2-乙酰氨基-3-(3,4-二乙酰氧基苯基)-2-丙烯酸 | 65329-03-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-乙酰氨基-3-(3,4-二乙酰氧基苯基)-2-丙烯酸
• 英文名称: α-acetylamino-β-(3,4-diacetoxyphenyl)acrylic acid
• 英文别名: β-(3,4-diacetoxyphenyl)-α-acetamidoacrylic acid；2-Acetamido-3-(3,4-diacetyloxyphenyl)prop-2-enoic acid
• CAS: 65329-03-5
• 化学式: C₁₅H₁₅NO₇
• 分子量: 321.287
• InChiKey: AAJVHBSGWUAGPJ-UHFFFAOYSA-N

物化性质

• 熔点：
  187-188°C
• 溶解度：
  可溶于氯仿、二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-乙酰氨基-3-(3,4-二乙酰氧基苯基)-2-丙烯酸 在 盐酸 、 10% Pd/C 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 20.0~100.0 ℃ 、1.52 MPa 条件下， 反应 30.0h， 生成 2-acetoxy-3-(3,4-diacetoxyphenyl)propanoic acid
  参考文献：
  名称：

  The synthesis and biological evaluation of novel Danshensu–cysteine analog conjugates as cardiovascular-protective agents

  摘要：

  A series of novel amide and thioester conjugates between Danshensu and cysteine derivatives have been designed and synthesized based on the strategy of "medicinal chemical hybridization". Pharmacological evaluation indicated that the amide conjugates 3a/4a/17a and thioester conjugates 6a-d exhibited obvious protective effects on H2O2-induced human umbilical vein endothelial cells (HUVECs). Pretreated with these conjugates could increase glutathione (GSH) activity and decrease malondialdehyde (MDA) level. Further study on mechanism of compound 4a revealed that it was related to its mitochondrial-protective effect and regulation of apoptosis-related proteins expression (Bax, p53, PARP, caspase-3, caspase-9 and Bcl-2). These results indicate that these Danshensu-cysteine analog conjugates possess significant cardiovascular-protective effects and merit further investigation. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.016
• 作为产物：
  描述：

  2-methyl-4-(3,4-diacetoxybenzylidene)oxazolone 在 水 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以88%的产率得到2-乙酰氨基-3-(3,4-二乙酰氧基苯基)-2-丙烯酸
  参考文献：
  名称：

  Green Synthesis of b-(3,4-Dihydroxyphenyl)lactic Acid

  摘要：

  开发了一种合成b-(3,4-二羟基苯基)乳酸的新方法，b-(3,4-二羟基苯基)乳酸是治疗心肌缺血的活性成分。 Pd/C催化剂被用于关键的还原反应，以取代传统使用的有毒Zn/Hg催化剂。通过采用正交实验设计，当反应温度、催化剂（5% Pd/C）用量和压力为60 ℃、20 wt%和1.0 MPa时，在最佳反应条件下获得了99.7 %的显着高产物收率，分别。

  DOI：

  10.14233/ajchem.2013.14496

文献信息

• SUBSTITUTED BETA-PHENYL-ALPHA-HYDROXY PROPANOIC ACID, SYNTHESIS METHOD AND USE THEREOF
  申请人：Northwest University

  公开号：EP2019090B1

  公开（公告）日：2012-11-14
• The synthesis and biological evaluation of novel Danshensu–cysteine analog conjugates as cardiovascular-protective agents
  作者：Yaoling Jia、Xiaoyi Dong、Pengfei Zhou、Xinhua Liu、Lilong Pan、Hong Xin、Yi Zhun Zhu、Yang Wang

  DOI：10.1016/j.ejmech.2012.07.016

  日期：2012.9

  A series of novel amide and thioester conjugates between Danshensu and cysteine derivatives have been designed and synthesized based on the strategy of "medicinal chemical hybridization". Pharmacological evaluation indicated that the amide conjugates 3a/4a/17a and thioester conjugates 6a-d exhibited obvious protective effects on H2O2-induced human umbilical vein endothelial cells (HUVECs). Pretreated with these conjugates could increase glutathione (GSH) activity and decrease malondialdehyde (MDA) level. Further study on mechanism of compound 4a revealed that it was related to its mitochondrial-protective effect and regulation of apoptosis-related proteins expression (Bax, p53, PARP, caspase-3, caspase-9 and Bcl-2). These results indicate that these Danshensu-cysteine analog conjugates possess significant cardiovascular-protective effects and merit further investigation. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Green Synthesis of b-(3,4-Dihydroxyphenyl)lactic Acid
  作者：Qun-Zheng Zhang、Yi Wang、Ye-Fei Nan、Xun-Yu Xiong、Qing Pan、Xun-Li Zhang

  DOI：10.14233/ajchem.2013.14496

  日期：——

  A new method has been developed for the synthesis of b-(3,4-dihydroxyphenyl)lactic acid, an active ingredient for the treatment of myocardial ischemia. Pd/C catalysts were used in the key reduction reaction to replace the traditionally used toxic Zn/Hg catalysts. A significantly high product yield of 99.7 % was obtained under the optimal reaction conditions, through the use of orthogonal experimental design, when reaction temperature, catalyst (5 % Pd/C) amount and pressure were 60 ºC, 20 wt % and 1.0 MPa, respectively.

  开发了一种合成b-(3,4-二羟基苯基)乳酸的新方法，b-(3,4-二羟基苯基)乳酸是治疗心肌缺血的活性成分。 Pd/C催化剂被用于关键的还原反应，以取代传统使用的有毒Zn/Hg催化剂。通过采用正交实验设计，当反应温度、催化剂（5% Pd/C）用量和压力为60 ℃、20 wt%和1.0 MPa时，在最佳反应条件下获得了99.7 %的显着高产物收率，分别。