N-(3-aminopropyl)-2-tritylsulfanylacetamide | 465545-79-3

• 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-(3-aminopropyl)-2-tritylsulfanylacetamide
• CAS: 465545-79-3
• 化学式: C₂₄H₂₆N₂OS
• 分子量: 390.549
• InChiKey: BQSHRWPCZXJCRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 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-(3-aminopropyl)-2-tritylsulfanylacetamide 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 Biphenyl-4-carboxylic acid [3-(2-mercapto-acetylamino)-propyl]-amide
  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-(3-aminopropyl)-2-tritylsulfanylacetamide
  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

• A practical approach to the synthesis of hairpin polyamide–peptide conjugates through the use of a safety-catch linker
  作者：Daniela Fattori、Olaf Kinzel、Paolo Ingallinella、Elisabetta Bianchi、Antonello Pessi

  DOI：10.1016/s0960-894x(02)00122-1

  日期：2002.4

  sequence selective DNA binders. The use of a safety-catch linker for the solid phase synthesis of hairpin polyamides allows for easy preparation of derivatives ready for chemoselective ligation with unprotected peptides. Examples of ligations reported include thioether bond formation and thioester-mediated amide bond formation ('Native Chemical Ligation').

  发夹聚酰胺是高亲和力的，序列选择性的DNA结合剂。使用安全捕获接头用于发夹聚酰胺的固相合成可轻松制备易于与未保护的肽进行化学选择性连接的衍生物。报道的连接的例子包括硫醚键形成和硫酯介导的酰胺键形成（“天然化学连接”）。
• US7507828B2
  申请人：——

  公开号：US7507828B2

  公开（公告）日：2009-03-24
• US8067600B2
  申请人：——

  公开号：US8067600B2

  公开（公告）日：2011-11-29
• 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.
• 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.