3-(1,3-benzodioxol-5-yl)-2-hydroxyprop-2-enoic acid | 143815-53-6

• 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: 3-(1,3-benzodioxol-5-yl)-2-hydroxyprop-2-enoic acid
• CAS: 143815-53-6
• 化学式: C₁₀H₈O₅
• 分子量: 208.171
• InChiKey: QVGXMDVKXQOZLG-UHFFFAOYSA-N

物化性质

• 沸点：
  421.2±45.0 °C(Predicted)
• 密度：
  1.559±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(1,3-benzodioxol-5-yl)-2-hydroxyprop-2-enoic acid 在 10% Pd/C 、 氢气 、 乙酸酐 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 30.0h， 生成 3-[3,4-(亚甲二氧基)苯基]丙酸
  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：

  β-(benzo[1,3]dioxol-5-yl)-α-acetamidoacrylic acid 在 盐酸 作用下， 以 水 为溶剂， 以96%的产率得到3-(1,3-benzodioxol-5-yl)-2-hydroxyprop-2-enoic 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

文献信息

• 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.