santamarine

• 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: santamarine
• 英文别名: santamarin；(3aS,5aR,6R,9bS)-6-hydroxy-5a,9-dimethyl-3-methylidene-4,5,6,7,9a,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: PLSSEPIRACGCBO-MHWJQKJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  santamarine 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以43%的产率得到11,13-dehydroanhydrojudaicin
  参考文献：
  名称：

  Facile synthesis of anhydrojudaicin and 11,13-dehydroanhydrojudaicin, two eudesmanolide-skeleton lactones with potential allelopathic activity

  摘要：

  Natural product anhydrojudaicin (7) is a eudesmanolide that has been synthesized from costunolide (1) in three steps with good yield, simplifying procedures available in the literature. The key step was the efficient oxidation and rearrangement using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). Following the same methodology, 11,13-dehydroanhydrojudaicin (8) was prepared for the first time. All compounds were characterized and tested in three specific bioassays: phytotoxicity bioassays on wheat coleoptile and on weed seeds (Amaranthus viridis, Echinochloa crus-galli and Panicum maximum); as well as bioassay of germination of parasitic weed seeds of broomrape (Orobanchaceae). The final products showed better activity profiles than the starting eudesmanolide in all bioassays. The data allow us to propose compounds 7 and 8 as leads for new natural product-based agrochemicals.

  DOI：

  10.1016/j.phytol.2019.04.014
• 作为产物：
  描述：

  木香烃内酯 在 silica gel 、 间氯过氧苯甲酸 作用下， 以 正己烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 reynosin 、 santamarine 、 1β-hydroxy-5α,6β,7αH-eudesma-4(5),11(13)-dien-12,6-olide
  参考文献：
  名称：

  Facile synthesis of anhydrojudaicin and 11,13-dehydroanhydrojudaicin, two eudesmanolide-skeleton lactones with potential allelopathic activity

  摘要：

  Natural product anhydrojudaicin (7) is a eudesmanolide that has been synthesized from costunolide (1) in three steps with good yield, simplifying procedures available in the literature. The key step was the efficient oxidation and rearrangement using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). Following the same methodology, 11,13-dehydroanhydrojudaicin (8) was prepared for the first time. All compounds were characterized and tested in three specific bioassays: phytotoxicity bioassays on wheat coleoptile and on weed seeds (Amaranthus viridis, Echinochloa crus-galli and Panicum maximum); as well as bioassay of germination of parasitic weed seeds of broomrape (Orobanchaceae). The final products showed better activity profiles than the starting eudesmanolide in all bioassays. The data allow us to propose compounds 7 and 8 as leads for new natural product-based agrochemicals.

  DOI：

  10.1016/j.phytol.2019.04.014

文献信息

• Synthesis and Cytotoxic Activity of the Products of Addition of Thiophenol to Sesquiterpene Lactones
  作者：A. V. Semakov、L. V. Anikina、S. G. Klochkov

  DOI：10.1134/s106816202104018x

  日期：2021.7

  sesquiterpene lactones modified at the lactone ring with a thiophenol residue have been synthesized. The resulting conjugates with thiophenol have capacity for the oxidation–elimination reaction by the action of ROS of a tumor cell with the release of initial cytotoxic lactones. It has been proposed to use the resulting sulfur-containing conjugates as ROS-activated prodrugs of sesquiterpene lactones. The antiproliferative

  摘要—— 已经合成了在内酯环上用苯硫酚残基修饰的倍半萜内酯衍生物。由此产生的与苯硫酚的结合物具有通过肿瘤细胞的 ROS 的作用与初始细胞毒性内酯的释放进行氧化消除反应的能力。已提议将所得含硫缀合物用作倍半萜内酯的 ROS 活化前药。已在肿瘤和假性正常细胞系上检查了缀合物的抗增殖特性。偶联物的细胞毒性低于母体内酯；然而，在某些情况下，如阿兰内酯与青蒿素的结合物，它在所有测试的肿瘤细胞系中保持中等。
• Facile synthesis of anhydrojudaicin and 11,13-dehydroanhydrojudaicin, two eudesmanolide-skeleton lactones with potential allelopathic activity
  作者：Jesús G. Zorrilla、Carlos Rial、Rosa M. Varela、José M.G. Molinillo、Francisco A. Macías

  DOI：10.1016/j.phytol.2019.04.014

  日期：2019.6

  Natural product anhydrojudaicin (7) is a eudesmanolide that has been synthesized from costunolide (1) in three steps with good yield, simplifying procedures available in the literature. The key step was the efficient oxidation and rearrangement using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). Following the same methodology, 11,13-dehydroanhydrojudaicin (8) was prepared for the first time. All compounds were characterized and tested in three specific bioassays: phytotoxicity bioassays on wheat coleoptile and on weed seeds (Amaranthus viridis, Echinochloa crus-galli and Panicum maximum); as well as bioassay of germination of parasitic weed seeds of broomrape (Orobanchaceae). The final products showed better activity profiles than the starting eudesmanolide in all bioassays. The data allow us to propose compounds 7 and 8 as leads for new natural product-based agrochemicals.