(E)-propyl 3-(3,4-dimethoxyphenyl)acrylate | 1455025-97-4

• 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: (E)-propyl 3-(3,4-dimethoxyphenyl)acrylate
• 英文别名: propyl (2E)-3-(3,4-dimethoxyphenyl)prop-2-enoate；propyl (E)-3-(3,4-dimethoxyphenyl)prop-2-enoate
• CAS: 1455025-97-4
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: DEPHPJWIOFCNOX-SOFGYWHQSA-N

物化性质

• 沸点：
  367.3±27.0 °C(predicted)
• 密度：
  1.081±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,4-二甲氧基肉酸酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (E)-propyl 3-(3,4-dimethoxyphenyl)acrylate
  参考文献：
  名称：

  肉桂酸酯对蘑菇酪氨酸酶的抑制作用

  摘要：

  合成了一系列取代的肉桂酸酯，并评价了其对蘑菇酪氨酸酶双酚酶活性的抑制作用。发现化合物8是最有效的抑制剂，IC50值为5.60µM。初步的结构活动关系（SAR）总结。通过Lineweaver-Burk图分析的抑制动力学表明，化合物8是抗竞争性抑制剂。

  DOI：

  10.2174/1570180811310060009

文献信息

• Synthesis and leishmanicidal activity of cinnamic acid esters: structure–activity relationship
  作者：Elver Otero、Sara M. Robledo、Santiago Díaz、Miguel Carda、Diana Muñoz、Julian Paños、Ivan D. Vélez、Wilson Cardona

  DOI：10.1007/s00044-013-0741-y

  日期：2014.3

  Several cinnamic acid esters were obtained via Fischer esterification of cinnamic acids derivatives with aliphatic alcohols. Structures of the products were elucidated by spectroscopic analysis. The synthesized compounds were evaluated for antileishmanial activity against L. (V) panamensis amastigotes and cytotoxic activity was evaluated against mammalian U-937 cells. The compounds 11, 15-17, and 23, were active against Leishmania parasite and although toxic for mammalian cells, they still are potential candidates for antileishmanial drug development. A SAR analysis indicates that first, while smaller alkyl chains lead to higher selectivity indices (10, 11 vs. 12-17); second, the degree of oxygenation is essential for activity, primarily in positions 3 and 4 (17 vs. 18-20 and 22); and third, hydroxyl groups increase both activity and cytotoxicity (14 vs. 23). On the other hand, the presence of a double bond in the side chain is crucial for cytotoxicity and leishmanicidal activity (12 vs. 21). However, further studies are required to optimize the structure of the promising molecules and to validate the in vitro activity against Leishmania demonstrated here with in vivo studies.
• Inhibitory Effects of Substituted Cinnamic Acid Esters on Mushroom Tyrosinase
  作者：Zhenghua Zhang、Jinbing Liu、Fengyan Wu、Liangzhong Zhao

  DOI：10.2174/1570180811310060009

  日期：2013.5.1

  A series of substituted cinnamic acid esters were synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. Compound 8 was found to be the most potent inhibitor with IC50 value of 5.60µM. Preliminary structure activity relationships (SARs) were concluded. The inhibition kinetics analyzed by Lineweaver–Burk plots revealed that compound 8 was anti-competitive

  合成了一系列取代的肉桂酸酯，并评价了其对蘑菇酪氨酸酶双酚酶活性的抑制作用。发现化合物8是最有效的抑制剂，IC50值为5.60µM。初步的结构活动关系（SAR）总结。通过Lineweaver-Burk图分析的抑制动力学表明，化合物8是抗竞争性抑制剂。