet T. Smith、Ning Cao、Ruojing Yang、Rich S. Janis、Joel A. Krauser、Steven P. Cepa、David W. A. Beno、Hing L. Sham、Christine A. Collins、Teresa K. Surowy、Heidi S. Camp

  DOI：10.1021/jm070219p

  日期：2007.6.1

  Stearoyl-CoA desaturase 1 (SCD1) catalyzes the committed step in the biosynthesis of monounsaturated fatty acids from saturated, long-chain fatty acids. Studies with SCD1 knockout mice have established that these animals are lean and protected from leptin deficiency-induced and diet-induced obesity, with greater whole body insulin sensitivity than wild-type animals. In this work, we have discovered a series of potent, selective, orally bioavailable SCD1 inhibitors based on a known pyridazine carboxamide template. The representative lead inhibitor 28c also demonstrates excellent cellular activity in blocking the conversion of saturated long-chain fatty acid-CoAs (LCFA-CoAs) to monounsaturated LCFA-CoAs in HepG2 cells.