5-O-benzyl-2,3,6,7-tetradeoxy-L-threo-hept-6-enono-1,4-lactone | 1350649-48-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-O-benzyl-2,3,6,7-tetradeoxy-L-threo-hept-6-enono-1,4-lactone
• 英文别名: (5S)-5-[(1S)-1-phenylmethoxyprop-2-enyl]oxolan-2-one
• CAS: 1350649-48-7
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: NEVJHGJWEVRSBW-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-O-benzyl-2,3,6,7-tetradeoxy-L-threo-hept-6-enono-1,4-lactone 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 31.5h， 生成 (+)-muricatacin
  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：

  5-O-benzyl-2,3-dideoxy-D-xylo-heptono-1,4-lactone 在 咪唑 、 碘 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以96%的产率得到5-O-benzyl-2,3,6,7-tetradeoxy-L-threo-hept-6-enono-1,4-lactone
  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

文献信息

• Heteroannelated (+)-muricatacin mimics: synthesis, antiproliferative properties and structure–activity relationships
  作者：Bojana Srećo、Goran Benedeković、Mirjana Popsavin、Pavle Hadžić、Vesna Kojić、Gordana Bogdanović、Vladimir Divjaković、Velimir Popsavin

  DOI：10.1016/j.tet.2011.09.132

  日期：2011.12

  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.