4-<(tert-buthoxycarbonyl)methyl>-β-N-phthalimidostyrene | 116856-62-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 4-<(tert-buthoxycarbonyl)methyl>-β-N-phthalimidostyrene
• 英文别名: 4-[(tert-buthoxycarbonyl)methyl]-β-N-phthalimidostyrene；tert-butyl 2-[4-[(E)-2-(1,3-dioxoisoindol-2-yl)ethenyl]phenyl]acetate
• CAS: 116856-62-3
• 化学式: C₂₂H₂₁NO₄
• 分子量: 363.413
• InChiKey: GFQMAKREPLEGHM-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-<(tert-buthoxycarbonyl)methyl>-β-N-phthalimidostyrene 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 {4-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-phenyl}-acetic acid tert-butyl ester
  参考文献：
  名称：

  2-(Arylalkylamino)adenosin-5'-uronamides: a new class of highly selective adenosine A2 receptor ligands

  摘要：

  The synthesis and receptor-binding profiles at adenosine receptor subtypes for a series of 2-(arylalkylamino)-adenosin-5'-uronamides is described. Halogenated 2-phenethylamino analogues such as 3e show greater than 200-fold selectivity for the A2 receptor subtype on the basis of rat brain receptor binding. The general structure-activity relationship of this series of compounds is discussed both in terms of potency at A2 receptors as well as receptor subtype selectivity. It is possible to introduce a hydrophilic carboxyalkyl substituent to this series such as in CGS 21680A (3h) and still retain good potency and selectivity for A2 receptors. In addition, functional data in a perfused working rat heart model shows that these compounds possess full agonist properties at A2 receptors with 3h having a greater than 1500-fold separation between A2 (coronary vasodilatory) and A1 (negative chronotropic) receptor mediated events.

  DOI：

  10.1021/jm00169a015
• 作为产物：
  描述：

  N-乙烯基邻苯亚胺 、 2-(4-溴苯基)乙酸叔丁酯 在 palladium diacetate 、 三(邻甲基苯基)磷 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以87%的产率得到4-<(tert-buthoxycarbonyl)methyl>-β-N-phthalimidostyrene
  参考文献：
  名称：

  2-(Arylalkylamino)adenosin-5'-uronamides: a new class of highly selective adenosine A2 receptor ligands

  摘要：

  The synthesis and receptor-binding profiles at adenosine receptor subtypes for a series of 2-(arylalkylamino)-adenosin-5'-uronamides is described. Halogenated 2-phenethylamino analogues such as 3e show greater than 200-fold selectivity for the A2 receptor subtype on the basis of rat brain receptor binding. The general structure-activity relationship of this series of compounds is discussed both in terms of potency at A2 receptors as well as receptor subtype selectivity. It is possible to introduce a hydrophilic carboxyalkyl substituent to this series such as in CGS 21680A (3h) and still retain good potency and selectivity for A2 receptors. In addition, functional data in a perfused working rat heart model shows that these compounds possess full agonist properties at A2 receptors with 3h having a greater than 1500-fold separation between A2 (coronary vasodilatory) and A1 (negative chronotropic) receptor mediated events.

  DOI：

  10.1021/jm00169a015

文献信息

• HUTCHISON, ALAN J.;WILLIAMS, MICHAEL;JESUS, REYNALDA DE;RINA, YOKOYAMA;OE+, J. MED. CHEM., 33,(1990) N, C. 1919-1924
  作者：HUTCHISON, ALAN J.、WILLIAMS, MICHAEL、JESUS, REYNALDA DE、RINA, YOKOYAMA、OE+

  DOI：——

  日期：——