heptanedioyl aniline hydroxamic acid | 149647-77-8

• 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: heptanedioyl aniline hydroxamic acid
• 英文别名: TSA；US9751832, Tsa；N'-hydroxy-N-phenylheptanediamide
• CAS: 149647-77-8
• 化学式: C₁₃H₁₈N₂O₃
• 分子量: 250.298
• InChiKey: XCELUDLGZVVNON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-phenylcarbamoyl-hexanoic acid ethyl ester 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以75.8%的产率得到heptanedioyl aniline hydroxamic acid
  参考文献：
  名称：

  Design, Synthesis and Biological Evaluation of Hydroxamic Acid Derivatives as Potential High Density Lipoprotein (HDL) Receptor CLA-1 Up-Regulating Agents

  摘要：

  在我们最近的出版物中报道，三氟氯乙酰胺（TSA）和水杨酰胺羟肟酸（SAHA）被发现是新型的人类高密度脂蛋白（HDL）受体CD36和溶酶体整合膜蛋白-II类似物1（CLA-1）的上调剂。作为更全面探索CLA-1上调剂结构-活性关系（SAR）的一部分，我们合成了一系列羟肟酸衍生物，并在HepG2细胞中评估了它们的CLA-1上调活性。某些化合物在10 μg/mL浓度下表现出超过10倍的CLA-1表达上调。化合物1g展现出最佳效力，其EC50低于TSA（EC50 = 0.32 μM对比1.2 μM）。这些化合物提供了早期的新CLA-1上调剂，具有治疗动脉粥样硬化的潜力。

  DOI：

  10.3390/molecules16119178

文献信息

• SELECTIVE HISTONE DEACTYLASE 6 INHIBITORS
  申请人：H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.

  公开号：US20170369428A1

  公开（公告）日：2017-12-28

  Disclosed are selective histone deactylase inhibitors (HDACi) that having Formula I. Methods of making and using these inhibitors for the treatment of cancer, in particular melanoma are also disclosed.
• COMPOUNDS AND METHODS FOR IMPROVING IMPAIRED ENDOGENOUS FIBRINOLYSIS USING HISTONE DEACETYLASE INHIBITORS
  申请人：Cereno Scientific AB

  公开号：US20210060014A1

  公开（公告）日：2021-03-04

  There is provided a compound which is a histone deacetylase (HDAC) inhibitor, or a pharmaceutically acceptable ester, amide, solvate or salt thereof, for use in: (I) treating or preventing a pathological condition associated with excess fibrin deposition and/or thrombus formation; and/or (II) potentiating the degradation of fibrin deposits and preventing such deposits associated with pathological conditions or which may lead to such conditions, wherein the HDAC inhibitor, and the dose thereof, is as described in the description. There is also provided valproic acid, or a pharmaceutically acceptable salt thereof, for use in improving or normalizing endogenous fibrinolysis impaired by local or systemic inflammation.
• Design, Synthesis and Biological Evaluation of Hydroxamic Acid Derivatives as Potential High Density Lipoprotein (HDL) Receptor CLA-1 Up-Regulating Agents
  作者：Xiaofang Chen、Li Wang、Yu Du、Yanbin Wu、Xiaojian Jia、Yuan Yang、Bin Hong

  DOI：10.3390/molecules16119178

  日期：——

  Trichostatin A (TSA) and suberoylanilide hydroxamic acid (SAHA) were reported in our recent publication as novel human high density lipoprotein (HDL) receptor CD36 and Lysosomal integral membrane protein-II Analogous-1 (CLA-1) up-regulators. As part of a broader effort to more fully explore the structure-activity relationships (SAR) of CLA-1 up-regulators, we synthesized a series of hydroxamic acid derivatives and evaluated their CLA-1 up-regulating activities in HepG2 cells. Some compounds exhibited over 10-fold up-regulation of CLA-1 expression in HepG2 cells at 10 μg/mL concentration. The compound 1g showed the best potency, with a lower EC50 than TSA (EC50 = 0.32 μM versus 1.2 μM). These compounds provide early new CLA-1 up-regulators with potential for treating atherosclerosis.

  在我们最近的出版物中报道，三氟氯乙酰胺（TSA）和水杨酰胺羟肟酸（SAHA）被发现是新型的人类高密度脂蛋白（HDL）受体CD36和溶酶体整合膜蛋白-II类似物1（CLA-1）的上调剂。作为更全面探索CLA-1上调剂结构-活性关系（SAR）的一部分，我们合成了一系列羟肟酸衍生物，并在HepG2细胞中评估了它们的CLA-1上调活性。某些化合物在10 μg/mL浓度下表现出超过10倍的CLA-1表达上调。化合物1g展现出最佳效力，其EC50低于TSA（EC50 = 0.32 μM对比1.2 μM）。这些化合物提供了早期的新CLA-1上调剂，具有治疗动脉粥样硬化的潜力。