N-hexadecyl-2-hydroxybenzamide

• 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: N-hexadecyl-2-hydroxybenzamide
• 英文别名: N-hexadecylsalicylamide
• 化学式: C₂₃H₃₉NO₂
• 分子量: 361.568
• InChiKey: VQLKICSMSHRLMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  26
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  十六胺 、 水杨酸 在 (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 N-hexadecyl-2-hydroxybenzamide
  参考文献：
  名称：

  脂质过氧化抑制研究：1,3-二（[[1,1'-联苯] -3-基）脲的有前途的案例。

  摘要：

  在本研究中，使用脂质过氧化（LP）方法研究了18种内源性大麻素系统水解酶抑制剂的抗氧化活性。在被测定的化合物中，有十种属于氨基甲酸酯，与苯基[1,1'-联苯] -3-基氨基甲酸酯（6）首次报道，而八种是棕榈胺的逆酰胺衍生物。有趣的是，结果表明大多数被测化合物具有良好的抗氧化性能。特别是，1,3-二（[[1,1'-联苯] -3-基）脲（3）的IC 50  = 26±6μM，可与标准抗氧化剂trolox和槲皮素获得的酮相比较（IC 50  = 22±6） μM和23±6μM）。化合物3通过从头算来进一步研究，以阐明抗氧化作用的可能机理。为了估计3作为自由基清除剂的能力，在B3LYP / 6–311 ++ G⁄⁄水平上优化了结构，并计算了各自的键解离焓。在非极性介质中的计算预测了将氢原子赠予自由基并形成N中心自由基的有利机理，而在极性溶剂中的计算则是通过SPLET取代HAT H吸收清除自由基的机

  DOI：

  10.1016/j.cbi.2020.109137

文献信息

• Development of new inhibitors for N-acylethanolamine-hydrolyzing acid amidase as promising tool against bladder cancer
  作者：Riccardo Vago、Arianna Bettiga、Andrea Salonia、Pierangela Ciuffreda、Roberta Ottria

  DOI：10.1016/j.bmc.2016.12.042

  日期：2017.2

  The endocannabinoid system is a signaling system involved in a wide range of biological effects. Literature strongly suggests the endocannabinoid system role in the pathogenesis of cancer and that its pharmacological activation produces therapeutic benefits. Last research promotes the endocannabinoid system modulation by inhibition of endocannabinoids hydrolytic enzymes instead of direct activation of endocannabinoid receptors to avoid detrimental effects on cognition and motor control. Here we report the identification of N-acylethanolamine-hydrolyzing acid amidase (NAAA) inhibitors able to reduce cell proliferation and migration and cause cell death on different bladder cancer cell lines. These molecules were designed, synthesized and characterized and active compounds were selected by a fluorescence high-throughput screening method set-up on human recombinant NAAA that also allows to characterize the mechanism of inhibition. Together our results suggest an important role for NAAA in cell migration and in inducing tumor cell death promoting this enzyme as pharmacological target against bladder cancer. (C) 2016 Elsevier Ltd. All rights reserved.
• Lipase-Catalyzed Solvent-Free Amidation of Phenolic Acids
  作者：Parshant Kaushik、Najam Akhtar Shakil、Jitendra Kumar、Braj Bhushan Singh

  DOI：10.1080/00397911.2014.974611

  日期：2015.3.4

  A series of N-alkyl-substituted amides, based on various phenolic acids, have been synthesized by the condensation of equimolar amounts of phenolic acids with different alkyl amines in the presence of Candida antarctica lipase at 60-90 degrees C in 16-20 h. The reactions were carried out in a solvent-free system without the use of any activating agents. All the products were obtained in appreciable amounts and the yields for different compounds varied between 75.6% and 83.5%. The synthesized compounds were characterized using spectroscopy techniques, namely infrared and NMR (H-1 and C-13).