3-(3,4-methylenedioxyphenyl)-2-hydroxypropanoic acid | 949-14-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 3-(3,4-methylenedioxyphenyl)-2-hydroxypropanoic acid
• 英文别名: 3-(3,4-methylenedioxyphenyl)lactic acid；3-benzo[1,3]dioxol-5-yl-2-hydroxy-propionic acid；3-Benzo[1,3]dioxol-5-yl-2-hydroxy-propionsaeure；β-(benzo[1,3]dioxol-5-yl)-α-hydroxypropionic acid；3-(3,4-Methylendioxy-phenyl)-milchsaeure；3-(1,3-Benzodioxol-5-yl)-2-hydroxypropanoic acid
• CAS: 949-14-4
• 化学式: C₁₀H₁₀O₅
• 分子量: 210.186
• InChiKey: YXQUWVVBVQJDCK-UHFFFAOYSA-N

物化性质

• 熔点：
  101 °C
• 沸点：
  407.2±40.0 °C(Predicted)
• 密度：
  1.475±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3,4-methylenedioxyphenyl)-2-hydroxypropanoic acid 在 吗啉 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 三溴化硼 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 61.5h， 生成 迷迭香酸
  参考文献：
  名称：

  Bryophyte Constituents; 7: New Synthesis of (+)-Rosmarinic Acid and Related Compounds

  摘要：

  描述了迷迭香酸（1）及其衍生物2-4的高效快捷合成方法，广泛采用了烯丙基保护基团用于羧酸和酚类构建单元。通过化学酶促拆分其苯基乳酸前体，获得了(+)-(R)-迷迭香酸。

  DOI：

  10.1055/s-1996-4289
• 作为产物：
  描述：

  (Z)-3-(benzo[d][1,3]dioxol-5-yl)-2-hydroxyacrylic acid 在 盐酸 、 汞 、 锌 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以81%的产率得到3-(3,4-methylenedioxyphenyl)-2-hydroxypropanoic acid
  参考文献：
  名称：

  A Modified Synthesis of (±)-β-Aryllactic acids

  摘要：

  据报道，丹参中活性成分的外消旋形式，即（±）-ß-(3,4-二羟基苯基)乳酸[(±)-3-(3,4-二羟基苯基)-2-羟基丙酸]及其七种外消旋衍生物已成功合成。

  DOI：

  10.1055/s-1992-26228

文献信息

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

  公开号：US20090131677A1

  公开（公告）日：2009-05-21

  The present invention relates to a compound of the formula (I), wherein R 1 , R 2 and R 3 are each independently selected from H, OH, F, Cl, Br, methoxy and ethoxy; or alternatively, R 1 and R 2 together form —OCH 2 O—, R 3 is selected from H, OH, methoxy, ethoxy and halogens; R 4 is OH or acyloxy; R 5 is cycloalkoxyl, amino and substituted amino, and when R 5 is selected from amino, at least one of R 1 , R 2 and R 3 is not H. The present invention further relates to a process for synthesizing a compound of the formula (I), and use of the compound of the formula (I) in the manufacture of a medicament for the prevention or treatment of cardiovascular or cerebrovascular diseases.

  本发明涉及公式（I）的化合物，其中R1、R2和R3各自独立地选自H、OH、F、Cl、Br、甲氧基和乙氧基；或者，R1和R2一起形成-OCH2O-，R3选自H、OH、甲氧基、乙氧基和卤素；R4为OH或酰氧基；R5为环烷氧基、氨基和取代氨基，当R5选自氨基时，至少有R1、R2和R3中的一个不是H。本发明还涉及合成公式（I）化合物的方法，以及使用公式（I）化合物制造用于预防或治疗心血管或脑血管疾病的药物。
• DEPSIPEPTIDE DERIVATIVE, PRODUCTION THEREOF AND USE THEREOF
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0634408A1

  公开（公告）日：1995-01-18

  A compound represented by general formula (I) or a salt thereof, excellent in parasiticidal activity as an enthelmintic for animal and man, wherein A represents benzyl which is appropriately substituted or phenyl which may be appropriately substituted; Aa represents benzyl or phenyl each of which may be appropriately substituted; B and D represent each lower alkyl; and C represents hydrogen or lower alkyl.

  通式（I）所代表的化合物或其盐，作为动物和人的驱虫药，具有优异的杀寄生虫活性，其中 A 代表被适当取代的苄基或可被适当取代的苯基；Aa 代表苄基或苯基，其中每个都可被适当取代；B 和 D 分别代表低级烷基；C 代表氢或低级烷基。
• Substituted beta-phenyl-alpha-hydroxy propanoic acid, synthesis method and use thereof
  申请人：Northwest University

  公开号：EP2514739A1

  公开（公告）日：2012-10-24

  The present invention relates to a compound of the formula (I), wherein R1, R2 and R3 are each independently selected from H, OH, F, Cl, Br, methoxy and ethoxy; or alternatively, R1 and R2 together form -OCH2O-, R3 is selected from H, OH, methoxy, ethoxy and halogens; R4 is OH or acyloxy; R5 is cycloalkoxyl, amino and substituted amino, and when R5 is selected from amino, at least one of R1, R2 and R3 is not H. The present invention further relates to a process for synthesizing a compound of the formula (I), and use of the compound of the formula (I) in the manufacture of a medicament for the prevention or treatment of cardiovascular or cerebrovascular diseases.

  本发明涉及一种式(I)化合物，其中R1、R2和R3各自独立地选自H、OH、F、Cl、Br、甲氧基和乙氧基；或者，R1和R2一起形成-OCH2O-，R3选自H、OH、甲氧基、乙氧基和卤素；R4是OH或酰氧基；R5是环烷氧基、氨基和取代氨基，当R5选自氨基时，R1、R2和R3中至少有一个不是H。本发明进一步涉及一种合成式（I）化合物的工艺，以及式（I）化合物在制造预防或治疗心脑血管疾病的药物中的用途。
• 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
• 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.