1,11-bis(2,4-dibenzyloxyphenyl)-4,8-dioxaundecane | 491610-78-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,11-bis(2,4-dibenzyloxyphenyl)-4,8-dioxaundecane
• 英文别名: 1-[3-[3-[3-[2,4-bis(phenylmethoxy)phenyl]propoxy]propoxy]propyl]-2,4-bis(phenylmethoxy)benzene
• CAS: 491610-78-7
• 化学式: C₄₉H₅₂O₆
• 分子量: 736.948
• InChiKey: DEJKDHRJOOILKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  55
• 可旋转键数：
  24
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,11-bis(2,4-dibenzyloxyphenyl)-4,8-dioxaundecane 在 盐酸羟胺 、 三乙胺 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Desferrithiocin Analogue Based Hexacoordinate Iron(III) Chelators

  摘要：

  Traditional thinking has been that hexacoordinate Fe(III) ligands are more effective at preventing iron's interactions with reactive oxygen species, most particularly the Fe(II)-mediated reduction of hydrogen peroxide to the hydroxyl radical (i.e., Fenton chemistry), than are ligands of lower denticity. Thus, a hexacoordinate derivative of the well-characterized tricoordinate ligand (S)-2-(2,4-dihydroxyphenyl)-4,5-dihydro-4-thiazolecarboxylic acid [4'-(HO)-DADMDFT], (S,S)-1,11-bis[5-(4-carboxy-4,5-dihydrothiazol-2-yl)-2,4-dihydroxyphenyl]-4,8-dioxaundecane, was designed with the aid of a molecular modeling program and synthesized, Evaluations both in vitro and in vivo were carried out to determine whether there is any advantage, at the level of prevention of Fenton chemistry, radical trapping, or iron clearance, to constructing a desferrithiocin-based hexacoordinate analogue. The hexacoordinate analogue was more effective at preventing the iron-mediated oxidation of ascorbate at low ligand/metal ratios than was its tricoordinate parent and can function as an excellent radical scavenger. At equivalent iron binding doses in the bile duct cannulated rodent, oral administration of the tricoordinate ligand was Mold more effective than was po administration of the hexacoordinate derivative. However, se administration of the hexacoordinate derivative resulted in an efficiency that was 3 times greater than that of the tricoordinate chelator. Unfortunately, the rodent findings were not substantiated in the primates. The hexacoordinate ligand was only about one-half as efficient as its tricoordinate parent when administered so. Owing to these results, po dosing was not attempted. Thus, there appears to be no overall advantage to coupling two molecules of 4 (HO)-DADMDFT to afford a hexacoordinate derivative.

  DOI：

  10.1021/jm020184n
• 作为产物：
  描述：

  3-(2',4'-di(benzyloxy)phenyl)propanol 在 吡啶 、 氢氧化钾 、 lithium bromide 作用下， 以 二氯甲烷 、 二甲基亚砜 、 丙酮 为溶剂， 反应 1.0h， 生成 1,11-bis(2,4-dibenzyloxyphenyl)-4,8-dioxaundecane
  参考文献：
  名称：

  Desferrithiocin Analogue Based Hexacoordinate Iron(III) Chelators

  摘要：

  Traditional thinking has been that hexacoordinate Fe(III) ligands are more effective at preventing iron's interactions with reactive oxygen species, most particularly the Fe(II)-mediated reduction of hydrogen peroxide to the hydroxyl radical (i.e., Fenton chemistry), than are ligands of lower denticity. Thus, a hexacoordinate derivative of the well-characterized tricoordinate ligand (S)-2-(2,4-dihydroxyphenyl)-4,5-dihydro-4-thiazolecarboxylic acid [4'-(HO)-DADMDFT], (S,S)-1,11-bis[5-(4-carboxy-4,5-dihydrothiazol-2-yl)-2,4-dihydroxyphenyl]-4,8-dioxaundecane, was designed with the aid of a molecular modeling program and synthesized, Evaluations both in vitro and in vivo were carried out to determine whether there is any advantage, at the level of prevention of Fenton chemistry, radical trapping, or iron clearance, to constructing a desferrithiocin-based hexacoordinate analogue. The hexacoordinate analogue was more effective at preventing the iron-mediated oxidation of ascorbate at low ligand/metal ratios than was its tricoordinate parent and can function as an excellent radical scavenger. At equivalent iron binding doses in the bile duct cannulated rodent, oral administration of the tricoordinate ligand was Mold more effective than was po administration of the hexacoordinate derivative. However, se administration of the hexacoordinate derivative resulted in an efficiency that was 3 times greater than that of the tricoordinate chelator. Unfortunately, the rodent findings were not substantiated in the primates. The hexacoordinate ligand was only about one-half as efficient as its tricoordinate parent when administered so. Owing to these results, po dosing was not attempted. Thus, there appears to be no overall advantage to coupling two molecules of 4 (HO)-DADMDFT to afford a hexacoordinate derivative.

  DOI：

  10.1021/jm020184n

文献信息

• Antioxidant and radical scavenging activity of synthetic analogs of desferrithiocin
  申请人：University of Florida

  公开号：US20040044220A1

  公开（公告）日：2004-03-04

  Free radicals and reactive oxygen species have the potential to damage a wide variety of organic molecules, typically by oxidizing certain moieties. These damaging species can, for example, be produced by an organism as a by-product of cellular respiration or by the reaction of iron(II) and peroxide. The present invention includes methods of using aryl-substituted heterocyclic iron chelating compounds as antioxidants, as well as preventing the reduction of iron(III) to iron(II). In addition, the present invention provides methods of treating conditions such as inflammatory disease, neoplastic disease, and ischemic episodes.

  自由基和反应性氧化物具有损坏各种有机分子的潜力，通常通过氧化某些官能团来实现。这些有害的物质可以由生物体作为细胞呼吸的副产品产生，也可以由铁（II）和过氧化物的反应产生。本发明包括使用芳基取代的杂环铁螯合化合物作为抗氧化剂的方法，以及防止铁（III）还原为铁（II）的方法。此外，本发明还提供了治疗炎症性疾病、肿瘤性疾病和缺血发作的方法。
• Desferrithiocin Analogue Based Hexacoordinate Iron(III) Chelators
  作者：Raymond J. Bergeron、Guangfei Huang、William R. Weimar、Richard E. Smith、Jan Wiegand、James S. McManis

  DOI：10.1021/jm020184n

  日期：2003.1.1

  Traditional thinking has been that hexacoordinate Fe(III) ligands are more effective at preventing iron's interactions with reactive oxygen species, most particularly the Fe(II)-mediated reduction of hydrogen peroxide to the hydroxyl radical (i.e., Fenton chemistry), than are ligands of lower denticity. Thus, a hexacoordinate derivative of the well-characterized tricoordinate ligand (S)-2-(2,4-dihydroxyphenyl)-4,5-dihydro-4-thiazolecarboxylic acid [4'-(HO)-DADMDFT], (S,S)-1,11-bis[5-(4-carboxy-4,5-dihydrothiazol-2-yl)-2,4-dihydroxyphenyl]-4,8-dioxaundecane, was designed with the aid of a molecular modeling program and synthesized, Evaluations both in vitro and in vivo were carried out to determine whether there is any advantage, at the level of prevention of Fenton chemistry, radical trapping, or iron clearance, to constructing a desferrithiocin-based hexacoordinate analogue. The hexacoordinate analogue was more effective at preventing the iron-mediated oxidation of ascorbate at low ligand/metal ratios than was its tricoordinate parent and can function as an excellent radical scavenger. At equivalent iron binding doses in the bile duct cannulated rodent, oral administration of the tricoordinate ligand was Mold more effective than was po administration of the hexacoordinate derivative. However, se administration of the hexacoordinate derivative resulted in an efficiency that was 3 times greater than that of the tricoordinate chelator. Unfortunately, the rodent findings were not substantiated in the primates. The hexacoordinate ligand was only about one-half as efficient as its tricoordinate parent when administered so. Owing to these results, po dosing was not attempted. Thus, there appears to be no overall advantage to coupling two molecules of 4 (HO)-DADMDFT to afford a hexacoordinate derivative.