(Z)-2-acetoxy-3-(3,4-diacetoxyphenyl)acrylic acid | 1162198-69-7

• 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
• 英文名称: (Z)-2-acetoxy-3-(3,4-diacetoxyphenyl)acrylic acid
• 英文别名: Triacetoxyphenylpyruvic acid；(Z)-2-acetyloxy-3-(3,4-diacetyloxyphenyl)prop-2-enoic acid
• CAS: 1162198-69-7
• 化学式: C₁₅H₁₄O₈
• 分子量: 322.271
• InChiKey: JIHNMDCGGTVLQA-AUWJEWJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (Z)-2-acetoxy-3-(3,4-diacetoxyphenyl)acrylic acid 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、500.01 kPa 条件下， 反应 24.0h， 以73%的产率得到2-acetoxy-3-(3,4-diacetoxyphenyl)propanoic acid
  参考文献：
  名称：

  丹参素与H2S/NO供体结合物及其制备方法和在制药中的应用

  摘要：

  本发明属化学制药领域，涉及中草药丹参中有效成分丹参素与H 2 S/NO供体的结合物及其制备方法和在制药中的应用，尤其是在制备防治心脑血管和炎症相关疾病药物中的用途。本发明通过体外氧化应激损伤和炎症模型实验，结果显示所述的结合物能显著抑制H 2 O 2 诱导的SH‑SY5Y细胞氧化应激损伤，对损伤细胞具有明显的保护作用；能显著抑制内毒素(LPS)诱导的小鼠腹腔巨噬细胞分泌炎性介质，减少炎症诱导的一氧化氮和炎性细胞因子的释放；体内活性实验结果显示，所述的结合物对LPS诱导的小鼠腹膜炎能改善小鼠的凝血时间，明显抑制小鼠腹腔的炎性细胞因子的释放，结果表明所述化合物可用于制备防治心脑血管疾病和炎症性疾病的药物。

  公开号：

  CN111484413A
• 作为产物：
  描述：

  3,4-二羟基苯甲醛 在 盐酸 、 sodium acetate 作用下， 反应 11.0h， 生成 (Z)-2-acetoxy-3-(3,4-diacetoxyphenyl)acrylic acid
  参考文献：
  名称：

  丹参素与H2S/NO供体结合物及其制备方法和在制药中的应用

  摘要：

  本发明属化学制药领域，涉及中草药丹参中有效成分丹参素与H 2 S/NO供体的结合物及其制备方法和在制药中的应用，尤其是在制备防治心脑血管和炎症相关疾病药物中的用途。本发明通过体外氧化应激损伤和炎症模型实验，结果显示所述的结合物能显著抑制H 2 O 2 诱导的SH‑SY5Y细胞氧化应激损伤，对损伤细胞具有明显的保护作用；能显著抑制内毒素(LPS)诱导的小鼠腹腔巨噬细胞分泌炎性介质，减少炎症诱导的一氧化氮和炎性细胞因子的释放；体内活性实验结果显示，所述的结合物对LPS诱导的小鼠腹膜炎能改善小鼠的凝血时间，明显抑制小鼠腹腔的炎性细胞因子的释放，结果表明所述化合物可用于制备防治心脑血管疾病和炎症性疾病的药物。

  公开号：

  CN111484413A

文献信息

• Asymmetric synthesis and biological evaluation of Danshensu derivatives as anti-myocardial ischemia drug candidates
  作者：Cunnan Dong、Yang Wang、Yi Zhun Zhu

  DOI：10.1016/j.bmc.2009.02.065

  日期：2009.5

  The synthesis and bioactivities of Danshensu derivatives (R)-methyl 2-acetoxy-3-(3,4-diacetoxyphenyl) propanoate (1a), (R)-methyl 2-acetoxy-3-(3,4-methylenedioxyphenyl) propanoate (1b) and their racemates 7 and 10 were reported in this paper. These derivatives were designed to improve their chemical stability and liposolubility by protecting Danshensu's phenolic hydroxyl groups with acetyl or methylene which could be readily hydrolyzed to release bioactive Danshensu. The asymmetric synthesis of 1a and 1b were achieved by catalytic hydrogenation of (Z)-methyl 2-acetoxy-3-(3,4-diacetoxyphenyl)-2-propenoate (6a) and (Z)-methyl 2-acetoxy-3-(3,4-methylenedioxyphenyl)-2-propenoate (6b) in excellent enantiomeric excesses (92% ee and 98% ee, respectively) and good yields (>89%). An unexpected intermediate product, (Z)-2-acetoxy-3-(3,4-dihydroxyphenyl) acrylic acid (4c) was obtained with high chemoselectivity in 86% yield by keeping the reaction temperature at 60 degrees C and its structure was identified by Xray single crystal diffraction analysis. 1a, 1b and their racemates 7, 10 as well as 4c exhibited potent protective activities against hypoxia-induced cellular damage. The in vitro test showed that all these compounds could increase cell viability, and inhibit lipid hyperoxidation. Furthermore, 1a and 4c could inhibit apoptosis by regulating the expression of apoptosis-related molecule in gene and protein levels, up-regulating the expression of bcl-2 and down-regulating bax and caspase-3. The in vivo test indicated that 4c exhibited anti-myocardial ischemic effects featured by reducing infarction size and increasing the level of the intracellular enzymes detectable in serum. Therefore, these Danshensu derivatives may be good drug candidates for anti-myocardial ischemia therapy and merit further investigation. (C) 2009 Elsevier Ltd. All rights reserved.
• 丹参素与H2S/NO供体结合物及其制备方法和在制药中的应用
  申请人：复旦大学

  公开号：CN111484413A

  公开（公告）日：2020-08-04

  本发明属化学制药领域，涉及中草药丹参中有效成分丹参素与H 2 S/NO供体的结合物及其制备方法和在制药中的应用，尤其是在制备防治心脑血管和炎症相关疾病药物中的用途。本发明通过体外氧化应激损伤和炎症模型实验，结果显示所述的结合物能显著抑制H 2 O 2 诱导的SH‑SY5Y细胞氧化应激损伤，对损伤细胞具有明显的保护作用；能显著抑制内毒素(LPS)诱导的小鼠腹腔巨噬细胞分泌炎性介质，减少炎症诱导的一氧化氮和炎性细胞因子的释放；体内活性实验结果显示，所述的结合物对LPS诱导的小鼠腹膜炎能改善小鼠的凝血时间，明显抑制小鼠腹腔的炎性细胞因子的释放，结果表明所述化合物可用于制备防治心脑血管疾病和炎症性疾病的药物。
• 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.