N-[4-cyano-3-(trifluoromethyl)phenyl]-5-(dithiolan-3-yl)pentanamide | 1357565-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: N-[4-cyano-3-(trifluoromethyl)phenyl]-5-(dithiolan-3-yl)pentanamide
• CAS: 1357565-51-5
• 化学式: C₁₆H₁₇F₃N₂OS₂
• 分子量: 374.451
• InChiKey: CZNRNCKTNBYHPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-氨基-2-三氟甲基苯甲腈 、 Thioctic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 0.58h， 以46%的产率得到N-[4-cyano-3-(trifluoromethyl)phenyl]-5-(dithiolan-3-yl)pentanamide
  参考文献：
  名称：

  A comparative assessment of α-lipoic acid N-phenylamides as non-steroidal androgen receptor antagonists both on and off gold nanoparticles

  摘要：

  A group of alpha-lipoic acid N-phenylamides were synthesized employing a variety of amide coupling protocols utilizing electron deficient anilines. These compounds were then assessed for their ability to block androgen-stimulated proliferation of a human prostate cancer cell line, LNCaP. These structurally simple compounds displayed anti-proliferative activities at, typically, 5-20 mu M concentrations and were comparable to a commonly used anti-androgen Bicalutamide (R). The inclusion of a disulfide (RS-SR) moiety, serving as an anchor to several metal nanoparticle systems (Au, Ag, Fe2O3, etc.), does not impede any biological activity. Conjugation of these compounds to a gold nanoparticle surface resulted in a high degree of cellular toxicity, attributed to the absence of a biocompatible group such as PEG within the organic scaffold. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2011.11.007

文献信息

• A comparative assessment of α-lipoic acid N-phenylamides as non-steroidal androgen receptor antagonists both on and off gold nanoparticles
  作者：Luke C. Henderson、Jarrad M. Altimari、Gail Dyson、Linden Servinis、Birunthi Niranjan、Gail P. Risbridger

  DOI：10.1016/j.bioorg.2011.11.007

  日期：2012.2

  A group of alpha-lipoic acid N-phenylamides were synthesized employing a variety of amide coupling protocols utilizing electron deficient anilines. These compounds were then assessed for their ability to block androgen-stimulated proliferation of a human prostate cancer cell line, LNCaP. These structurally simple compounds displayed anti-proliferative activities at, typically, 5-20 mu M concentrations and were comparable to a commonly used anti-androgen Bicalutamide (R). The inclusion of a disulfide (RS-SR) moiety, serving as an anchor to several metal nanoparticle systems (Au, Ag, Fe2O3, etc.), does not impede any biological activity. Conjugation of these compounds to a gold nanoparticle surface resulted in a high degree of cellular toxicity, attributed to the absence of a biocompatible group such as PEG within the organic scaffold. (C) 2011 Elsevier Inc. All rights reserved.