5-Mercapto-pentanoic acid phenylamide | 670233-81-5

• 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: 5-Mercapto-pentanoic acid phenylamide
• 英文别名: Pentanamide, 5-mercapto-N-phenyl-；N-phenyl-5-sulfanylpentanamide
• CAS: 670233-81-5
• 化学式: C₁₁H₁₅NOS
• 分子量: 209.312
• InChiKey: AGRMYYLOBIRRKQ-UHFFFAOYSA-N

物化性质

• 熔点：
  120-121 °C
• 沸点：
  407.6±28.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  30.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-溴戊酸 在 草酰氯 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.25h， 生成 5-Mercapto-pentanoic acid phenylamide
  参考文献：
  名称：

  β-Cyclodextrin Host−Guest Complexes Probed under Thermodynamic Equilibrium:  Thermodynamics and AFM Force Spectroscopy

  摘要：

  The rupture forces of individual host-guest complexes between beta-cycloclextrin (beta-CD) heptathioether monolayers on Au(111) and several surface-confined guests were measured in aqueous medium by single molecule force spectroscopy using an atomic force microscope. Anilyl, toluidyl, tert-butylphenyl, and adamantylthiols (0.2-1%) were immobilized in mixed monolayers with 2-mercaptoethanol on gold-coated AFM tips. For all guests and for all surface coverages, the force-displacement curves measured between the functionalized tips and monolayers of beta-CD exhibited single, as well as multiple, pull-off events. The histograms of the pull-off forces showed several maxima at equidistant forces, with force quanta characteristic for each guest of 39 +/- 15, 45 +/- 15, 89 +/- 15, and 102 +/- 15 pN, respectively. These force quanta were independent of the loading rate, indicating that, because of the fast complexation/ decomplexation kinetics, the rupture forces were probed under thermodynamic equilibrium. The force values followed the same trend as the free binding energy DeltaG(o) measured for model guest compounds in solution or on beta-CD monolayers, as determined by microcalorimetry and surface plasmon resonance measurements, respectively. A descriptive model was developed to correlate quantitatively the pull-off force values with the DeltaG(o) of the complexes, based on the evaluation of the energy potential landscape of tip-surface interaction.

  DOI：

  10.1021/ja0383569

文献信息

• Novel Inhibitors of Human Histone Deacetylases:  Design, Synthesis, Enzyme Inhibition, and Cancer Cell Growth Inhibition of SAHA-Based Non-hydroxamates
  作者：Takayoshi Suzuki、Yuki Nagano、Akiyasu Kouketsu、Azusa Matsuura、Sakiko Maruyama、Mineko Kurotaki、Hidehiko Nakagawa、Naoki Miyata

  DOI：10.1021/jm049207j

  日期：2005.2.1

  To find novel non-hydroxamate histone deacetylase (HDAC) inhibitors, a series of compounds modeled after suberoylanilide hydroxamic acid (SAHA) was designed and synthesized. In this series, compound 7, in which the hydroxamic acid of SAHA is replaced by a thiol, was found to be as potent as SAHA, and optimization of this series led to the identification of HDAC inhibitors more potent than SAHA. In cancer

  为了找到新型的非异羟肟酸酯组蛋白脱乙酰基酶（HDAC）抑制剂，设计并合成了以亚磺酰苯胺异羟肟酸（SAHA）为模型的一系列化合物。在该系列中，发现化合物7（其中SAHA的异羟肟酸被硫醇替代）与SAHA一样有效，该系列的优化导致鉴定出比SAHA更有效的HDAC抑制剂。在癌细胞生长抑制测定中，S-异丁酰基衍生物51显示出强活性，并且其效力与SAHA相当。通过Western印迹分析证实癌细胞生长抑制活性是组蛋白过度乙酰化和随后诱导p21（WAF1 / CIP1）的结果。
• Thiol-based SAHA analogues as potent histone deacetylase inhibitors
  作者：Takayoshi Suzuki、Akiyasu Kouketsu、Azusa Matsuura、Arihiro Kohara、Shin-ichi Ninomiya、Kohfuku Kohda、Naoki Miyata

  DOI：10.1016/j.bmcl.2004.03.063

  日期：2004.6

  In order to find novel nonhydroxamate histone deacetylase (HDAC) inhibitors, a series of thiol-based compounds modeled after suberoylanilide hydroxamic acid (SAHA) was synthesized, and their inhibitory effect on HDACs was evaluated. Compound 6, in which the hydroxamic acid of SAHA was replaced by a thiol, was found to be as potent as SAHA, and optimization of this series led to the identification of HDAC inhibitors more potent than SAHA. (C) 2004 Elsevier Ltd. All rights reserved.