1,2-O-cyclohexylidene-5-deoxy-5-C-dodecyl-α-D-xylo-pentofuranose | 1350649-55-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-cyclohexylidene-5-deoxy-5-C-dodecyl-α-D-xylo-pentofuranose
• CAS: 1350649-55-6
• 化学式: C₂₃H₄₂O₄
• 分子量: 382.584
• InChiKey: HUZNHSCLXXWLFC-CIAFKFPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.85
• 重原子数：
  27.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,2-O-cyclohexylidene-5-deoxy-5-C-dodecyl-α-D-xylo-pentofuranose 在 水 、 溶剂黄146 作用下， 反应 3.5h， 生成 5-deoxy-5-C-dodecyl-α-D-xylo-pentofuranose 、 5-deoxy-5-C-dodecyl-β-D-xylo-pentofuranose
  参考文献：
  名称：

  Heteroannelated (+)-muricatacin mimics: synthesis, antiproliferative properties and structure–activity relationships

  摘要：

  Six new (+)-muricatacin mimics bearing a furano-furanone core have been synthesized and their in vitro antiproliferative activity was evaluated against a panel of human tumour cell lines. A straightforward total synthesis of (+)-muricatacin (1) from D-xylose is disclosed providing a sample of 1 that served as a positive control in antitumour assays. All new compounds showed diverse antiproliferative effects against human malignant cell lines, but were devoid of any significant cytotoxicity towards the normal foetal lung fibroblasts (MRC-5). Additionally, the most of (+)-muricatacin analogues show selective cytotoxicities towards certain cancer cell lines, whereas only two of six analogues are broadly toxic against all cell lines under evaluation. A SAR study reveals the structural features that may be beneficial for the antiproliferative activity of these lactones. These include the absolute stereochemistry, introduction of a THF ring, interchange of the O-8 ether functionality and the C-8 methylene group in the side chain of muricatacin oxa analogues, as well as the one- or two-carbon homologation of the side chain in both 3 and 6. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.132
• 作为产物：
  描述：

  溴代十二烷 、 3,5-anhydro-1,2-O-cyclohexylidene-α-D-xylofuranose 在 碘 、 magnesium 、 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以56%的产率得到1,2-O-cyclohexylidene-5-deoxy-5-C-dodecyl-α-D-xylo-pentofuranose
  参考文献：
  名称：

  Heteroannelated (+)-muricatacin mimics: synthesis, antiproliferative properties and structure–activity relationships

  摘要：

  Six new (+)-muricatacin mimics bearing a furano-furanone core have been synthesized and their in vitro antiproliferative activity was evaluated against a panel of human tumour cell lines. A straightforward total synthesis of (+)-muricatacin (1) from D-xylose is disclosed providing a sample of 1 that served as a positive control in antitumour assays. All new compounds showed diverse antiproliferative effects against human malignant cell lines, but were devoid of any significant cytotoxicity towards the normal foetal lung fibroblasts (MRC-5). Additionally, the most of (+)-muricatacin analogues show selective cytotoxicities towards certain cancer cell lines, whereas only two of six analogues are broadly toxic against all cell lines under evaluation. A SAR study reveals the structural features that may be beneficial for the antiproliferative activity of these lactones. These include the absolute stereochemistry, introduction of a THF ring, interchange of the O-8 ether functionality and the C-8 methylene group in the side chain of muricatacin oxa analogues, as well as the one- or two-carbon homologation of the side chain in both 3 and 6. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.132