(R/S)-N-(2-aminophenyl)-2-phenylpropanamide

• 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: (R/S)-N-(2-aminophenyl)-2-phenylpropanamide
• 英文别名: N-(2-aminophenyl)-2-phenylpropionamide；N-(2-aminophenyl)-2-phenylpropanamide
• 化学式: C₁₅H₁₆N₂O
• 分子量: 240.305
• InChiKey: TYIFGBKVFKCIPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R/S)-N-(2-aminophenyl)-2-phenylpropanamide 在 溶剂黄146 作用下， 反应 5.0h， 以87%的产率得到2-(1-phenylethyl)benzimidazole
  参考文献：
  名称：

  将位阻二酰基化的1,2-苯二胺转化为2-取代的苯并咪唑。

  摘要：

  设计了一系列大体积的2-取代的苯并咪唑，以便为几个生物学靶标找到新的潜在客户。由它们的单酰化的对应物通过环脱水形成显示出强烈地依赖于酰基的性质。在二环己基甲基的情况下，仅在对称二酰基化前体的对甲苯磺酸/甲苯混合物中观察到环化。从混合二酰化衍生物开始分析机理。

  DOI：

  10.1248/cpb.53.492
• 作为产物：
  描述：

  2-苯基丙酸 、 邻苯二胺 在 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以72%的产率得到(R/S)-N-(2-aminophenyl)-2-phenylpropanamide
  参考文献：
  名称：

  将位阻二酰基化的1,2-苯二胺转化为2-取代的苯并咪唑。

  摘要：

  设计了一系列大体积的2-取代的苯并咪唑，以便为几个生物学靶标找到新的潜在客户。由它们的单酰化的对应物通过环脱水形成显示出强烈地依赖于酰基的性质。在二环己基甲基的情况下，仅在对称二酰基化前体的对甲苯磺酸/甲苯混合物中观察到环化。从混合二酰化衍生物开始分析机理。

  DOI：

  10.1248/cpb.53.492

文献信息

• Conversion of Sterically Hindered Diacylated 1,2-Phenylenediamines into 2-Substituted Benzimidazoles
  作者：Julie Charton、Sophie Girault-Mizzi、Christian Sergheraert

  DOI：10.1248/cpb.53.492

  日期：——

  for several biological targets. Formation by cyclodehydration from their monoacylated counterparts was shown to be strongly dependent upon the nature of the acyl group. In the case of a dicyclohexylmethyl group, cyclization was only observed in a p-toluenesulfonic acid/toluene mixture from the symmetrical diacylated precursor. Analysis of the mechanism was begun starting from mixed diacylated derivatives

  设计了一系列大体积的2-取代的苯并咪唑，以便为几个生物学靶标找到新的潜在客户。由它们的单酰化的对应物通过环脱水形成显示出强烈地依赖于酰基的性质。在二环己基甲基的情况下，仅在对称二酰基化前体的对甲苯磺酸/甲苯混合物中观察到环化。从混合二酰化衍生物开始分析机理。
• Enantioseparation of benzazoles and benzanilides on polysaccharide-based chiral columns
  作者：Takateru Kubota、Naotaka Sawada、Lili Zhou、Christopher J. Welch

  DOI：10.1002/chir.20732

  日期：2010.5.5

  The chiral recognition ability of the polysaccharide‐based chiral columns (Chiralpak AD‐RH, Chiralpak AS‐RJ, Chiralpak IC, Chiralcel OD‐RH, and Chiralcel OJ‐RH) for the benzazoles and the benzanilides was evaluated under reversed phase conditions. The columns showed the high chiral recognition ability for a wide range of benzazoles and benzanilides. Twenty‐one racemates were used for the evaluation

  在反相条件下评估了基于多糖的手性色谱柱（Chiralpak AD‐RH，Chiralpak AS‐RJ，Chiralpak IC，Chiralcel OD‐RH和Chiralcel OJ‐RH）的手性识别能力。色谱柱显示出对多种苯并恶唑和苯甲酰苯胺的高手性识别能力。使用21个外消旋体进行评估，并且在至少一根色谱柱上将20个外消旋体完全分离。尤其是AS-RH和OJ-RH对苯并唑具有较高的手性识别能力，而AD-RH，IC和OJ-RH对苯甲酰苯胺有效。手性2010。©2009 Wiley‐Liss，Inc.。
• Synthesis and biological evaluation of benzimidazole derivatives as potent AMP-activated protein kinase activators
  作者：Julie Charton、Sophie Girault-Mizzi、Marie-Ange Debreu-Fontaine、Fabienne Foufelle、Isabelle Hainault、Jean-Guy Bizot-Espiard、Daniel-Henri Caignard、Christian Sergheraert

  DOI：10.1016/j.bmc.2006.02.028

  日期：2006.7

  Design, synthesis and structure-activity relationships of beU:/AP/DTD501/BMC/4818nzimidazole derivatives as activators of the AMP-activated protein kinase (AMPK) are presented in this paper. AMPK is the central component of a protein kinase cascade that plays a key role in the regulation of energy balance. Once activated, AMPK initiates a series of responses that are aimed at restoring the energy balance of the cell and recent studies have indicated that AMPK plays an important role in regulation of the whole-body energy metabolism. The following study based on the lead compound S27847 involved modification of three regions of this compound. Preliminary structure activity relationships are being described. (c) 2006 Elsevier Ltd. All rights reserved.
• Discovery of Salermide-Related Sirtuin Inhibitors: Binding Mode Studies and Antiproliferative Effects in Cancer Cells Including Cancer Stem Cells
  作者：Dante Rotili、Domenico Tarantino、Angela Nebbioso、Chantal Paolini、Covadonga Huidobro、Ester Lara、Paolo Mellini、Alessia Lenoci、Riccardo Pezzi、Giorgia Botta、Maija Lahtela-Kakkonen、Antti Poso、Christian Steinkühler、Paola Gallinari、Ruggero De Maria、Mario Fraga、Manel Esteller、Lucia Altucci、Antonello Mai

  DOI：10.1021/jm3011614

  日期：2012.12.27

  Chemical changes performed on 1a (sirtinol) led to a series of SIRT1/2 inhibitors, in some cases more potent than la mainly against SIRT1. Tested in human leukemia U937 cells, the benzamide and anilide derivatives 1b, 1c, 2b, and 2c as well as the 4-(2-phenylpropyl)thioanalogue 4c showed huge apoptosis induction, while some sulfinyl and sulfonyl derivatives (5b, 5c, and 6a-c) were highly efficient in granulocytic differentiation. When assayed in human leukemia MOLT4 as well as in human breast MDA-MB-231 and colon RKO cancer cell lines, the anilide 2b (salermide) and the phenylpropylthio analogue 4b emerged as the most potent antiproliferative agents. Tested on colorectal carcinoma and glioblastoma multiforme cancer stem cells (CSCs) from patients, 2b was particularly potent against colorectal carcinoma CSCs, while 4b, 6a, and the SIRT2-selective inhibitor AGK-2 showed the highest effect against glioblastoma multiforme CSCs. Such compounds will be further explored for their broad-spectrum anticancer properties.