3,6-anhydro-5,7-di-O-benzyl-2-deoxy-D-ido-heptono-1,4-lactone | 279221-72-6

• 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: 3,6-anhydro-5,7-di-O-benzyl-2-deoxy-D-ido-heptono-1,4-lactone
• 英文别名: 3,6-anhydro-5,7-di-O-benzyl-2-deoxy-D-ido-heptono-2,4-lactone；3,6-anhydro-5,7-di-O-benzyl-2-deoxyidoheptono-1,4-lactone；(2R,3S,3aS,6aR)-3-phenylmethoxy-2-(phenylmethoxymethyl)-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-5-one
• CAS: 279221-72-6
• 化学式: C₂₁H₂₂O₅
• 分子量: 354.403
• InChiKey: CWIQCHQJGZMBSB-QCFAMHMHSA-N

物化性质

• 沸点：
  539.4±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,6-anhydro-5,7-di-O-benzyl-2-deoxy-D-ido-heptono-1,4-lactone 在 palladium on activated charcoal 氢气 作用下， 反应 24.0h， 以87%的产率得到3,6-anhydro-2-deoxy-D-ido-heptono-1,4-lactone
  参考文献：
  名称：

  与部分保护的糖乳糖醇衍生物的维蒂希反应。制备具有高细胞毒性的goniofufurone类似物

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2004.10.122
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 3,5-di-O-benzyl-D-xylofuranose 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以82%的产率得到3,6-anhydro-5,7-di-O-benzyl-2-deoxy-D-ido-heptono-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

• 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。
• Ring-Contraction vs Ring-Expansion Reactions of Spiro-cyclopropanecarboxylated Sugars
  作者：Bandi Ramakrishna、Perali Ramu Sridhar

  DOI：10.1021/ol402021e

  日期：2013.9.6

  Electrophilic ring opening of spiro-cyclopropanecarboxylated sugars followed by reaction with DBU revealed interesting ring-contraction and ring-expansion reactions depending on the substrate and the kind of hydroxyl protective group present adjacent to the Spiro center. A stereoselective method for accessing a new class of carbon chain extended keto-furanoses and C-glycosylated bicyclic compounds is reported.
• 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.
• 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。