sodium danshensu

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: sodium danshensu
• 英文别名: danshensu sodium；salvianic acid A sodium；danshensu sodium salt；sodium;4-[(2R)-2-carboxy-2-hydroxyethyl]-2-hydroxyphenolate
• 化学式: C₉H₉O₅*Na
• 分子量: 220.157
• InChiKey: ZMMKVDBZTXUHFO-DDWIOCJRSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -4.24
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  sodium danshensu 在 硫酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 R-β-(3,4-dibenzyloxyphenyl)-α-hydroxypropanoic acid
  参考文献：
  名称：

  Cytoprotective Effects Evaluation of a Novel Danshensu Derivative DEX-018 against Oxidative Stress Injury in HUVECs

  摘要：

  Ischemic heart disease (H-ID) is one of the most common cardiovascular diseases with high morbidity and mortality. Danshensu (DSS) is widely used in the treatment of coronary heart disease. In this study, the carboxy group of DSS was esterified with edaravone to synthesize the novel DSS derivative DEX-018 to achieve a synergistic protective effect and overcome the structural deficiency of DSS. The pharmacological effect of DEX-018 against tert-butyl hydrogen peroxide (t-BHP) induced oxidative damage in human umbilical vein endothelial cells (HUVECs) was evaluated. The results demonstrated that pretreatment with DEX-018 significantly increased cell viability and superoxide dismutase (SOD) activity and decreased the lactate dehydrogenase (LDH) leakage rate, malondialdehyde (MDA) level and intracellular reactive oxygen species (ROS) level. In addition, DEX-018 inhibited cell apoptosis and reversed the expression of apoptosis-related proteins (BcI-2, Bax, and caspase-3) in HUVECs stimulated by t-BHP Further study on the mechanism of DEX-018 revealed that the expression of p-Akt and p-extracellularsignal-regulated kinase 1/2 (ERK1/2) was increased, which suggested that DEX-018 may protect HUVECs against t-BHP induced oxidative injury viu the Akt and ERK1/2 signaling pathways. To further validate the correlation, CCK8 was used to detect cell viability after treatment with DEX-018 plus Akt inhibitor (MK2206) and phosphadylinositol 3-kinase (P13K) inhibitor (LY294002). Compared with DEX-018 alone, MK2206 or LY294002 significantly decreased cell viability of HUVECs, indicating that the protective effect of DEX-018 against t-BHP induced oxidative injury was significantly weakened. It was further verified that the antioxidant and anti-apoptotic effects of DEX-018 were partly related to the PI3K Akt signaling pathway.

  DOI：

  10.1248/bpb.b19-00878
• 作为产物：
  描述：

  N-乙酰-D-酪氨酸 在 盐酸 、 aluminum (III) chloride 、 双氧水 、 sodium hydroxide 、 sodium nitrite 作用下， 以 水 、 硝基苯 为溶剂， 反应 33.5h， 生成 sodium danshensu
  参考文献：
  名称：

  一种D-酪氨酸的不对称合成方法

  摘要：

  本发明提供一种D‑酪氨酸的不对称合成方法，包括如下步骤：首先对羟基苯甲醛和乙酰甘氨酸发生缩合反应后水解或醇解开环得到脱氢氨基酸或酯；然后利用铑催化不对称氢化后水解得到关键中间体D‑酪氨酸。本发明全过程无需复杂分离步骤，制备工艺简单，无需过层析柱，而且利用铑催化不对称氢化技术可进一步减少反应步骤，降低生产成本，非常适合工业化批量生产。

  公开号：

  CN103724217B

文献信息

• Synthesis and Biological Evaluation of Danshensu and Tetramethylpyrazine Conjugates as Cardioprotective Agents
  作者：Yingfei Wang、Xiaojing Zhang、Changjiang Xu、Gaoxiao Zhang、Zaijun Zhang、Pei Yu、Luchen Shan、Yewei Sun、Yuqiang Wang

  DOI：10.1248/cpb.c16-00839

  日期：——

  efficacy and improve their drugability, in this work, we designed new DSS and TMP conjugates. Their water solubility and protective effects were studied in vitro and in experimental animal models. The new compounds demonstrated higher activities than the positive control agents acetylated danshensu and tetramethylpyrazine conjugate (ADTM) and salvianolic acid B (SAB) in preventing cells from oxidative insult

  心肌缺血是世界范围内猝死的主要原因。包括丹参素（DSS）和四甲基吡嗪（TMP）在内的许多中药活性成分已被广泛用于治疗心肌缺血。为了提高其治疗效果并改善其可药物性，在这项工作中，我们设计了新的DSS和TMP结合物。在体外和实验动物模型中研究了它们的水溶性和保护作用。与防止乙酰氧化丹参素和四甲基吡嗪共轭物（ADTM）和丹酚酸B（SAB）的阳性对照剂相比，新化合物在阻止细胞氧化损伤方面具有更高的活性。在这些新化合物中，带有两个甘氨酸部分的14更易溶于水。此外，化合物14在防止细胞氧化损伤方面更有效，效力分别是ADTM和SAB的至少10倍和20倍。化合物14的保护作用可以归因于其抗自由基活性和抗凋亡活性。这些结果表明，化合物14是用于治疗心肌缺血的有希望的候选物。
• Pyrazine derivative, and preparation method and medical use thereof
  申请人：GUANGZHOU MAGPIE PHARMACEUTICALS CO., LTD.

  公开号：US20190276413A1

  公开（公告）日：2019-09-12

  The present invention relates to a pyrazine derivative, and preparation method and medical use thereof. The pyrazine derivative can remove free radicals and suppress calcium overload and has cytoprotective effects, and can be used for the prevention and treatment of cardiovascular and cerebrovascular diseases, neurodegenerative diseases and other related diseases.

  这项发明涉及一种吡嗪衍生物，以及其制备方法和医药用途。该吡嗪衍生物可以清除自由基、抑制钙超载，具有细胞保护作用，可用于预防和治疗心血管和脑血管疾病、神经退行性疾病和其他相关疾病。
• Synthesis of Novel Danshensu Alkamine Derivatives as Potential Anti-Myocardial Ischemia Agents
  作者：Jing-Jing Shu、Chuan Zhang、Ting-Fang Wang、Hao Zou、Lei Jin、Wei-Ying Gu、Li-Chao Zhang

  DOI：10.14233/ajchem.2014.16676

  日期：——

  Ten novel danshensu alkamine derivatives were synthesized and the preliminary biological activity of these complexes were investigated. The bioassay results indicated that some of derivatives exhibit significant activities on protecting hypoxic H9C2 cardiomyocytes.

  合成了十种新型的丹参素烷基胺衍生物，并初步探究了这些化合物的生物活性。生物测试结果表明，部分衍生物对保护缺氧H9C2心肌细胞显示出显著活性。
• Synthesis of (+)-salvianolic acid A from sodium Danshensu
  作者：Kai Xu、Hao Liu、Delong Liu、Cheng Sheng、Jiefeng Shen、Wanbin Zhang

  DOI：10.1016/j.tet.2018.08.044

  日期：2018.10

  (+)-Salvianolic acid A, one of the most active components in the traditional Chinese medicine Danshen, has been synthesized over 10 steps in 6.5% overall yield. Starting from inexpensive ortho-vanillin and sodium Danshensu (synthesized via asymmetric catalysis in our group), the process consists of the following: A Wittig reaction that gives the desire product with absolute E-configuration, a demethylation

  （+）-丹酚酸A是传统中药丹参中活性最高的成分之一，已通过10步合成，总收率为6.5％。从廉价的原香草醛和丹参素钠（在我们的小组中通过不对称催化合成）开始，该过程包括以下内容：Wittig反应可得到具有绝对E-构型的所需产物，AlCl 3脱甲基反应的产率令人满意，以及对烯丙基基团进行实际的脱保护以提供最终产物（+）-丹酚酸A。当前的合成技术具有使用廉价的起始原料，反应条件温和的优势，并且具有用于大规模合成的潜力。
• Formal total synthesis of salvianolic acid N
  作者：Kong Wu、Zhong Pao Xie、Dong-Mei Cui、Chen Zhang

  DOI：10.1039/c7ob03025h

  日期：——

  An efficient synthetic pathway for the total synthesis of salvianolic acid N has been reported. The key reaction steps, the Wittig reaction for Z-stereoselectivity and an intramolecular cyclization for a seven membered ring skeleton, have been optimized to improve the synthetic feasibility and provide the best conditions in terms of yield. Moreover, a notable reaction is the reaction of the deprotected

  已经报道了丹酚酸N全合成的有效合成途径。已经优化了关键反应步骤，即Z-立体选择性的Wittig反应和七元环骨架的分子内环化反应，以提高合成的可行性并提供最佳的收率条件。此外，值得注意的反应是脱保护的烯丙基与Pd催化剂的反应。从3,4-二甲氧基苯甲醛开始，分11步获得丹酚酸N的总收率提高了11％。