(R)-(12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dien-1-yl isonicotinate | 1349697-89-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (R)-(12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dien-1-yl isonicotinate
• 英文别名: [(2R,12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dienyl] pyridine-4-carboxylate
• CAS: 1349697-89-7
• 化学式: C₂₇H₄₁NO₄
• 分子量: 443.627
• InChiKey: NJOSGDACXBKYLX-IPQYAGCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  32
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  76.5
• 氢给体数：
  1
• 氢受体数：
  5

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 、 2,4,6-三甲基吡啶 、 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 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 76.25h， 生成 (R)-(12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dien-1-yl isonicotinate
  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.