mangiferin 2',3,3',4',6,6',7-O-heptasulfate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: mangiferin 2',3,3',4',6,6',7-O-heptasulfate
• 英文别名: Mangiferin heptasulfate；[1-hydroxy-9-oxo-6,7-disulfooxy-2-[(2S,3S,4R,5R,6R)-3,4,5-trisulfooxy-6-(sulfooxymethyl)oxan-2-yl]xanthen-3-yl] hydrogen sulfate
• 化学式: C₁₉H₁₈O₃₂S₇
• 分子量: 982.795
• InChiKey: ZAYZYKTZYDABSH-PXHCZXJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  58
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  560
• 氢给体数：
  8
• 氢受体数：
  32

反应信息

• 作为反应物：
  描述：

  mangiferin 2',3,3',4',6,6',7-O-heptasulfate 在 sodium acetate 作用下， 以 乙醚 、 水 、 丙酮 为溶剂， 以1.04 g的产率得到
  参考文献：
  名称：

  Polysulfated Xanthones: Multipathway Development of a New Generation of Dual Anticoagulant/Antiplatelet Agents

  摘要：

  A multipathway strategy was used to evaluate the in vitro and in vivo antithrombotic effects of a new synthetic family of sulfated small molecules. Polysulfated xanthonosides showed highly effective anticoagulation effects in vitro, both in plasma (dotting times) and in whole human blood (thromboelastography), as well as in vivo (ip administration, mice). Physicochemical properties were assessed for mangiferin heptasulfate (7), which showed high solubility and stability in water and in human plasma and no putative hepatotoxicity in vivo. Mangiferin heptasulfate (7) was found to be a direct inhibitor of FXa, while persulfated 3,6-(O-beta-glucopyranosyl)xanthone (13) acted as a dual inhibitor of FXa (directly and by antithrombin III activation). By impedance aggregometry, compounds 7 and 13 exhibited the antiplatelet effect by inhibition of both arachidonic acid and ADP-induced platelet aggregation. Dual anticoagulant/antiplatelet agents, such as sulfated xanthonosides 7 and 13, are expected to lead to a new therapeutic approach for the treatment of both venous and arterial thrombosis.

  DOI：

  10.1021/jm2006589
• 作为产物：
  描述：

  芒果苷 在 三氧化硫-三乙胺复合物 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 生成 mangiferin 2',3,3',4',6,6',7-O-heptasulfate
  参考文献：
  名称：

  Polysulfated Xanthones: Multipathway Development of a New Generation of Dual Anticoagulant/Antiplatelet Agents

  摘要：

  A multipathway strategy was used to evaluate the in vitro and in vivo antithrombotic effects of a new synthetic family of sulfated small molecules. Polysulfated xanthonosides showed highly effective anticoagulation effects in vitro, both in plasma (dotting times) and in whole human blood (thromboelastography), as well as in vivo (ip administration, mice). Physicochemical properties were assessed for mangiferin heptasulfate (7), which showed high solubility and stability in water and in human plasma and no putative hepatotoxicity in vivo. Mangiferin heptasulfate (7) was found to be a direct inhibitor of FXa, while persulfated 3,6-(O-beta-glucopyranosyl)xanthone (13) acted as a dual inhibitor of FXa (directly and by antithrombin III activation). By impedance aggregometry, compounds 7 and 13 exhibited the antiplatelet effect by inhibition of both arachidonic acid and ADP-induced platelet aggregation. Dual anticoagulant/antiplatelet agents, such as sulfated xanthonosides 7 and 13, are expected to lead to a new therapeutic approach for the treatment of both venous and arterial thrombosis.

  DOI：

  10.1021/jm2006589

文献信息

• Polysulfated Xanthones: Multipathway Development of a New Generation of Dual Anticoagulant/Antiplatelet Agents
  作者：Marta Correia-da-Silva、Emília Sousa、Bárbara Duarte、Franklim Marques、Félix Carvalho、Luís M. Cunha-Ribeiro、Madalena M. M. Pinto

  DOI：10.1021/jm2006589

  日期：2011.8.11

  A multipathway strategy was used to evaluate the in vitro and in vivo antithrombotic effects of a new synthetic family of sulfated small molecules. Polysulfated xanthonosides showed highly effective anticoagulation effects in vitro, both in plasma (dotting times) and in whole human blood (thromboelastography), as well as in vivo (ip administration, mice). Physicochemical properties were assessed for mangiferin heptasulfate (7), which showed high solubility and stability in water and in human plasma and no putative hepatotoxicity in vivo. Mangiferin heptasulfate (7) was found to be a direct inhibitor of FXa, while persulfated 3,6-(O-beta-glucopyranosyl)xanthone (13) acted as a dual inhibitor of FXa (directly and by antithrombin III activation). By impedance aggregometry, compounds 7 and 13 exhibited the antiplatelet effect by inhibition of both arachidonic acid and ADP-induced platelet aggregation. Dual anticoagulant/antiplatelet agents, such as sulfated xanthonosides 7 and 13, are expected to lead to a new therapeutic approach for the treatment of both venous and arterial thrombosis.