N-(6-aminohexyl)-2-tritylsulfanyl acetamide | 944457-69-6

• 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-(6-aminohexyl)-2-tritylsulfanyl acetamide
• CAS: 944457-69-6
• 化学式: C₂₇H₃₂N₂OS
• 分子量: 432.63
• InChiKey: HYMOJUIYFNOBBF-UHFFFAOYSA-N

物化性质

• 沸点：
  604.4±55.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  31.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.12
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(6-aminohexyl)-2-tritylsulfanyl acetamide 在 三乙基硅烷 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 生成 2-Mercapto-N-[6-(2-mercapto-acetylamino)-hexyl]-acetamide
  参考文献：
  名称：

  Chemistry and biology of mercaptoacetamides as novel histone deacetylase inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2005.01.006
• 作为产物：
  描述：

  三苯基甲醇 在 三氟乙酸 作用下， 生成 N-(6-aminohexyl)-2-tritylsulfanyl acetamide
  参考文献：
  名称：

  Chemistry and biology of mercaptoacetamides as novel histone deacetylase inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2005.01.006

文献信息

• Functional Differences in Epigenetic ModulatorsSuperiority of Mercaptoacetamide-Based Histone Deacetylase Inhibitors Relative to Hydroxamates in Cortical Neuron Neuroprotection Studies
  作者：Alan P. Kozikowski、Yufeng Chen、Arsen Gaysin、Bin Chen、Melissa A. D'Annibale、Carla M. Suto、Brett C. Langley

  DOI：10.1021/jm070178x

  日期：2007.6.1

  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.
• A Series of Potent and Selective, Triazolylphenyl-Based Histone Deacetylases Inhibitors with Activity against Pancreatic Cancer Cells and <i>Plasmodium falciparum</i>
  作者：Yufeng Chen、Miriam Lopez-Sanchez、Doris N. Savoy、Daniel D. Billadeau、Geoffrey S. Dow、Alan P. Kozikowski

  DOI：10.1021/jm701606b

  日期：2008.6.1

  The discovery of the rules governing the inhibition of the various HDAC isoforms is likely to be key to identifying improved therapeutics that act as epigenetic modulators of gene transcription. Herein we present results on the modification of the CAP region of a set of triazolylphenyl-based HDACIs, and show that the nature of substitution on the phenyl ring plays a role in their selectivity for HDAC1 versus HDAC6, with low to moderate selectivity (2-51-fold) being achieved. In light of the valuable selectivity and potency that were identified for the triazolylphenyl ligand 6b in the inhibition of HDAC6 (IC50 = 1.9 nM), this compound represents a valuable research tool and a candidate for further chemical modifications. Lastly, these new HDACIs were studied for both their anticancer and antimalarial activity, which serve to validate the superior activity of the HDACI 10c.