methyl (Z)-20-hydroxy-3,4-bis(methoxycarbonyl)-3-eicosadienoate | 181514-08-9

• 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: methyl (Z)-20-hydroxy-3,4-bis(methoxycarbonyl)-3-eicosadienoate
• 英文别名: trimethyl (E)-19-hydroxynonadec-2-ene-1,2,3-tricarboxylate
• CAS: 181514-08-9
• 化学式: C₂₅H₄₄O₇
• 分子量: 456.62
• InChiKey: ZONQTZLQYBRRRL-QURGRASLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  32
• 可旋转键数：
  23
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (Z)-20-hydroxy-3,4-bis(methoxycarbonyl)-3-eicosadienoate 在 lithium hydroxide 作用下， 以 丙酮 为溶剂， 以1 mg的产率得到(E)-3-Carboxy-2-(16-hydroxy-hexadecyl)-pent-2-enedioic acid
  参考文献：
  名称：

  Oreganic acid: a potent novel inhibitor of ras farnesyl-protein transferase from an endophytic fungus

  摘要：

  Inhibitors of farnesyl-protein transferase (FPTase) have the potential of being anticancer agents for tumors in which ras is found mutated and contributes to cell transformation. From the screening of the extracts tricarboxylated alkylsulfate, oreganic acid (1), as a potent (IC50 = 14 nM) and specific inhibitor of FPTase. Its desulfated analog (4) was less active (IC50 = 3.3 mu M). The trimethylester (2) and its desulfated analog (3) were inactive. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00372-1
• 作为产物：
  描述：

  methyl (E)-3,4-bis(methoxycarbonyl)-20-sulfooxy-3-eicosenoate 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以3.4 mg的产率得到methyl (Z)-20-hydroxy-3,4-bis(methoxycarbonyl)-3-eicosadienoate
  参考文献：
  名称：

  Oreganic acid: a potent novel inhibitor of ras farnesyl-protein transferase from an endophytic fungus

  摘要：

  Inhibitors of farnesyl-protein transferase (FPTase) have the potential of being anticancer agents for tumors in which ras is found mutated and contributes to cell transformation. From the screening of the extracts tricarboxylated alkylsulfate, oreganic acid (1), as a potent (IC50 = 14 nM) and specific inhibitor of FPTase. Its desulfated analog (4) was less active (IC50 = 3.3 mu M). The trimethylester (2) and its desulfated analog (3) were inactive. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00372-1

文献信息

• METHOD FOR PREPARING OREGANIC ACID
  申请人：Noheda Marín Pedro

  公开号：US20110301370A1

  公开（公告）日：2011-12-08

  The present invention is aimed at a process for obtaining oreganic acid and derivatives thereof, to the intermediate compounds of this synthesis and to the use of

  本发明旨在提供一种获得有机酸及其衍生物的方法，以及该合成的中间化合物和其用途。
• EP2287146
  申请人：——

  公开号：——

  公开（公告）日：——
• Oreganic acid: a potent novel inhibitor of ras farnesyl-protein transferase from an endophytic fungus
  作者：Hiranthi Jayasuriya、Gerald F. Bills、Carmen Cascales、Deborah L. Zink、Michael A. Goetz、Rosalind G. Jenkins、Keith C. Silverman、Russell B. Lingham、Sheo B. Singh

  DOI：10.1016/0960-894x(96)00372-1

  日期：1996.9

  Inhibitors of farnesyl-protein transferase (FPTase) have the potential of being anticancer agents for tumors in which ras is found mutated and contributes to cell transformation. From the screening of the extracts tricarboxylated alkylsulfate, oreganic acid (1), as a potent (IC50 = 14 nM) and specific inhibitor of FPTase. Its desulfated analog (4) was less active (IC50 = 3.3 mu M). The trimethylester (2) and its desulfated analog (3) were inactive. Copyright (C) 1996 Elsevier Science Ltd