4-Dimethylamino-N-[4-(2-mercapto-acetylamino)-butyl]-benzamide | 828920-05-4

• 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: 4-Dimethylamino-N-[4-(2-mercapto-acetylamino)-butyl]-benzamide
• 英文别名: 4-(Dimethylamino)-N-[4-(2-sulfanylacetamido)butyl]benzamide；4-(dimethylamino)-N-[4-[(2-sulfanylacetyl)amino]butyl]benzamide
• CAS: 828920-05-4
• 化学式: C₁₅H₂₃N₃O₂S
• 分子量: 309.433
• InChiKey: BTMXKFKUNIPMAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  62.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-(dimethylamino)-N-[4-[(2-tritylsulfanylacetyl)amino]butyl]benzamide 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-Dimethylamino-N-[4-(2-mercapto-acetylamino)-butyl]-benzamide
  参考文献：
  名称：

  Functional Differences in Epigenetic ModulatorsSuperiority of Mercaptoacetamide-Based Histone Deacetylase Inhibitors Relative to Hydroxamates in Cortical Neuron Neuroprotection Studies

  摘要：

  We compare the ability of two structurally different classes of epigenetic modulators, namely, histone deacetylase (HDAC) inhibitors containing either a hydroxamate or a mercaptoacetamide as the zinc binding group, to protect cortical neurons in culture from oxidative stress-induced death. This study reveals that some of the mercaptoacetamide-based HDAC inhibitors are fully protective, whereas the hydroxamates show toxicity at higher concentrations. Our present results appear to be consistent with the possibility that the mercaptoacetamide-based HDAC inhibitors interact with a different subset of the HDAC isozymes [less activity at HDAC1 and 2 correlates with less inhibitor toxicity], or alternatively, are interacting selectively with only the cytoplasmic HDACs that are crucial for protection from oxidative stress.

  DOI：

  10.1021/jm070178x

文献信息

• Histone deacetylase inhibitors and methods of use thereof
  申请人：Kozikowski P. Alan

  公开号：US20050032831A1

  公开（公告）日：2005-02-10

  One aspect of the invention relates to HDAC inhibitors. Methods of sensitizing a cancer cell to the cytotoxic effects of radiotherapy are also provided. The invention also provides methods for treating cancer and methods for treating neurological diseases. Additionally, the invention further provides pharmaceutical compositions comprising an HDAC inhibitor of the invention, and kits comprising a container containing an HDAC inhibitor of the invention.

  这项发明的一个方面涉及HDAC抑制剂。还提供了一种使癌细胞对放疗的细胞毒作用敏感的方法。该发明还提供了治疗癌症和治疗神经疾病的方法。此外，该发明还提供了包含该发明的HDAC抑制剂的药物组合物，以及包含一个容器，其中含有该发明的HDAC抑制剂的试剂盒。
• Histone Deacetylase Inhibitors and Methods of Use Thereof
  申请人：Kozikowski Alan P.

  公开号：US20090163543A1

  公开（公告）日：2009-06-25

  One aspect of the invention relates to HDAC inhibitors. Methods of sensitizing a cancer cell to the cytotoxic effects of radiotherapy are also provided. The invention also provides methods for treating cancer and methods for treating neurological diseases. Additionally, the invention further provides pharmaceutical compositions comprising an HDAC inhibitor of the invention, and kits comprising a container containing an HDAC inhibitor of the invention.

  本发明的一个方面涉及HDAC抑制剂。还提供了增敏癌细胞对放疗细胞毒作用的方法。本发明还提供了治疗癌症和治疗神经疾病的方法。此外，本发明还提供了包含本发明的HDAC抑制剂的制药组合物，以及包含一个容器的套件，其中包含本发明的HDAC抑制剂。
• Chemistry and biology of mercaptoacetamides as novel histone deacetylase inhibitors
  作者：Bin Chen、Pavel A. Petukhov、Mira Jung、Alfredo Velena、Elena Eliseeva、Anatoly Dritschilo、Alan P. Kozikowski

  DOI：10.1016/j.bmcl.2005.01.006

  日期：2005.3

  A series of mercaptoacetamides were designed and synthesized as novel histone deacetylase inhibitors with the aid of modeling. Their ability to inhibit HDAC activity and their effects on cancer cell growth were investigated. Some compounds exhibit better HDAC inhibitory activity than SAHA. (c) 2005 Elsevier Ltd. All rights reserved.
• HISTONE DEACETYLASE INHIBITORS AND METHODS OF USE THEREOF
  申请人：GEORGETOWN UNIVERSITY

  公开号：EP1644323A2

  公开（公告）日：2006-04-12
• EP1644323A4
  申请人：——

  公开号：EP1644323A4

  公开（公告）日：2007-06-20