3-[(6-bromohexyl)oxy]-9H-xanthen-9-one | 473000-09-8

• 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-[(6-bromohexyl)oxy]-9H-xanthen-9-one
• 英文别名: 3-(6-Bromohexoxy)xanthen-9-one；3-(6-bromohexoxy)xanthen-9-one
• CAS: 473000-09-8
• 化学式: C₁₉H₁₉BrO₃
• 分子量: 375.262
• InChiKey: YULIPLWAJVIOMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-羟基蒽醌 、 3-[(6-bromohexyl)oxy]-9H-xanthen-9-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以96%的产率得到2-({6-[(9-oxo-9H-xanthen-3-yl)oxy]hexyl}oxy)anthracene-9,10-dione
  参考文献：
  名称：

  Synthesis and Cytotoxic Evaluation of Potential Bis-Intercalators: Tetramethylenebis(oxy)- and Hexamethylenebis(oxy)-Linked Assemblies Consisting of Flavone, Xanthone, Anthraquinone, and Dibenzofuran

  摘要：

  In a search for potential inhibitors of solid-tumor growth. certain alkanediylbis(oxy)-linked assemblies were synthesized kind evaluated for their cytotoxicity as bis-intercalators. Symmetrical assemblies 1b-12b were synthesized front their respective Aryl-OH and either dibromobutane or dibromohexane, while unsymmetrical ones 13-15 were prepared front Aryl(1)-OH and either Aryl(2)-O-(CH2)(4)Br or Aryl(2)-O-(CH2)(6)Br. These bis-intercalators were inactive against the growth of leukemia cells. However, some of them were active against the growth of certain solid tumors such as HOP-62, HOP-92 (non-small-cell lung cancer), SF-265, SNB-75, U251 (CNS cancer), A498 (renal cancer), and HS578T (breast cancer). Among them, [hexane-1,6-diylbis(oxy)bis(4,1-phenylene)]bis[4H-1-benzopyran] (6b) was especially active against the growth of all CNS cancer cell lines and also the growth of A498, HOP-62, and HOP-92 with GI(50) values of 17.0. 20.0, and 21.8 mum, respectively.

  DOI：

  10.1002/1522-2675(200205)85:5<1382::aid-hlca1382>3.0.co;2-y
• 作为产物：
  描述：

  1,6-二溴己烷 、 西伯尔链接剂 在 氢氧化钾 、 碘 作用下， 以 水 、 叔丁醇 为溶剂， 反应 3.0h， 生成 3-[(6-bromohexyl)oxy]-9H-xanthen-9-one
  参考文献：
  名称：

  氧杂蒽酮衍生物的合成、抗血小板和血管舒张活性

  摘要：

  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。

  DOI：

  10.1002/ardp.200800002

文献信息

• 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 Cytotoxic Evaluation of Potential Bis-Intercalators: Tetramethylenebis(oxy)- and Hexamethylenebis(oxy)-Linked Assemblies Consisting of Flavone, Xanthone, Anthraquinone, and Dibenzofuran
  作者：Tai-Chi Wang、Yue-Ling Zhao、Shorong-Shii Liou

  DOI：10.1002/1522-2675(200205)85:5<1382::aid-hlca1382>3.0.co;2-y

  日期：2002.5

  In a search for potential inhibitors of solid-tumor growth. certain alkanediylbis(oxy)-linked assemblies were synthesized kind evaluated for their cytotoxicity as bis-intercalators. Symmetrical assemblies 1b-12b were synthesized front their respective Aryl-OH and either dibromobutane or dibromohexane, while unsymmetrical ones 13-15 were prepared front Aryl(1)-OH and either Aryl(2)-O-(CH2)(4)Br or Aryl(2)-O-(CH2)(6)Br. These bis-intercalators were inactive against the growth of leukemia cells. However, some of them were active against the growth of certain solid tumors such as HOP-62, HOP-92 (non-small-cell lung cancer), SF-265, SNB-75, U251 (CNS cancer), A498 (renal cancer), and HS578T (breast cancer). Among them, [hexane-1,6-diylbis(oxy)bis(4,1-phenylene)]bis[4H-1-benzopyran] (6b) was especially active against the growth of all CNS cancer cell lines and also the growth of A498, HOP-62, and HOP-92 with GI(50) values of 17.0. 20.0, and 21.8 mum, respectively.
• 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。