3,5-di-O-benzoyl-1,2-O-{(1R)-1-[4-(ethoxycarbonyl)-1,3-thiazol-2-yl]ethylidene}-α-D-xylofuranose | 1409941-24-7

• 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: 3,5-di-O-benzoyl-1,2-O-{(1R)-1-[4-(ethoxycarbonyl)-1,3-thiazol-2-yl]ethylidene}-α-D-xylofuranose
• 英文别名: ethyl 2-[(2R,3aR,5R,6S,6aR)-6-benzoyloxy-5-(benzoyloxymethyl)-2-methyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-2-yl]-1,3-thiazole-4-carboxylate
• CAS: 1409941-24-7
• 化学式: C₂₇H₂₅NO₉S
• 分子量: 539.563
• InChiKey: JFIRIEPTMHJODA-HQKUHQLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  148
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3,5-di-O-benzoyl-1,2-O-{(1R)-1-[4-(ethoxycarbonyl)-1,3-thiazol-2-yl]ethylidene}-α-D-xylofuranose 在 氨 作用下， 以 甲醇 为溶剂， 反应 144.0h， 以90%的产率得到1,2-O-[(1R)-1-(4-carbamoyl-1,3-thiazol-2-yl)ethylidene]-α-D-xylofuranose
  参考文献：
  名称：

  合成并体外抗肿瘤筛选2-（β-d-xylofuranosyl）thiaazole-4-carboxamide和两个新颖的噻唑呋喃类似物，其取代的四氢呋喃二恶唑部分为糖模拟物

  摘要：

  2-（β- d - xylofuranosyl）thiaazole -4-carboxamide（2）和两个新的噻唑呋林类似物与5-羟甲基-2-甲基-四氢呋喃[2,3- d ] [1,3] dioxol-6-已经合成了作为糖模拟物的O1部分（27和28），并评估了它们对一组人类肿瘤细胞系（K562，HL 60，Jurkat，Raji和HeLa）的体外抗肿瘤活性。与以前的文献报道相反，代谢MTT测定显示出对K562（IC 50  = 0.15μM）和HL-60（IC 50  = 0.13μM）细胞的显着细胞毒性为2。流式细胞仪数据表明类似物2的细胞毒性作用与噻唑呋林相反，K562细胞培养物中的K562细胞凋亡可能是由细胞凋亡介导的，而噻唑呋林在24 h后不诱导K562细胞凋亡，因此提示了不同的作用机制。所有三种类似物2，27和28也对Jurkat，Raji和HeLa细胞活性，用IC 50倍在从0

  DOI：

  10.1016/j.bmcl.2012.08.093
• 作为产物：
  描述：

  1,2-di-O-acetyl-3,5-di-O-benzoyl-D-xylofuranose 在 三氯溴甲烷 、 三甲基氰硅烷 、 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 28.5h， 生成 3,5-di-O-benzoyl-1,2-O-{(1R)-1-[4-(ethoxycarbonyl)-1,3-thiazol-2-yl]ethylidene}-α-D-xylofuranose
  参考文献：
  名称：

  2-Substituted thiazole-4-carboxamide derivatives as tiazofurin mimics: synthesis and in vitro antitumour activity

  摘要：

  Tiazofurin analogues bearing a 5-hydroxymethy1-2-methyl-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol moiety as a sugar mimic (2 and 3), and two novel thiazole-based acyclo-C-nucleosides 4 and 16 have been synthesized in multistep sequences starting from D-xylose (compounds 2 and 3) or from D-arabinose (compounds 4 and 16). All synthesized analogues showed potent in vitro antitumour activities against a panel of human tumour cell lines. Flow cytometry data suggest that cytotoxic effects of analogues 2-4 and 16 in the culture of 1(562 cells might be mediated by apoptosis. It was also found that these analogues induced changes in cell cycle distribution of 1(562 cells. Results of western blot analysis (upregulation of Bax and downregulation of Bc1-2, activation of caspase-3 and the presence of a PARP cleavage product) suggest that tiazofurin mimics (2-4 and 16) in 1(562 cells induced apoptosis in a caspasedependent way. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.02.035

文献信息

• Synthesis and in vitro antitumour screening of 2-(β-d-xylofuranosyl)thiazole-4-carboxamide and two novel tiazofurin analogues with substituted tetrahydrofurodioxol moiety as a sugar mimic
  作者：Mirjana Popsavin、Saša Spaić、Miloš Svirčev、Vesna Kojić、Gordana Bogdanović、Velimir Popsavin

  DOI：10.1016/j.bmcl.2012.08.093

  日期：2012.11

  2-(β-d-xylofuranosyl)thiazole-4-carboxamide (2) and two new tiazofurin analogues with 5-hydroxymethyl-2-methyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol moiety as a sugar mimic (27 and 28) have been synthesized and evaluated for their in vitro antitumour activity against a panel of human tumour cell lines (K562, HL 60, Jurkat, Raji and HeLa). In contrast to previous literature reports, a metabolic MTT

  2-（β- d - xylofuranosyl）thiaazole -4-carboxamide（2）和两个新的噻唑呋林类似物与5-羟甲基-2-甲基-四氢呋喃[2,3- d ] [1,3] dioxol-6-已经合成了作为糖模拟物的O1部分（27和28），并评估了它们对一组人类肿瘤细胞系（K562，HL 60，Jurkat，Raji和HeLa）的体外抗肿瘤活性。与以前的文献报道相反，代谢MTT测定显示出对K562（IC 50  = 0.15μM）和HL-60（IC 50  = 0.13μM）细胞的显着细胞毒性为2。流式细胞仪数据表明类似物2的细胞毒性作用与噻唑呋林相反，K562细胞培养物中的K562细胞凋亡可能是由细胞凋亡介导的，而噻唑呋林在24 h后不诱导K562细胞凋亡，因此提示了不同的作用机制。所有三种类似物2，27和28也对Jurkat，Raji和HeLa细胞活性，用IC 50倍在从0
• 2-Substituted thiazole-4-carboxamide derivatives as tiazofurin mimics: synthesis and in vitro antitumour activity
  作者：Mirjana Popsavin、Vesna Kojić、Saša Spaić、Miloš Svirčev、Gordana Bogdanović、Dimitar Jakimov、Lidija Aleksić、Velimir Popsavin

  DOI：10.1016/j.tet.2014.02.035

  日期：2014.4

  Tiazofurin analogues bearing a 5-hydroxymethy1-2-methyl-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol moiety as a sugar mimic (2 and 3), and two novel thiazole-based acyclo-C-nucleosides 4 and 16 have been synthesized in multistep sequences starting from D-xylose (compounds 2 and 3) or from D-arabinose (compounds 4 and 16). All synthesized analogues showed potent in vitro antitumour activities against a panel of human tumour cell lines. Flow cytometry data suggest that cytotoxic effects of analogues 2-4 and 16 in the culture of 1(562 cells might be mediated by apoptosis. It was also found that these analogues induced changes in cell cycle distribution of 1(562 cells. Results of western blot analysis (upregulation of Bax and downregulation of Bc1-2, activation of caspase-3 and the presence of a PARP cleavage product) suggest that tiazofurin mimics (2-4 and 16) in 1(562 cells induced apoptosis in a caspasedependent way. (C) 2014 Elsevier Ltd. All rights reserved.