3-(3-bromopropoxy)xanthone | 153336-97-1

• 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: 3-(3-bromopropoxy)xanthone
• CAS: 153336-97-1
• 化学式: C₁₆H₁₃BrO₃
• 分子量: 333.181
• InChiKey: SWWCSGASTVNKCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  39.44
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  哌嗪 、 3-(3-bromopropoxy)xanthone 以 乙醇 为溶剂， 反应 6.0h， 以38%的产率得到3-[3-(piperazino)-propoxy]xanthone
  参考文献：
  名称：

  Antioxidant xanthone derivatives induce cell cycle arrest and apoptosis and enhance cell death induced by cisplatin in NTUB1 cells associated with ROS

  摘要：

  In an effort to develop novel antioxidant as anticancer agents, a series of xanthones were prepared. In vitro screening, the synthetic xanthones revealed significant inhibitory effects on xanthine oxidase and ABTS radical-cation scavenging activity. The selective compounds 2 and 8 induced an accumulation of NTUB1 cells in the G(1) phase arrest and cellular apoptosis by the increase of ROS level. The combination of cisplatin and 2 significantly enhanced the cell death in NTUB1 cells. Compounds 2 and 8 did not show cytotoxic activity in selected concentrations against SV-HUC1 cells. The present results suggested that antioxidants 2 and 8 may be used as anticancer agent for enhancing the therapeutic efficacy of anticancer agents and to reduce their side effect. (c) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.043
• 作为产物：
  描述：

  甲氧基苯甲酰氯 在 吡啶 、 aluminum (III) chloride 、 四甲基氢氧化铵 、 氢碘酸 、 sodium hydroxide 、 苯酚 作用下， 以 乙醚 、 水 、 正丁醇 为溶剂， 反应 57.0h， 生成 3-(3-bromopropoxy)xanthone
  参考文献：
  名称：

  Antioxidant xanthone derivatives induce cell cycle arrest and apoptosis and enhance cell death induced by cisplatin in NTUB1 cells associated with ROS

  摘要：

  In an effort to develop novel antioxidant as anticancer agents, a series of xanthones were prepared. In vitro screening, the synthetic xanthones revealed significant inhibitory effects on xanthine oxidase and ABTS radical-cation scavenging activity. The selective compounds 2 and 8 induced an accumulation of NTUB1 cells in the G(1) phase arrest and cellular apoptosis by the increase of ROS level. The combination of cisplatin and 2 significantly enhanced the cell death in NTUB1 cells. Compounds 2 and 8 did not show cytotoxic activity in selected concentrations against SV-HUC1 cells. The present results suggested that antioxidants 2 and 8 may be used as anticancer agent for enhancing the therapeutic efficacy of anticancer agents and to reduce their side effect. (c) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.043

文献信息

• γ-Pyrone Compounds. 5. Synthesis and Antiplatelet Effects of Xanthonoxypropanolamines and Related Compounds
  作者：Shorong-Shii Liou、Chun-Nan Lin、Che-Ming Teng、Feng-Nien Ko

  DOI：10.1002/jps.2600830325

  日期：1994.3

  A series of simple xanthonoxypropanolamines and related compounds were synthesized. 3-[3-(Cyclopropylamino)propoxy]-xanthone showed same potent antiplatelet effects as norathyriol tetraacetate on arachidonate-induced aggregation. 3-[3-(Cyclohexylamino)-2-hydroxypropoxy]xanthone showed more potent antiplatelet effects than norathyriol tetraacetate on collagen-induced aggregation. The various amino groups

  合成了一系列简单的黄嘌呤氧基丙醇胺和相关化合物。3- [3-（环丙基氨基）丙氧基] -an吨酮对花生四烯酸酯诱导的聚集表现出与降冰片四醇四乙酸酯相同的有效抗血小板作用。3- [3-（环己基氨基）-2-羟基丙氧基]黄酮在胶原蛋白诱导的聚集方面显示出比降冰片四乙酸四乙酸酯更有效的抗血小板作用。合成化合物的氧丙醇胺或氧丙胺侧链的各种氨基调节抗血小板作用。
• Synthesis, Antiplatelet and Vasorelaxing Activities of Xanthone Derivatives
  作者：Kai-Wei Lin、Song-Chwan Fang、Chi-Feng Hung、Bor-Jinn Shieh、Shyh-Chyun Yang、Che-Ming Teng、Chun-Nan Lin

  DOI：10.1002/ardp.200800002

  日期：2009.1

  A series of ω‐aminoalkoxylxanthones was synthesized and tested in vitro for their ability to inhibit platelet aggregation and cause vasorelaxing action. Compounds 4, 5, 12, 17, and 18 showed significant antiplatelet effects on thrombin‐, arachidonic acid (AA)‐, collagen‐, and platelet activating factor (PAF)‐induced washed rabbit platelet aggregation and exhibited inhibition of primary and secondary

  合成了一系列 ω-氨基烷氧基氧杂蒽酮，并在体外测试了它们抑制血小板聚集和引起血管舒张作用的能力。化合物 4、5、12、17 和 18 对凝血酶、花生四烯酸 (AA)、胶原蛋白和血小板活化因子 (PAF) 诱导的兔血小板聚集显示出显着的抗血小板作用，并显示出对初级和次级聚集的抑制作用由人富血小板血浆 (PRP) 中的 5'-二磷酸腺苷 (ADP) 诱导。化合物 4、17 和 18 在大鼠胸主动脉中显示出血管舒张活性。我们得出结论，这些化合物可能被开发为新的抗血栓剂。
• Synthesis and Antiplatelet Effects of ω-Aminoalkoxylxanthones
  作者：Chun-Nan Lin、Shorong-Shii Liou、Shih-Chen Lai、Hsien-Cheng Lin、Feng-Nien Ko、Hong-Wen Liu、Che-Ming Teng

  DOI：10.1111/j.2042-7158.1995.tb06720.x

  日期：2011.4.12

  A series of ω-aminoalkoxylxanthones were synthesized and tested in-vitro for their ability to inhibit aggregation of rabbit washed platelets and human platelet-rich plasma (PRP) induced by various inducers. Nine of these compounds showed more potent antiplatelet effects than natural norathyriol tetraacetate on collagen-induced aggregation. The various ω-aminoalkoxyl side chains of the synthesized compounds modified the antiplatelet effects. All the compounds tested in human PRP showed significant inhibition of secondary aggregation induced by adrenaline, suggesting that the antiplatelet effects of these compounds is mainly due to an inhibitory effect on thromboxane formation. These compounds at high concentration also cause vasorelaxing action in rat thoracic aorta.

  合成了一系列ω-氨基烷氧基黄酮，并在体外测试了它们抑制兔洗涤血小板和人血小板富集浆（PRP）在不同诱导剂作用下的聚集能力。其中有九种化合物比天然的四乙酰基诺芩醇对胶原诱导的聚集具有更强的抗血小板作用。合成化合物的各种ω-氨基烷氧基侧链修饰了抗血小板作用。在人类PRP中测试的所有化合物都显示出显著的抑制肾上腺素诱导的二次聚集，表明这些化合物的抗血小板作用主要是通过抑制血栓素形成的作用。这些化合物在高浓度下还会在大鼠胸主动脉中产生血管松弛作用。