1-<<3-(methylsulfonyloxy)propyl>amino>anthraquinone | 131011-94-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-<<3-(methylsulfonyloxy)propyl>amino>anthraquinone
• 英文别名: 1-[3-[(methylsulfonyl)oxy]propylamino]-9,10-anthracenedione；1-{[3-(methylsulfonyloxy)propyl]amino}anthraquinone；3-[(9,10-Dioxoanthracen-1-yl)amino]propyl methanesulfonate
• CAS: 131011-94-4
• 化学式: C₁₈H₁₇NO₅S
• 分子量: 359.403
• InChiKey: JEHVCHVNXSBGHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-<<3-(methylsulfonyloxy)propyl>amino>anthraquinone 、 羟乙基乙二胺 以 氯仿 为溶剂， 反应 24.0h， 以70%的产率得到1-<<3-<<2-<(2-hydroxyethyl)amino>ethyl>amino>propyl>amino>anthraquinone
  参考文献：
  名称：

  一系列与蒽醌嵌入剂连接的顺式-PtCl2复合物的制备，表征和抗癌活性。

  摘要：

  一系列新的顺式-PtL2X2型配合物[其中L是单齿AQ-Y（CH2）nNH2，L2是双齿AQ-Y（CH2）nNH（CH2）2NH2；AQ =蒽醌，X = Cl，I，Y = NH，O]，其中蒽醌嵌入剂通过（氨基烷基）氨基，（氧基烷基）氨基或聚乙二醇（氨基乙基）氨基连接链束缚在顺式PtCl2单元上制备并体外筛选抗P388白血病。对选定的复合物进行了体内毒性研究。通过元素分析，195Pt NMR光谱和FTIR对所有配合物进行表征。1：1 Pt-嵌入剂复合物显示出比1：2 Pt-嵌入剂复合物更高的体外细胞毒性活性。二氯化物配合物始终比二碘化物对应物更具活性。在1：具有较短连接链（n = 2、3）的1 Pt-嵌入剂复合物表现出最高的细胞毒活性。三种化合物，[[[2-[[2-（蒽醌-1-基氨基）乙基]氨基]乙基]胺-N，N']二氯铂（II），[[2-[[3-（蒽醌-1-基氨基） ）丙基]氨基]乙基]胺

  DOI：

  10.1021/jm00105a063
• 作为产物：
  描述：

  1-氯蒽醌 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 作用下， 以 二氯甲烷 、 正丁醇 为溶剂， 反应 52.0h， 生成 1-<<3-(methylsulfonyloxy)propyl>amino>anthraquinone
  参考文献：
  名称：

  Novel anthraquinone derivatives with redox-active functional groups capable of producing free radicals by metabolism: are free radicals essential for cytotoxicity?

  摘要：

  The mode of action of antitumour anthraquinone derivatives (i.e. mitoxantrone) is not clearly established yet. It includes, among others, intercalation and binding to DNA, bioreduction and aerobic redox cycling. A series of anthraquinone derivatives, with potentially bioreducible groups sited in the side chain, have been synthesized and biologically evaluated. Their redox and cytotoxic activities were screened. Derivatives which bear a 2-(dimethylamino)ethylamino substituent, known to confer high DNA affinity, demonstrated cytotoxicity but not redox activity (beside the anthraquinone reduction). Conversely, derivatives which showed redox activity were not cytotoxic toward the P388 cell line. The results suggest that bioreduction is not the main mode of action in the cytotoxicity of anthraquinones. (C) 1999 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)80029-x

文献信息

• Novel anthraquinone derivatives with redox-active functional groups capable of producing free radicals by metabolism: are free radicals essential for cytotoxicity?
  作者：Dinorah Barasch、Omer Zipori、Israel Ringel、Isaac Ginsburg、Amram Samuni、Jehoshua Katzhendler

  DOI：10.1016/s0223-5234(00)80029-x

  日期：1999.7

  The mode of action of antitumour anthraquinone derivatives (i.e. mitoxantrone) is not clearly established yet. It includes, among others, intercalation and binding to DNA, bioreduction and aerobic redox cycling. A series of anthraquinone derivatives, with potentially bioreducible groups sited in the side chain, have been synthesized and biologically evaluated. Their redox and cytotoxic activities were screened. Derivatives which bear a 2-(dimethylamino)ethylamino substituent, known to confer high DNA affinity, demonstrated cytotoxicity but not redox activity (beside the anthraquinone reduction). Conversely, derivatives which showed redox activity were not cytotoxic toward the P388 cell line. The results suggest that bioreduction is not the main mode of action in the cytotoxicity of anthraquinones. (C) 1999 Editions scientifiques et medicales Elsevier SAS.
• Preparation, characterization, and anticancer activity of a series of cis-PtCl2 complexes linked to anthraquinone intercalators
  作者：Dan Gibson、Keria Fiorella Gean、Jehoshua Katzhendle、Raphael Ben-Shoshan、Avner Ramu、Israel Ringel

  DOI：10.1021/jm00105a063

  日期：1991.1

  A new series of complexes of the type cis-PtL2X2 [where L is a monodentate AQ-Y(CH2)nNH2 and L2 is a bidentate AQ-Y(CH2)nNH(CH2)2NH2; AQ = anthraquinone, X = Cl, I, Y = NH, O] in which anthraquinone intercalators are tethered to the cis-PtCl2 unit via an (aminoalkyl)amino, (oxyalkyl)amino, or polyethylene glycol (aminoethyl)amino linker chains was prepared and screened in vitro against P388 leukemia

  一系列新的顺式-PtL2X2型配合物[其中L是单齿AQ-Y（CH2）nNH2，L2是双齿AQ-Y（CH2）nNH（CH2）2NH2；AQ =蒽醌，X = Cl，I，Y = NH，O]，其中蒽醌嵌入剂通过（氨基烷基）氨基，（氧基烷基）氨基或聚乙二醇（氨基乙基）氨基连接链束缚在顺式PtCl2单元上制备并体外筛选抗P388白血病。对选定的复合物进行了体内毒性研究。通过元素分析，195Pt NMR光谱和FTIR对所有配合物进行表征。1：1 Pt-嵌入剂复合物显示出比1：2 Pt-嵌入剂复合物更高的体外细胞毒性活性。二氯化物配合物始终比二碘化物对应物更具活性。在1：具有较短连接链（n = 2、3）的1 Pt-嵌入剂复合物表现出最高的细胞毒活性。三种化合物，[[[2-[[2-（蒽醌-1-基氨基）乙基]氨基]乙基]胺-N，N']二氯铂（II），[[2-[[3-（蒽醌-1-基氨基） ）丙基]氨基]乙基]胺