2-<(Z)-3-(benzylamino)-3-oxo-1-propenyl>phenyl acetate | 208402-14-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-<(Z)-3-(benzylamino)-3-oxo-1-propenyl>phenyl acetate
• 英文别名: [2-[(Z)-3-(benzylamino)-3-oxoprop-1-enyl]phenyl] acetate
• CAS: 208402-14-6
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: LYJRQBSNWYBPBT-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<(Z)-3-(benzylamino)-3-oxo-1-propenyl>phenyl acetate 在 硫酸氢铵 、 phosphate buffer 、 carboxylic ester hydrolase 作用下， 以 水 为溶剂， 生成 香豆素
  参考文献：
  名称：

  基于香豆素的前药。第3部分：结构对胺的酯酶敏感性前药释放动力学的影响。

  摘要：

  为了研究对香豆素基酯酶敏感的前药系统的释放动力学的结构影响，合成了酯“触发”部分和胺“药物”部分具有不同结构特征的两个系列化合物。在猪肝酯酶存在下，这九种模型前药的半衰期为约2分钟至190分钟。酰基的空间体积似乎对酯酶触发的胺从模型前药中释放的半衰期影响很小。内酯化的速率取决于胺部分的空间和电子性质。

  DOI：

  10.1016/s0968-0896(98)00014-5
• 作为产物：
  描述：

  反式-2-羟基肉桂酸 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 31.0h， 生成 2-<(Z)-3-(benzylamino)-3-oxo-1-propenyl>phenyl acetate
  参考文献：
  名称：

  Two new improved approaches to the synthesis of coumarin-based prodrugs

  摘要：

  Our laboratory has recently reported the development of a coumarin-based, esterase-sensitive prodrug system for the preparation of prodrugs of amines, peptides, and peptidomimetics. Biological evaluations including animal studies have demonstrated me clinical potential of this prodrug system. However, the original synthetic method used required a long sequence of reactions with a relatively low overall yield. In this report, we describe two new approaches to the synthesis of these coumarin-based prodrugs. The first approach is a photochemical approach taking advantage of the photoisomerization of cinnamic acid and its derivatives. The second approach is through the catalytic hydrogenation of a triple bond for the generation of me cis double bond in the coumarinic acid moiety. Both approaches allow for the synthesis of these prodrugs in fewer steps with much improved overall yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00121-0

文献信息

• Chemical feasibility studies of a potential coumarin-based prodrug system
  作者：Binghe Wang、Huijuan Zhang、Wei Wang

  DOI：10.1016/0960-894x(96)00147-3

  日期：1996.4
• Two new improved approaches to the synthesis of coumarin-based prodrugs
  作者：Ailian Zheng、Wei Wang、Huijuan Zhang、Binghe Wang

  DOI：10.1016/s0040-4020(99)00121-0

  日期：1999.4

  Our laboratory has recently reported the development of a coumarin-based, esterase-sensitive prodrug system for the preparation of prodrugs of amines, peptides, and peptidomimetics. Biological evaluations including animal studies have demonstrated me clinical potential of this prodrug system. However, the original synthetic method used required a long sequence of reactions with a relatively low overall yield. In this report, we describe two new approaches to the synthesis of these coumarin-based prodrugs. The first approach is a photochemical approach taking advantage of the photoisomerization of cinnamic acid and its derivatives. The second approach is through the catalytic hydrogenation of a triple bond for the generation of me cis double bond in the coumarinic acid moiety. Both approaches allow for the synthesis of these prodrugs in fewer steps with much improved overall yield. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Coumarin-based prodrugs. Part 3: Structural effects on the release kinetics of esterase-sensitive prodrugs of amines 1 1Part of this work was performed at the University of Oklahoma Health Sciences Center, College of Pharmacy.
  作者：Binghe Wang、Huijuan Zhang、Ailian Zheng、Wei Wang

  DOI：10.1016/s0968-0896(98)00014-5

  日期：1998.4

  structural effects on the release kinetics of a coumarin-based esterase-sensitive prodrug system, two series of compounds with varying structural features of the ester 'trigger' part and the amine 'drug' part were synthesized. The half-lives of the nine model prodrugs in the presence of porcine liver esterase ranged from about 2 min to 190 min. The steric bulkiness of the acyl group seems to have only a

  为了研究对香豆素基酯酶敏感的前药系统的释放动力学的结构影响，合成了酯“触发”部分和胺“药物”部分具有不同结构特征的两个系列化合物。在猪肝酯酶存在下，这九种模型前药的半衰期为约2分钟至190分钟。酰基的空间体积似乎对酯酶触发的胺从模型前药中释放的半衰期影响很小。内酯化的速率取决于胺部分的空间和电子性质。