9-bromo-8-oxo-N-phenyl-nonanamide | 885664-75-5

• 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: 9-bromo-8-oxo-N-phenyl-nonanamide
• 英文别名: 9-bromo-8-oxo-N-phenylnonanamide
• CAS: 885664-75-5
• 化学式: C₁₅H₂₀BrNO₂
• 分子量: 326.233
• InChiKey: YHHZGTSUTSBTPG-UHFFFAOYSA-N

物化性质

• 沸点：
  509.6±30.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  19.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  9-bromo-8-oxo-N-phenyl-nonanamide 在 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 6.0h， 生成 8-oxo-N-phenyl-9-sulfanylnonanamide
  参考文献：
  名称：

  Carbonyl- and sulfur-containing analogs of suberoylanilide hydroxamic acid: Potent inhibition of histone deacetylases

  摘要：

  Suberoylanilide hydroxamic acid (SAHA), an inhibitor of histone deacetylase, is used in clinical trials for a variety of advanced cancers. Twelve new analogs of SAHA were synthesized and tested as in vitro inhibitors of isolated histone deacetylases (HDACS) and in vivo inhibitors of interferon regulated transcriptional responses (a marker for HDAC activity). The analogs containing an alpha-mercaptoketone or an alpha-thioacetoxyketone were more potent than SAHA in both assays. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.047
• 作为产物：
  描述：

  8-壬烯酸 在 jones reagent 、 1-羟基苯并三唑 、 溶剂黄146 、 达卡巴嗪 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 、 potassium bromide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.17h， 生成 9-bromo-8-oxo-N-phenyl-nonanamide
  参考文献：
  名称：

  Carbonyl- and sulfur-containing analogs of suberoylanilide hydroxamic acid: Potent inhibition of histone deacetylases

  摘要：

  Suberoylanilide hydroxamic acid (SAHA), an inhibitor of histone deacetylase, is used in clinical trials for a variety of advanced cancers. Twelve new analogs of SAHA were synthesized and tested as in vitro inhibitors of isolated histone deacetylases (HDACS) and in vivo inhibitors of interferon regulated transcriptional responses (a marker for HDAC activity). The analogs containing an alpha-mercaptoketone or an alpha-thioacetoxyketone were more potent than SAHA in both assays. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.047

文献信息

• Trithiocarbonates—Exploration of a new head group for HDAC inhibitors
  作者：Florian Dehmel、Thomas Ciossek、Thomas Maier、Steffen Weinbrenner、Beate Schmidt、Martin Zoche、Thomas Beckers

  DOI：10.1016/j.bmcl.2007.06.063

  日期：2007.9

  class I/II enzymes is a new, promising approach for cancer therapy. In the present study, we disclose a new structural class of HDAC inhibitors with the trithiocarbonate motif. A clear structure-activity-relationship was obtained for the cap-linker motif and the putative Zn(2+) complexing head group. Selected analogs display potent inhibition of HDAC enzymatic activity and a cellular potency comparable

  抑制组蛋白脱乙酰基酶I / II类酶是一种新的，有前途的癌症治疗方法。在本研究中，我们公开了具有三硫代碳酸酯基序的HDAC抑制剂的新结构类别。明确的结构-活性-关系获得了帽连接基序和假定的Zn（2+）络合头基。所选类似物显示出对HDAC酶活性的有效抑制作用，并且具有与最近被批准用于治疗晚期皮肤T细胞淋巴瘤的辛二酰苯胺异羟肟酸（SAHA）相当的细胞效价。