7-(2-Bromo-acetylamino)-heptanoic acid phenylamide | 651767-98-5

• 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: 7-(2-Bromo-acetylamino)-heptanoic acid phenylamide
• 英文别名: 7-[(2-bromoacetyl)amino]-N-phenylheptanamide
• CAS: 651767-98-5
• 化学式: C₁₅H₂₁BrN₂O₂
• 分子量: 341.248
• InChiKey: RZRWMPHWJJGUGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-(2-Bromo-acetylamino)-heptanoic acid phenylamide 在 potassium carbonate 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 7-(2-mercapto-acetylamino)-heptanoic acid phenylamide
  参考文献：
  名称：

  Identification of a potent non-hydroxamate histone deacetylase inhibitor by mechanism-based drug design

  摘要：

  In order to find novel non-hydroxamate histone deacetylase (HDAC) inhibitors, we synthesized several suberoylanilide hydroxamic acid (SAHA)-based compounds designed on the basis of the catalytic mechanism of HDACs. Among these compounds, 5b was found to be as potent as SAHA. Kinetic enzyme assays and molecular modeling suggested that the mercaptoacetamide moiety of 5b interacts with the zinc in the active site of HDACs and removes a water molecule from the reactive site of the deacetylation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.074
• 作为产物：
  描述：

  辛二酸 在 palladium on activated charcoal 二苯基膦叠氮化物 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 生成 7-(2-Bromo-acetylamino)-heptanoic acid phenylamide
  参考文献：
  名称：

  Novel histone deacetylase inhibitors: design, synthesis, enzyme inhibition, and binding mode study of SAHA-Based non-hydroxamates

  摘要：

  In order to find novel non-hydroxamate histone deacetylase (HDAC) inhibitors, a series of compounds modeled after suberoylanilide hydroxamic acid (SAHA) were designed and synthesized as (i) substrate (acetyl lysine) analogues (compounds 3-7), (ii) analogues bearing various functional groups expected to chelate zinc ion (compounds 8-15), and (iii) analogues bearing nucleophilic functional groups which could bind covalently to HDACs (compounds 16-18). In this series, semicarbazide 8b and bromoacetamides 18b,c were found to be potent HDAC inhibitors for non-hydroxamates. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.048