dodecyl (2E)-3-(3,4-dimethoxyphenyl)prop-2-enoate | 1455026-06-8

• 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: dodecyl (2E)-3-(3,4-dimethoxyphenyl)prop-2-enoate
• 英文别名: dodecyl (E)-3-(3,4-dimethoxyphenyl)prop-2-enoate
• CAS: 1455026-06-8
• 化学式: C₂₃H₃₆O₄
• 分子量: 376.536
• InChiKey: MKAHKRGPOWFCRA-BMRADRMJSA-N

物化性质

• 熔点：
  55-58 °C
• 沸点：
  486.1±30.0 °C(predicted)
• 密度：
  0.990±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  27
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 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 dodecyl (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 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.