(4S,6R,7S,8R)-7-hydroxy-6-hydroxymethyl-1,5-dioxa-2-oxobicyclo[3.3.0^4,8]octane

• 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: (4S,6R,7S,8R)-7-hydroxy-6-hydroxymethyl-1,5-dioxa-2-oxobicyclo[3.3.0^4,8]octane
• 英文别名: 3,6-anhydro-2-deoxy-D-galacto-heptono-1,4-lactone；(2R,3S,3aS,6aS)-3-hydroxy-2-(hydroxymethyl)-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-5-one
• 化学式: C₇H₁₀O₅
• 分子量: 174.153
• InChiKey: UNODOAJTNLUJEG-VYFZPWGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,5-di-O-benzyl-D-xylono-γ-lactone 在 palladium on activated charcoal 吡啶 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醚 、 乙酸乙酯 、 乙腈 为溶剂， 反应 37.63h， 生成 (4S,6R,7S,8R)-7-hydroxy-6-hydroxymethyl-1,5-dioxa-2-oxobicyclo[3.3.0^4,8]octane
  参考文献：
  名称：

  Synthesis and epimerisation studies on carbohydrate derived bicyclic tetronate esters: The synthesis of furanofurans related to the cytotoxic metabolite goniofufurone

  摘要：

  The synthesis of the D-xylo- 12, D-lyxo- 13, D-ribo- 14 and D-arabino-furanofurans 15 was accomplished from the readily available butyrolactones 4 and 5 via a non-classical Wittig cyclisation/hydrogenation sequence; these compounds are analogues of the cytotoxic natural product goniofufurone. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00164-6

文献信息

• Comprehensive Reinvestigation of The Reaction of D-Aldoses With Meldrum'S Acid Yielding Mainly Chain Extended 3,6-Anhydro-2-Deoxy-Aldono-1,4-Lactones
  作者：Peter Köll、Angelika Wernicke、József Kovács、Arne Lützen

  DOI：10.1080/07328300008544132

  日期：2000.1.1

  (butenolides) which in some cases could be isolated as by-products. Epimerisation at C-2 of the parent aldose occurred at least partially in most reactions. The products and their acetylated derivatives were characterized by 1H and 13C NMR spectroscopy. A proposed mechanism of this reaction is supported by additional experimental evidence.

  摘要在碱性条件下，所有非对映异构的醛基-D-戊糖和-D-己糖都与Meldrum的酸（2,2-二甲基-1,3-二恶烷-4,6-二酮）反应。最初由JA Galbis Perez等人报道的一种协议已被应用和优化。在1990年，在每种情况下，都发生了端基异构羟基被羧基-亚甲基正式取代，从而使母体醛糖的碳链延长了一个C2片段。产品主要是3,6-脱水-2-脱氧-醛基-1,4-内酯，其中内酯环被环化成呋喃类化合物。但是，D-甘露糖和D-lyxose也产生了吡喃类化合物3,7-脱水-1,4-内酯。中间体是不饱和的开链1，4-内酯（丁烯内酯），在某些情况下可以分离为副产物。在大多数反应中，母体醛糖在C-2处的差向异构化至少部分发生。产物及其乙酰化衍生物通过1 H和13 C NMR光谱表征。该反应的拟议机制得到了其他实验证据的支持。
• Wittig reaction with partially protected sugar lactol derivatives. Preparation of highly cytotoxic goniofufurone analogues
  作者：Velimir Popsavin、Sanja Grabež、Mirjana Popsavin、Ivana Krstić、Vesna Kojić、Gordana Bogdanović、Vladimir Divjaković

  DOI：10.1016/j.tetlet.2004.10.122

  日期：2004.12

  A new approach to the dephenyl goniofufurone analogue 2 and the corresponding (3S,4R)-stereoisomer 3 is reported. The resulting furanolactones 2 and 3 have shown a potent and selective in vitro cytotoxicity against certain human tumour cell lines.

  据报道，有一种新方法可用于脱苯古呋喃酮类似物2和相应的（3 S，4 R）-立体异构体3。所得的呋喃内酯2和3对某些人类肿瘤细胞系显示出有效的选择性体外细胞毒性。
• Synthesis and antiproliferative activity of simplified goniofufurone analogues
  作者：Bojana Sreco-Zelenovic、Sanja Grabez、Mirjana Popsavin、Vesna Kojic、Jovana Francuz、Velimir Popsavin

  DOI：10.2298/jsc200730056s

  日期：——

  Several (+)-goniofufurone analogues with simplified structures were designed, synthesized and evaluated for their in vitro antitumour activity, against a panel of human tumour cell lines. Dephenylated compounds 2 and 3 demonstrated remarkable antitumour activities, in the cultures of K562 and Raji cells with IC50 values in the range of 3.0?9.3 nM. Each of goniofufurone analogues lacking the tetrahydrofuran ring (4, 5 and 6) strongly inhibited the growth of at least one malignant cell line, with IC50 values in the range of 11-30 nM. Brief structure?activity relationship (SAR) analysis showed that the simplified goniofufurone analogues, designed by removing the phenyl group from C-7, or by opening the THF ring, could show stronger antiproliferative effects compared to control molecules. It is noticeable that analogues 2?8 are completely inactive with respect to the normal MRC-5 cell line. These findings, together with their potent antitumour activities, provide a suitable basis for the development of new and selective antitumour drugs.

  我们设计、合成了几种结构简化的 (+)-goniofufurone 类似物，并评估了它们对人类肿瘤细胞系的体外抗肿瘤活性。去苯基化合物 2 和 3 在 K562 和 Raji 细胞培养物中表现出显著的抗肿瘤活性，IC50 值在 3.0-9.3 nM 之间。缺少四氢呋喃环的每个贡碘呋喃酮类似物（4、5 和 6）都能强烈抑制至少一种恶性细胞系的生长，IC50 值在 11-30 nM 之间。简单的结构活性关系（SAR）分析表明，与对照分子相比，通过去除 C-7 上的苯基或打开四氢呋喃环而设计的简化贡碘呋喃酮类似物具有更强的抗增殖作用。值得注意的是，类似物 2?8 对正常的 MRC-5 细胞系完全无效。这些发现及其强大的抗肿瘤活性为开发新的选择性抗肿瘤药物提供了合适的基础。