(E)-4-((4-phenylpiperazin-1-ylimino)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: (E)-4-((4-phenylpiperazin-1-ylimino)methyl)benzene-1,2-diol
• 英文别名: 4-[(E)-(4-phenylpiperazin-1-yl)iminomethyl]benzene-1,2-diol
• 化学式: C₁₇H₁₉N₃O₂
• 分子量: 297.357
• InChiKey: SVDSQTDJNMFDDT-QGOAFFKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  59.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-亚硝基-4-苯基-哌嗪 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.5h， 生成 (E)-4-((4-phenylpiperazin-1-ylimino)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

• MODULATION OF ADIPOSE TRIGLYCERIDE LIPASE FOR PREVENTION AND TREATMENT OF CACHEXIA, LOSS OF WEIGHT AND MUSCLE ATROPHY AND METHODS OF SCREENING THEREFOR
  申请人：Zimmerman Robert

  公开号：US20120230943A1

  公开（公告）日：2012-09-13

  The present invention relates to agents, and methods for identifying compounds, which agents and compounds are effective in the treatment, and more particularly, that inhibit cachexia, and its associated or related disorders and conditions. In addition, the invention relates to compositions and methods for the use thereof in treating conditions that are characterized by cachexia, and its associated or related disorders and conditions and/or cachexia, and its associated or related disorders and conditions, such as for example, cancer cachexia and cachexia associated with AIDS, autoimmune disorders, drug addiction, alcoholism, chronic inflammatory disorders, cirrhosis of the liver, anorexia and neurodegenerative disease. In particular, the diagnostic marker and drug target of the invention is the ATGL Lipase, which can be inhibited by e.g. siRNAs and compounds with any of the following structures (I).
• US8993509B2
  申请人：——

  公开号：US8993509B2

  公开（公告）日：2015-03-31
• [EN] MODULATION OF ADIPOSE TRIGLYCERIDE LIPASE FOR PREVENTION AND TREATMENT OF CACHEXIA, LOSS OF WEIGHT AND MUSCLE ATROPHY AND METHODS OF SCREENING THEREFOR<br/>[FR] MODULATION DE L'ADIPOSE TRIGLYCÉRIDE LIPASE POUR PRÉVENIR ET TRAITER LA CACHEXIE, LA PERTE DE POIDS ET L'ATROPHIE MUSCULAIRE ET PROCÉDÉS DE CRIBLAGE À DES FINS D'IDENTIFICATION
  申请人：ZIMMERMANN ROBERT

  公开号：WO2010115825A2

  公开（公告）日：2010-10-14

  The present invention relates to agents, and methods for identifying compounds, which agents and compounds are effective in the treatment, and more particularly, that inhibit cachexia, and its associated or related disorders and conditions. In addition, the invention relates to compositions and methods for the use thereof in treating conditions that are characterized by cachexia, and its associated or related disorders and conditions and/or cachexia, and its associated or related disorders and conditions, such as for example, cancer cachexia and cachexia associated with AIDS, autoimmune disorders, drug addiction, alcoholism, chronic inflammatory disorders, cirrhosis of the liver, anorexia and neurodegenerative disease. In particular, the diagnostic marker and drug target of the invention is the ATGL Lipase, which can be inhibited by e.g. siRNAs and compounds with any of the following structures (I).
• 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/).