N-(4-aminobutyl)-2-(tritylthio)acetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-(4-aminobutyl)-2-(tritylthio)acetamide
• 英文别名: N-(4-Amino-butyl)-2-tritylsulfanyl-acetamide；N-(4-aminobutyl)-2-tritylsulfanylacetamide
• 化学式: C₂₅H₂₈N₂OS
• 分子量: 404.576
• InChiKey: QUODHZVJSDHYSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-aminobutyl)-2-(tritylthio)acetamide 在 三乙基硅烷 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 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
• 作为产物：
  描述：

  三苯基甲醇 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 5.0h， 生成 N-(4-aminobutyl)-2-(tritylthio)acetamide
  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

• THIAZOLE COMPOUNDS, METHODS FOR PREPARATION AND USE THEREOF
  申请人：Shanghai Puyi Chemical Co., Ltd.

  公开号：US20140148600A1

  公开（公告）日：2014-05-29

  The present invention relates to thiazole compounds of formula I, the method for preparation and use thereof. More specifically, the present invention relates to novel derivatives of natural product largazole, the method for preparing them and their uses for treatments against tumor and multiple sclerosis as inhibitors of histone deacetylase.

  本发明涉及式I的噻唑化合物，其制备方法和用途。更具体地说，本发明涉及天然产物largazole的新衍生物，其制备方法以及作为组蛋白脱乙酰化酶抑制剂用于抗肿瘤和多发性硬化症治疗的用途。
• 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.
• THIAZOLE COMPOUND AND PREPARATION METHOD AND USE THEREOF
  申请人：Shanghai Theorion Pharmaceutical Co., Ltd.

  公开号：EP2708534B1

  公开（公告）日：2017-07-12
• US9216962B2
  申请人：——

  公开号：US9216962B2

  公开（公告）日：2015-12-22
• 10.1039/d4md00175c
  作者：Guardigni, Melissa、Greco, Giulia、Poeta, Eleonora、Santini, Alan、Tassinari, Elisa、Bergamini, Christian、Zalambani, Chiara、De Simone, Angela、Andrisano, Vincenza、Uliassi, Elisa、Monti, Barbara、Bolognesi, Maria Laura、Fimognari, Carmela、Milelli, Andrea

  DOI：10.1039/d4md00175c

  日期：——