(2S,3R,3aS,6aS)-2-benzyl-3-hydroxy-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-5-one | 1457973-57-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: (2S,3R,3aS,6aS)-2-benzyl-3-hydroxy-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-5-one
• CAS: 1457973-57-7
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: DTABFNPTFUDFKG-YRRQLQLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,6-anhydro-7-O-benzoyl-5-O-benzyl-2-deoxy-7-C-phenyl-D-glycero-L-ido-heptono-1,4-lactone 在 四氟化钛 作用下， 以 二氯甲烷 为溶剂， 反应 336.0h， 以42%的产率得到(1S,2R,11R,12R,16S)-2-phenyl-10,13,17-trioxatetracyclo[9.6.0.03,8.012,16]heptadeca-3,5,7-trien-14-one
  参考文献：
  名称：

  Heteroannelated and 7-deoxygenated goniofufurone mimics with antitumour activity: Design, synthesis and preliminary SAR studies

  摘要：

  Cytotoxic (+)-goniofufurone mimic such as benzoxepane 2 was preferentially formed after the treatment of 7-O-benzoyl-5-O-benzyl (+)-goniofufurone derivative 6 with titanium(IV) fluoride. However, the corresponding 7-epimer 5 (derivative of 7-epi-goniofufurone) under the similar reaction conditions gave mainly 7-deoxy derivative 7 as a result of an unexpected 1,5-hydride shift. Extension of this methodology to the enantiomer ent-6 provided cytotoxic (-)-goniofufurone mimics ent-2 and ent-7. Synthesized compounds showed diverse growth inhibitory effects against selected tumour cell lines, but were devoid of any significant toxicity towards the normal foetal lung fibroblasts (MRC-5). A SAR study reveals the structural features of these lactones that are beneficial for their antiproliferative activity, such as presence of an additional oxepane ring, the absolute stereochemistry and the presence of a deoxy function at the C-7 position. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.069

文献信息

• Heteroannelated and 7-deoxygenated goniofufurone mimics with antitumour activity: Design, synthesis and preliminary SAR studies
  作者：Velimir Popsavin、Jovana Francuz、Bojana Srećo Zelenović、Goran Benedeković、Mirjana Popsavin、Vesna Kojić、Gordana Bogdanović

  DOI：10.1016/j.bmcl.2013.08.069

  日期：2013.10

  Cytotoxic (+)-goniofufurone mimic such as benzoxepane 2 was preferentially formed after the treatment of 7-O-benzoyl-5-O-benzyl (+)-goniofufurone derivative 6 with titanium(IV) fluoride. However, the corresponding 7-epimer 5 (derivative of 7-epi-goniofufurone) under the similar reaction conditions gave mainly 7-deoxy derivative 7 as a result of an unexpected 1,5-hydride shift. Extension of this methodology to the enantiomer ent-6 provided cytotoxic (-)-goniofufurone mimics ent-2 and ent-7. Synthesized compounds showed diverse growth inhibitory effects against selected tumour cell lines, but were devoid of any significant toxicity towards the normal foetal lung fibroblasts (MRC-5). A SAR study reveals the structural features of these lactones that are beneficial for their antiproliferative activity, such as presence of an additional oxepane ring, the absolute stereochemistry and the presence of a deoxy function at the C-7 position. (C) 2013 Elsevier Ltd. All rights reserved.