hexadecyl (2E)-3-(3,4-dimethoxyphenyl)prop-2-enoate | 1269765-62-9

• 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: hexadecyl (2E)-3-(3,4-dimethoxyphenyl)prop-2-enoate
• 英文别名: trans-hexadecyl 3-(3,4-dimethoxyphenyl)propenoate；hexadecyl (E)-3-(3,4-dimethoxyphenyl)prop-2-enoate
• CAS: 1269765-62-9
• 化学式: C₂₇H₄₄O₄
• 分子量: 432.644
• InChiKey: SUBCTRJVEYTGLK-XUTLUUPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  31
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  3,4-二甲氧基苯甲醛 在 氯化亚砜 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 8.0h， 生成 hexadecyl (2E)-3-(3,4-dimethoxyphenyl)prop-2-enoate
  参考文献：
  名称：

  Synthesis and leishmanicidal activity of cinnamic acid esters: structure–activity relationship

  摘要：

  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.

  DOI：

  10.1007/s00044-013-0741-y

文献信息

• Synthesis and antioxidant activity of long chain alkyl hydroxycinnamates
  作者：Jose C.J.M.D.S. Menezes、Shrivallabh P. Kamat、Jose A.S. Cavaleiro、Alexandra Gaspar、Jorge Garrido、Fernanda Borges

  DOI：10.1016/j.ejmech.2010.12.016

  日期：2011.2

  Long chain alkyl hydroxycinnamates (8–21) were synthesized from the corresponding half esters of malonic acid (5–7) and benzaldehyde derivatives by Knoevenagel condensation. The total antioxidant capacity of these hydroxycinnamyl esters was evaluated using DPPH and ABTS assays. The observed antioxidant activity was highest for esters of caffeic acid followed by sinapic esters and ferulic esters. The

  长链烷基羟基肉桂酸酯（8 – 21）是由丙二酸的相应半酯（5 – 7）合成的）与苯甲醛衍生物经Knoevenagel缩合。使用DPPH和ABTS分析评估了这些羟基肉桂酸酯的总抗氧化能力。观察到的抗氧化剂活性最高的是咖啡酸酯，其次是芥子酸酯和阿魏酸酯。这些羟基肉桂酸酯的类药性参数也根据L​​ipinski的“五则规则”进行了评估。发现所有酯衍生物均违反了Lipinski的参数之一（cLogP> 5），即使已发现它们可溶于质子溶剂中。预测的拓扑极性表面积（TPSA）数据可以得出结论，它们可以具有良好的穿透细胞膜的能力。因此，可以提出这些新颖的亲脂性化合物作为用于应对氧化过程的潜在抗氧化剂。
• 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.