4-((4-phenylpiperazin-1-yl)methyl)benzene-1,2-diol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-((4-phenylpiperazin-1-yl)methyl)benzene-1,2-diol
• 英文别名: 4-[(4-Phenylpiperazin-1-yl)methyl]benzene-1,2-diol；4-[(4-phenylpiperazin-1-yl)methyl]benzene-1,2-diol
• 化学式: C₁₇H₂₀N₂O₂
• 分子量: 284.358
• InChiKey: VPERQCBGSXRUIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-苯基哌嗪 、 3,4-二羟基苯甲醛 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 以26%的产率得到4-((4-phenylpiperazin-1-yl)methyl)benzene-1,2-diol
  参考文献：
  名称：

  Structure–activity studies in the development of a hydrazone based inhibitor of adipose-triglyceride lipase (ATGL)

  摘要：

  Adipose triglyceride lipase (ATGL) catalyzes the degradation of cellular triacylglycerol stores and strongly determines the concentration of circulating fatty acids (FAs). High serum FA levels are causally linked to the development of insulin resistance and impaired glucose tolerance, which eventually progresses to overt type 2 diabetes. ATGL-specific inhibitors could be used to lower circulating FAs, which can counteract the development of insulin resistance. In this article, we report about structure-activity relationship (SAR) studies of small molecule inhibitors of ATGL based on a hydrazone chemotype. The SAR indicated that the binding pocket of ATGL requests rather linear compounds without bulky substituents. The best inhibitor showed an IC50 = 10 mu M in an assay with COS7-cell lysate overexpressing murine ATGL. (C) 2015 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/).

  DOI：

  10.1016/j.bmc.2015.02.051

文献信息

• Structure–activity studies in the development of a hydrazone based inhibitor of adipose-triglyceride lipase (ATGL)
  作者：Nicole Mayer、Martina Schweiger、Michaela-Christina Melcher、Christian Fledelius、Rudolf Zechner、Robert Zimmermann、Rolf Breinbauer

  DOI：10.1016/j.bmc.2015.02.051

  日期：2015.6

  Adipose triglyceride lipase (ATGL) catalyzes the degradation of cellular triacylglycerol stores and strongly determines the concentration of circulating fatty acids (FAs). High serum FA levels are causally linked to the development of insulin resistance and impaired glucose tolerance, which eventually progresses to overt type 2 diabetes. ATGL-specific inhibitors could be used to lower circulating FAs, which can counteract the development of insulin resistance. In this article, we report about structure-activity relationship (SAR) studies of small molecule inhibitors of ATGL based on a hydrazone chemotype. The SAR indicated that the binding pocket of ATGL requests rather linear compounds without bulky substituents. The best inhibitor showed an IC50 = 10 mu M in an assay with COS7-cell lysate overexpressing murine ATGL. (C) 2015 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/).