2,5-anhydro-4-azido-3,6-di-O-benzoyl-4-deoxy-D-gulose ethylene acetal | 228399-13-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-anhydro-4-azido-3,6-di-O-benzoyl-4-deoxy-D-gulose ethylene acetal
• 英文别名: [(2S,3S,4R,5R)-3-azido-4-benzoyloxy-5-(1,3-dioxolan-2-yl)oxolan-2-yl]methyl benzoate
• CAS: 228399-13-1
• 化学式: C₂₂H₂₁N₃O₇
• 分子量: 439.425
• InChiKey: XCDLLPZBPABAHG-FCGDIQPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  94.6
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-4-azido-3,6-di-O-benzoyl-4-deoxy-D-gulose ethylene acetal 在 吡啶 、 盐酸 、 palladium 10% on activated carbon 、 盐酸羟胺 、 氢气 、 sodium acetate 、 甲基磺酰氯 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 、 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 为溶剂， 反应 99.5h， 生成 ((2S,3S,4R,5S)-4-(benzoyloxy)-5-cyano-3-(2,2,2-trifluoroacetamido)tetrahydrofuran-2-yl)methyl benzoate
  参考文献：
  名称：

  在C-2'或C-3'位置具有氮功能的噻唑呋林立体异构体的基于结构的设计，合成和体外抗肿瘤活性。

  摘要：

  从d-葡萄糖开始，已设计并合成了三个具有d-阿拉伯立体化学和在C-2'位置（5-7）具有氮官能团的氮官能团的新的噻唑呋林类似物。已知的d-xylo立体异构体1（化合物2）以及两个在C-3'（3和4）带有氮官能团的新类似物也已由相同的糖前体合成。合成过程由以下三个阶段组成：（i）多步合成适当保护的戊呋喃糖基氰化物，（ii）通过将所得的呋喃呋喃糖基氰化物与l-半胱氨酸乙酯进行环缩合，然后再将其制得的呋喃呋喃糖基氰化物环化，来构建乙基噻唑-4-羧酸酯部分。脱氢，以及（iii）使用酯氨解将噻唑-4-甲酸乙酯最终转化为目标噻唑呋喃类似物。在基于细胞培养的测定中评估了噻唑呋林类似物的抗肿瘤活性。化合物3、4（d-xylo）和7（d-阿拉伯糖）显示出显着的抗肿瘤活性，IC50值在4-7 nM范围内。初步的结构-活性关系允许鉴定两个具有超过母体化合物1的抗增殖活性的类似物几个数量级（例如，抗Raji的比为

  DOI：

  10.1016/j.ejmech.2019.111712
• 作为产物：
  描述：

  2,5-anhydro-4,6-di-O-benzoyl-3-O-methanesulfonyl-D-glucose ethylene acetal 在 吡啶 、 sodium azide 、 calcium carbonate 作用下， 以 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 212.0h， 生成 2,5-anhydro-4-azido-3,6-di-O-benzoyl-4-deoxy-D-gulose ethylene acetal
  参考文献：
  名称：

  Synthesis and biological evaluation of new pyrazole- and tetrazole-related C-nucleosides with modified sugar moieties

  摘要：

  3(5)-Carboxamido-4-(beta-D-ribofuranosyl)pyrazoles bearing 2'-benzamido (15) and 3'-mesyloxy (29) isosteric groups, as well as the tetrazole C-nucleosides with 2-benzamido-2-deoxy-beta-D-ribofuranose (19) and 3-azido-3-deoxy-beta-D-xylofuranose (36) as sugar segments, have been synthesized starting from D-glucose, by utilizing the 2,5-anhydro-D-glucose ethylene acetal derivatives 1 and 20 as divergent intermediates. The C-nucleosides 15 and 36 were shown to be moderate inhibitors of the in vitro growth of both N2a and BHK 21 tumour cell lines, whereas 29 showed a selective, although not potent cytotoxic activity against N2a cells. Compound 29 also showed a moderate in vitro antiviral activity towards the rabies virus. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01126-7

文献信息

• De novo synthesis of two new cytotoxic tiazofurin analogues with modified sugar moieties
  作者：Mirjana Popsavin、Ljilja Torović、Vesna Kojić、Gordana Bogdanović、Saša Spaić、Velimir Popsavin

  DOI：10.1016/s0960-894x(03)00712-1

  日期：2003.10

  A divergent synthesis of two novel tiazofurin analogues, 2-(3-deoxy-3-fluoro-beta-D-xylofuranosyl)thiazole-4-carboxamide (2) and 2-(3-acetamido-3-deoxy-beta-D-xylofuranosyl)thiazole-4-carboxamide (3), has been achieved starting from D-glucose. Both nucleoside analogues were evaluated for their in vitro cytotoxicity against several human leukaemia and solid tumour cell lines.

  两种新型噻唑啉类似物2-（3-deoxy-3-fluoro-beta-D-xyfurfuranosyl）thiazole-4-caramide（2）和2-（3-acetamido-3-deoxy-beta-D-从D-葡萄糖开始已经获得了木呋喃糖基）噻唑-4-羧酰胺（3）。评估了两种核苷类似物对几种人类白血病和实体瘤细胞系的体外细胞毒性。
• 2-(3-Amino-3-deoxy-β-d-xylofuranosyl)thiazole-4-carboxamide: A new tiazofurin analogue with potent antitumour activity
  作者：Mirjana Popsavin、Saša Spaić、Miloš Svirčev、Vesna Kojić、Gordana Bogdanović、Velimir Popsavin

  DOI：10.1016/j.bmcl.2006.07.086

  日期：2006.10

  A new tiazofurin analogue, 2-(3-amino-3-deoxy-p-D-xylofuranosyl)thiazole-4-carboxamide (3), was synthesized starting from D-glucose and evaluated for its in vitro antiproliferative activity against a panel of human tumour cell lines. Compound 3 exhibited the most powerful cytotoxicity against K562 cells, being approximately 100-fold more potent than tiazofurin. This analogue was also active against Jurkat, HT-29 and HeLa malignant cells, with respective IC50 values being ca. 2-, 27- and 17-fold lower than those observed for tiazofurin. Remarkably, compound 3 did not exhibit any significant cytotoxicity towards normal foetal lung MRC-5 cell line. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of new pyrazole- and tetrazole-related C-nucleosides with modified sugar moieties
  作者：Mirjana Popsavin、Ljilja Torović、Saša Spaić、Srdjan Stankov、Agneš Kapor、Zoran Tomić、Velimir Popsavin

  DOI：10.1016/s0040-4020(01)01126-7

  日期：2002.1

  3(5)-Carboxamido-4-(beta-D-ribofuranosyl)pyrazoles bearing 2'-benzamido (15) and 3'-mesyloxy (29) isosteric groups, as well as the tetrazole C-nucleosides with 2-benzamido-2-deoxy-beta-D-ribofuranose (19) and 3-azido-3-deoxy-beta-D-xylofuranose (36) as sugar segments, have been synthesized starting from D-glucose, by utilizing the 2,5-anhydro-D-glucose ethylene acetal derivatives 1 and 20 as divergent intermediates. The C-nucleosides 15 and 36 were shown to be moderate inhibitors of the in vitro growth of both N2a and BHK 21 tumour cell lines, whereas 29 showed a selective, although not potent cytotoxic activity against N2a cells. Compound 29 also showed a moderate in vitro antiviral activity towards the rabies virus. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Structure based design, synthesis and in vitro antitumour activity of tiazofurin stereoisomers with nitrogen functions at the C-2′ or C-3′ positions
  作者：Vesna Kojić、Mirjana Popsavin、Saša Spaić、Dimitar Jakimov、Ivana Kovačević、Miloš Svirčev、Lidija Aleksić、Bojana Srećo Zelenović、Velimir Popsavin

  DOI：10.1016/j.ejmech.2019.111712

  日期：2019.12

  The tiazofurin analogues were evaluated for their antitumour activities in cell-culture-based assays. Compounds 3, 4 (d-xylo) and 7 (d-arabino), showed remarkable antitumour activities, with IC50 values in the range of 4-7 nM. Preliminary structure-activity relationship allowed identification of two analogues with antiproliferative activities exceeding that of the parent compound 1 for several orders

  从d-葡萄糖开始，已设计并合成了三个具有d-阿拉伯立体化学和在C-2'位置（5-7）具有氮官能团的氮官能团的新的噻唑呋林类似物。已知的d-xylo立体异构体1（化合物2）以及两个在C-3'（3和4）带有氮官能团的新类似物也已由相同的糖前体合成。合成过程由以下三个阶段组成：（i）多步合成适当保护的戊呋喃糖基氰化物，（ii）通过将所得的呋喃呋喃糖基氰化物与l-半胱氨酸乙酯进行环缩合，然后再将其制得的呋喃呋喃糖基氰化物环化，来构建乙基噻唑-4-羧酸酯部分。脱氢，以及（iii）使用酯氨解将噻唑-4-甲酸乙酯最终转化为目标噻唑呋喃类似物。在基于细胞培养的测定中评估了噻唑呋林类似物的抗肿瘤活性。化合物3、4（d-xylo）和7（d-阿拉伯糖）显示出显着的抗肿瘤活性，IC50值在4-7 nM范围内。初步的结构-活性关系允许鉴定两个具有超过母体化合物1的抗增殖活性的类似物几个数量级（例如，抗Raji的比为