Xanthone disulfate | 1316308-39-0

• 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: Xanthone disulfate
• 英文别名: xanthone-3,6-O,O-bis(sulfate)；(9-Oxo-6-sulfooxyxanthen-3-yl) hydrogen sulfate
• CAS: 1316308-39-0
• 化学式: C₁₃H₈O₁₀S₂
• 分子量: 388.333
• InChiKey: SNXUDJGWJWHUKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  170
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2,2',4,4'-四羟基二苯甲酮 在 sulfur trioxide pyridine complex 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 生成 Xanthone disulfate
  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

• Synthesis of Xanthones and Benzophenones as Inhibitors of Tumor Cell Growth
  作者：Elisangela Costa、Emilia Sousa、Nair Nazareth、Maria S.J. Nascimento、Madalena M.M. Pinto

  DOI：10.2174/157018010791526250

  日期：2010.8.1

  The synthesis of two new sulfated xanthones and two O-substituted benzophenones was carried out to evaluate for their inhibitory effect on growth of human tumor cell lines. The sulfation of 3,6-(2) and 3,4-dihydroxyxanthone (3) was accomplished using sulfur trioxide-pyridine to give, respectively, xanthone-3,6-O,O-bis(sulfate) (4) and xanthone- 3,4-O,O-bis(sulfate) (5). Treatment of 2,2,4,4-tetrahydroxybenzophenone (6) with acetic acid and prenyl bromide furnished 2,2,4,4- tetraacetoxybenzophenone (7) and (5-hydroxy-2,2-dimethylchroman-6-yl)(2-hydroxy-4-(tertpentyloxy) phenyl)methanone (8), respectively. Compounds 2-8 were tested for their effect on the in vitro growth of four representative human tumor cell lines: MCF-7 ER(+) (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer), SF-268 (glioma), and A375-C5 (melanoma). Compounds 2 and 7-8 showed an inhibitory activity in the μM range.`

  对两种新的硫酸化氧杂蒽酮和两种O-取代二苯甲酮进行了合成，以评估它们对人类肿瘤细胞系生长的抑制作用。使用三氧化硫-吡啶对3,6-(2)和3,4-二羟基氧杂蒽酮（3）进行硫酸化，分别得到氧杂蒽酮-3,6-O,O-双（硫酸盐）（4）和氧杂蒽酮-3,4-O,O-双（硫酸盐）（5）。用乙酸和异戊烯基溴化物处理2,2,4,4-四羟基二苯甲酮（6），分别得到2,2,4,4-四乙酰氧基二苯甲酮（7）和（5-羟基-2,2-二甲基苯并二氢吡喃-6-基）（2-羟基-4-（叔戊基氧基）苯基）甲酮（8）。对化合物2-8在体外对四种典型人类肿瘤细胞系生长的抑制作用进行了测试：MCF-7 ER(+)（乳腺癌腺癌）、NCI-H460（非小细胞肺癌）、SF-268（胶质瘤）和A375-C5（黑色素瘤）。化合物2和
• 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.