3,4-bis[(methoxycarbonyl)oxy]cinnamic acid | 861897-00-9

• 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: 3,4-bis[(methoxycarbonyl)oxy]cinnamic acid
• 英文别名: 3,4-di-O-(methoxycarbonyl)caffeic acid；(E)-3-[3,4-bis(methoxycarbonyloxy)phenyl]prop-2-enoic acid
• CAS: 861897-00-9
• 化学式: C₁₃H₁₂O₈
• 分子量: 296.233
• InChiKey: RQBXNNKOGATKEA-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,4-bis[(methoxycarbonyl)oxy]cinnamic acid 在 草酰氯 作用下， 以 甲苯 为溶剂， 反应 1.83h， 生成 (E)-cyclohexyl 3-(3,4-dihydroxyphenyl)acrylate
  参考文献：
  名称：

  Radical scavenging activity of dicaffeoyloxycyclohexanes: Contribution of an intramolecular interaction of two caffeoyl residues

  摘要：

  Six regio- and stereoisomers of dicaffeoyloxycyclohexanes and 2,4-di-O-caffeoyl-1,6-anhydro-beta-D-glucose were synthesized as model compounds of dicaffeoylquinic acids, and their radical scavenging activity was evaluated by DPPH (2,2-diphenyl-1-picrylhydrazyl) and ABTS (2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) diammonium salt) radical scavenging tests. Both DPPH and ABTS radical scavenging reactions of these compounds consisted of two different steps. In the first step, catechol moieties of the caffeoyl residues were rapidly converted to o-quinone structures and no significant difference in the reactivity was observed among the tested compounds. In the second step, however, the rate of the reaction increased as the intramolecular distance of the two caffeoyl residues decreased. A novel intramolecular coupling product, which could scavenge additional radicals, was isolated from the reaction mixture of trans-1,2-dicaffeoyloxycyclohexane and DPPH radical. The result suggests that the second step of the radical scavenging reaction is arising from an intramolecular interaction between the two caffeoquinone residues to regenerate catechol structures, and that the closer their distance is, the more rapidly they react. The radical scavenging activity of natural dicaffeoylquinic acids in a biological aqueous system might also depend on the positions of caffeoyl ester groups. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.049
• 作为产物：
  描述：

  TRANS-咖啡酸 、 氯甲酸甲酯 在 TEA 作用下， 以 四氢呋喃 为溶剂， 生成 3,4-bis[(methoxycarbonyl)oxy]cinnamic acid
  参考文献：
  名称：

  某些3-芳基-2-丙酸酯的合成及其细胞毒性评估。

  摘要：

  一系列3-芳基-2-丙烯酸酯，包括肉桂酸酯，（E）-甲基/乙基3- [2-（2-（1,4-二甲氧基-5,8-二酮）萘] -2-丙烯酸酯（8ba，8bb）和合成（E）3- [2-（1,4-二羟基-9,10-二酮）蒽基] -2-丙烯酸（9aa，9ab）-甲基/乙基（9aa，9ab），并评估其抗肿瘤细胞毒性。发现芳基环上的邻或对二羟基官能对于肉桂酸酯的细胞毒性至关重要。化合物8ba，8bb和9aa，9ab对多种肿瘤细胞系显示出强力的细胞毒性。

  DOI：

  10.1016/s0960-894x(01)00165-2

文献信息

• Design, synthesis, and biological evaluation of chicoric acid analogs as inhibitors of HIV-1 integrase
  作者：Trevor T. Charvat、Deborah J. Lee、W. Edward Robinson、A. Richard Chamberlin

  DOI：10.1016/j.bmc.2006.02.030

  日期：2006.7

  A series of analogs of the potent HIV-1 integrase (HIV IN) inhibitor chicoric acid (CA) was designed with the intention of ameliorating some of the parent natural product's undesirable properties, in particular its toxicity, instability, and poor membrane permeability. More than 70 analogs were synthesized and assayed for three types of activity: (1) the ability to inhibit 3'-end processing and strand transfer reactions using recombinant HIV IN in vitro, (2) toxicity against the CD4+ lymphoblastoid cell line, MT2, and (3) anti-HIV activity against HIVLAI. CA analogs lacking one of the carboxyl groups of CA and with 3,4,5-trihydroxycinnamoyl sidechains in place of the caffeoyl group of CA exhibited the most potent inhibition of HIV replication and end-processing activity. Galloyl-substituted derivatives also displayed very potent in vitro and in vivo activities, in most cases exceeding the inhibitory effects of CA itself. Conversely, analogous monocarboxy caffeoyl analogs exhibited only modest inhibition, while the corresponding 3,4-dihydroxybenzoyl-substituted compounds were devoid of activity. (c) 2006 Elsevier Ltd. All rights reserved.