N-(2-hydroxy-4-nitrophenyl)-retinamide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-(2-hydroxy-4-nitrophenyl)-retinamide
• 英文别名: (2E,4E,6E,8E)-N-(2-hydroxy-4-nitrophenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide
• 化学式: C₂₆H₃₂N₂O₄
• 分子量: 436.551
• InChiKey: QQVXAQAVLCWILE-HPWKXKAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  维A酸 在 吡啶 、 六氯丙酮 、 triphenylphosphine-resin 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 N-(2-hydroxy-4-nitrophenyl)-retinamide
  参考文献：
  名称：

  Solid phase-assisted synthesis and screening of a small library of N-(4-hydroxyphenyl)retinamide (4-HPR) analogs

  摘要：

  Using solid phase-assisted synthesis and purification, a 49 member library of analogs of the main mammary tumor chemopreventive retinoid N-(4-hydroxyphenyl)retinamide (4-HPR) has been prepared. After prescreening for growth inhibitory activity in human mammary tumor cells (MCF-7) in culture, most of those analogs which showed activity (12 of them) were assayed for apoptosis-inducing activity in the MCF-7 cells. At least 3 of the analogs (13, 24, and 28) showed activity approaching that of 4-HPR. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.050

文献信息

• Solid phase synthesis of arylretinamides
  申请人：——

  公开号：US20030105164A1

  公开（公告）日：2003-06-05

  A solid phase synthetic method for preparing arylretinamides is provided. The method comprises reacting hexachloroacetone with a solvent-suspended resin-bound triphenylphosphine to provide a suspension comprising an activated chlorinating reagent; reacting retinoic acid with the activated chlorinating reagent to provide retinoyl chloride; adding pyridine and a select arylamine to the resulting mixture; and stirring the resulting mixture for a time and at a temperature sufficient for the select arylamine to react with the retinoyl chloride and provide the arylretinamide. Also provided, are select arylretinamides that can be prepared by the present method, and methods of using such arylretinamides to induce apoptosis in cancer cells.

  提供了一种用于制备芳基维甲酰胺的固相合成方法。该方法包括将六氯乙酮与悬浮于溶剂中的树脂结合的三苯基膦反应，以提供含有活化氯化试剂的悬浮液；将维甲酸与活化氯化试剂反应以提供维甲酰氯；向得到的混合物中加入吡啶和选择的芳基胺；并在足够时间和温度下搅拌得到的混合物，以使选择的芳基胺与维甲酰氯反应并提供芳基维甲酰胺。还提供了可以通过该方法制备的选择性芳基维甲酰胺，以及使用这些芳基维甲酰胺在癌细胞中诱导凋亡的方法。
• US6696606B2
  申请人：——

  公开号：US6696606B2

  公开（公告）日：2004-02-24
• US7550510B2
  申请人：——

  公开号：US7550510B2

  公开（公告）日：2009-06-23
• Solid phase-assisted synthesis and screening of a small library of N-(4-hydroxyphenyl)retinamide (4-HPR) analogs
  作者：Serena M. Mershon、Allyson L. Anding、Jason S. Chapman、Margaret Clagett-Dame、Laura A. Stonerock、Robert W. Curley

  DOI：10.1016/j.bmcl.2006.10.050

  日期：2007.2

  Using solid phase-assisted synthesis and purification, a 49 member library of analogs of the main mammary tumor chemopreventive retinoid N-(4-hydroxyphenyl)retinamide (4-HPR) has been prepared. After prescreening for growth inhibitory activity in human mammary tumor cells (MCF-7) in culture, most of those analogs which showed activity (12 of them) were assayed for apoptosis-inducing activity in the MCF-7 cells. At least 3 of the analogs (13, 24, and 28) showed activity approaching that of 4-HPR. (c) 2006 Elsevier Ltd. All rights reserved.