3-(2,4-dibenzyloxyphenyl)propyl p-tosylate | 491610-76-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(2,4-dibenzyloxyphenyl)propyl p-tosylate
• 英文别名: 3-[2,4-Bis(phenylmethoxy)phenyl]propyl 4-methylbenzenesulfonate
• CAS: 491610-76-5
• 化学式: C₃₀H₃₀O₅S
• 分子量: 502.631
• InChiKey: OYNUTOBVNQSKIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2,4-dibenzyloxyphenyl)propyl p-tosylate 在 sodium hydride 、 1,3-丙二醇 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2,4-Bis(phenylmethoxy)-1-prop-2-enylbenzene
  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：

  2-(2',4'-di(benzyloxy)phenyl)acetaldehyde 在 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 水 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 39.0h， 生成 3-(2,4-dibenzyloxyphenyl)propyl p-tosylate
  参考文献：
  名称：

  间苯二酚烷基糖苷、羟烷基间苯二酚、烷基间苯二酚的化学合成及酪氨酸酶抑制活性

  摘要：

  为了开发新型酪氨酸酶抑制剂，间苯二酚烷基葡糖苷7 – 12通过 Wittig 和/或 Horner-Wadsworth-Emmons 反应合成，其中 Koenigs-Knorr 糖基化是关键步骤。对于酪氨酸酶催化的氧化，观察到 7-12 的半数最大抑制浓度 (IC 50 ) 为35.9-0.39 µM。还评估了羟烷基间苯二酚13-18和烷基间苯二酚19-24的酪氨酸酶抑制活性，以研究糖对其结构的影响。因此，IC 50的13 – 18和19 – 24分别为 9.27–0.32 µM 和 1.58–0.53 µM。随着烷基链长度的增加，大多数衍生物变得更有效。C 2和C 3类似物之间的活性差距按顺序减小：间苯二酚烷基糖苷>羟烷基间苯二酚>烷基间苯二酚。这表明糖和羟基在与间苯二酚环相邻时会干扰功能。水溶性差的C 14类似物22 (IC 50  = 0.81 µM) 与 C 10类似物21 (IC

  DOI：

  10.1016/j.molstruc.2022.133668

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.
• Chemical synthesis and tyrosinase inhibitory activity of resorcinol alkyl glucosides, hydroxyalkyl resorcinols, and alkyl resorcinols
  作者：Wakana Ishioka、Ken-ichi Nihei

  DOI：10.1016/j.molstruc.2022.133668

  日期：2022.11

  length of the alkyl chain. The gap in the activities between the C2 and C3 analogs was decreased in the order: resorcinol alkyl glucosides>hydroxyalkyl resorcinols>alkyl resorcinols. It indicates that the sugar and hydroxy groups interfered in the functions when they were adjacent to the resorcinol ring. C14 analog 22 (IC50 = 0.81 µM) with the poor water solubility showed slightly weak activity compared

  为了开发新型酪氨酸酶抑制剂，间苯二酚烷基葡糖苷7 – 12通过 Wittig 和/或 Horner-Wadsworth-Emmons 反应合成，其中 Koenigs-Knorr 糖基化是关键步骤。对于酪氨酸酶催化的氧化，观察到 7-12 的半数最大抑制浓度 (IC 50 ) 为35.9-0.39 µM。还评估了羟烷基间苯二酚13-18和烷基间苯二酚19-24的酪氨酸酶抑制活性，以研究糖对其结构的影响。因此，IC 50的13 – 18和19 – 24分别为 9.27–0.32 µM 和 1.58–0.53 µM。随着烷基链长度的增加，大多数衍生物变得更有效。C 2和C 3类似物之间的活性差距按顺序减小：间苯二酚烷基糖苷>羟烷基间苯二酚>烷基间苯二酚。这表明糖和羟基在与间苯二酚环相邻时会干扰功能。水溶性差的C 14类似物22 (IC 50  = 0.81 µM) 与 C 10类似物21 (IC