methyl (2R,4aR,9aR)-2-hydroxy-1,1,4a-trimethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthene-7-carboxylate | 1353178-18-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: methyl (2R,4aR,9aR)-2-hydroxy-1,1,4a-trimethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthene-7-carboxylate
• CAS: 1353178-18-3
• 化学式: C₁₈H₂₄O₄
• 分子量: 304.386
• InChiKey: UTPSNGVQUXSHKC-IIDMSEBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (2R,4aR,9aR)-2-hydroxy-1,1,4a-trimethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthene-7-carboxylate 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 15-冠醚-5 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 生成
  参考文献：
  名称：

  Relevance of the C-5 position to schweinfurthin induced cytotoxicity

  摘要：

  The schweinfurthins are an intriguing group of anti-proliferative agents that display low nanomolar activities against several cell types, including the human-derived glioblastoma cell line SF-295, but have little impact on other cell lines even at micromolar concentrations. This activity has inspired the synthesis of seven of the natural schweinfurthins, all with the correct absolute stereochemistry, and a variety of analogues designed to probe different facets of the pharmacophore. Reported herein is the synthesis of several new schweinfurthin analogues varied at the C-5 position along with data on their biological activity in the NCI 60 cell-line assay. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.034
• 作为产物：
  描述：

  在 三氟化硼乙醚 、 水 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到methyl (2R,4aR,9aR)-2-hydroxy-1,1,4a-trimethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthene-7-carboxylate
  参考文献：
  名称：

  Relevance of the C-5 position to schweinfurthin induced cytotoxicity

  摘要：

  The schweinfurthins are an intriguing group of anti-proliferative agents that display low nanomolar activities against several cell types, including the human-derived glioblastoma cell line SF-295, but have little impact on other cell lines even at micromolar concentrations. This activity has inspired the synthesis of seven of the natural schweinfurthins, all with the correct absolute stereochemistry, and a variety of analogues designed to probe different facets of the pharmacophore. Reported herein is the synthesis of several new schweinfurthin analogues varied at the C-5 position along with data on their biological activity in the NCI 60 cell-line assay. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.034

文献信息

• Efficient construction of ABC-tricyclic core of schweinfurthins and its application in amide based analog synthesis
  作者：Utpal Majumder、Xiaojie Zhu、Hong Du、Xiangyi Li、Guobin Miao、Maarten Postema、John Wang、Xingfeng Bao、Wanjun Zheng

  DOI：10.1016/j.tetlet.2024.155104

  日期：2024.6

  medicinal chemistry efforts, an efficient and reliable synthesis of amide isosteres of Schweinfurthin G, where the central olefinic linkage between C and D rings has been replaced with amide bond, is described. The approach relied on a copper mediated coupling reaction of organo-magnesium species with allylic chloride is easily amenable to rapid analoging to generate amide based isosteres of the natural

  为了加速药物化学工作，描述了 Schweinfurthin G 酰胺等排体的高效、可靠合成，其中 C 和 D 环之间的中心烯键已被酰胺键取代。该方法依赖于有机镁物质与烯丙基氯的铜介导的偶联反应，易于快速模拟以生成基于酰胺的天然产物等排物。