3-(4-methoxymethoxyphenyl)propyl 3-(3,4-dimethoxymethoxyphenyl)propanoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-methoxymethoxyphenyl)propyl 3-(3,4-dimethoxymethoxyphenyl)propanoate
• 英文别名: 3-[4-(Methoxymethoxy)phenyl]propyl 3-[3,4-bis(methoxymethoxy)phenyl]propanoate
• 化学式: C₂₄H₃₂O₈
• 分子量: 448.513
• InChiKey: JDVUIYGCSPSNNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  32
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (E)-3-(3,4-bis(methoxymethoxy)phenyl)acrylic acid 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 3-(4-methoxymethoxyphenyl)propyl 3-(3,4-dimethoxymethoxyphenyl)propanoate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Natural Ester Sintenin and Its Synthetic Analogues

  摘要：

  Synthesis of 3-(3,4-dimethoxyphenyl)propyl-3-(3,4-dimethoxyphenyl) propanoate (18), a cytotoxic natural ester, was carried out by a convenient synthetic path with a total yield of 49%. Sixteen of its analogues (19-34) were also prepared. Seventeen unsaturated derivatives of 18, compounds 1-17, were also synthesized to examine the structure-activity relationship of this type of ester. All of the synthetic compounds were passed through the cytotoxicity screenings on human tumor cell lines, such as PC-3, Hela, A549, BEL7404, CNE, and KB. Some of the esters exhibited moderate inhibitory effects on these tumor cell lines. The phenolic derivatives exhibited the highest cytotoxicity among these derivatives, while the unsaturated esters were more cytotoxic than the saturated analogues. Some of the compounds also exhibited inhibition on a-glucosidase.

  DOI：

  10.1021/np0496441

文献信息

• Synthesis and Biological Evaluation of a Natural Ester Sintenin and Its Synthetic Analogues
  作者：Li Hong Hu、Hong Bin Zou、Jing Xu Gong、Hai Bo Li、Lei Xiang Yang、Wei Cheng、Chang Xin Zhou、Hua Bai、Françoise Guéritte、Yu Zhao

  DOI：10.1021/np0496441

  日期：2005.3.1

  Synthesis of 3-(3,4-dimethoxyphenyl)propyl-3-(3,4-dimethoxyphenyl) propanoate (18), a cytotoxic natural ester, was carried out by a convenient synthetic path with a total yield of 49%. Sixteen of its analogues (19-34) were also prepared. Seventeen unsaturated derivatives of 18, compounds 1-17, were also synthesized to examine the structure-activity relationship of this type of ester. All of the synthetic compounds were passed through the cytotoxicity screenings on human tumor cell lines, such as PC-3, Hela, A549, BEL7404, CNE, and KB. Some of the esters exhibited moderate inhibitory effects on these tumor cell lines. The phenolic derivatives exhibited the highest cytotoxicity among these derivatives, while the unsaturated esters were more cytotoxic than the saturated analogues. Some of the compounds also exhibited inhibition on a-glucosidase.