(+)-(R)-(12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dien-1-yl benzoate | 220569-80-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+)-(R)-(12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dien-1-yl benzoate
• 英文别名: (R,12Z,15Z)-2-hydroxy-4-oxo-henicosa-12,15-dienyl benzoate；[(2R,12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dienyl] benzoate
• CAS: 220569-80-2
• 化学式: C₂₈H₄₂O₄
• 分子量: 442.639
• InChiKey: KWLCXZCGZVVJRD-IQZSKYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  32
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  亚油酸甲酯 在 N-[3,5-双(三氟甲基)苯基]-N'-[(8a,9S)-6'-甲氧基-9-金鸡宁]硫脲 、 吡啶 、 N,N-二异丙基乙胺 、 lithium chloride 、 lithium diisopropyl amide 、 苯硼酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 60.25h， 生成 (+)-(R)-(12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dien-1-yl benzoate 、 (R)-(12Z,15Z)-4-oxohenicosa-12,15-diene-1,2-diyl dibenzoate
  参考文献：
  名称：

  Synthesis and in vitro evaluation of analogues of avocado-produced toxin (+)-(R)-persin in human breast cancer cells

  摘要：

  A structure-activity study of several new synthetic analogues of the avocado-produced toxin persin has been conducted, with compounds being evaluated for their cytostatic and pro-apoptotic effects in human breast cancer cells. A 4-pyridinyl derivative demonstrated activity comparable to that of the natural product, suggesting future directions for exploration of structure-activity relationships. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.006

文献信息

• Synthesis and in vitro evaluation of analogues of avocado-produced toxin (+)-(R)-persin in human breast cancer cells
  作者：Darby G. Brooke、Elizabeth J. Shelley、Caroline G. Roberts、William A. Denny、Robert L. Sutherland、Alison J. Butt

  DOI：10.1016/j.bmc.2011.10.006

  日期：2011.12

  A structure-activity study of several new synthetic analogues of the avocado-produced toxin persin has been conducted, with compounds being evaluated for their cytostatic and pro-apoptotic effects in human breast cancer cells. A 4-pyridinyl derivative demonstrated activity comparable to that of the natural product, suggesting future directions for exploration of structure-activity relationships. (C) 2011 Elsevier Ltd. All rights reserved.