(1R,2S)-cyclohexane-1,2-diyl (2E,2'E)-bis(3-(3,4-dihydroxyphenyl)acrylate)

• 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: (1R,2S)-cyclohexane-1,2-diyl (2E,2'E)-bis(3-(3,4-dihydroxyphenyl)acrylate)
• 英文别名: cis-1,2-dicaffeoyloxycyclohexane；[(1S,2R)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxycyclohexyl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• 化学式: C₂₄H₂₄O₈
• 分子量: 440.45
• InChiKey: ABRIKWKVYABQBU-PUGJRYCPSA-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：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  TRANS-咖啡酸 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 2.0h， 生成 (1R,2S)-cyclohexane-1,2-diyl (2E,2'E)-bis(3-(3,4-dihydroxyphenyl)acrylate)
  参考文献：
  名称：

  通过菊苣酸的构效关系研究检测肉毒杆菌神经毒素 A 蛋白酶的 α-外位点抑制剂

  摘要：

  肉毒杆菌神经毒素 (BoNT) 是已知毒性最强的物质之一，目前尚无针对神经元内 BoNT 中毒的有效治疗方法。菊苣酸 (ChA) 先前被报道为一种 BoNT/A 抑制剂，可与该酶的 α-外部位点结合。在此，我们报告了一系列 ChA 衍生物的合成和构效关系 (SAR)，揭示了 ChA 和 BoNT/A 之间的重要结合相互作用。此外，还发现了几种基于 ChA 的抑制剂，其对抗 BoNT/A 的效力有所提高。

  DOI：

  10.1016/j.bmcl.2017.10.021

文献信息

• Radical scavenging activity of dicaffeoyloxycyclohexanes: Contribution of an intramolecular interaction of two caffeoyl residues
  作者：Shizuka Saito、Satoshi Kurakane、Miyuki Seki、Eiji Takai、Takanori Kasai、Jun Kawabata

  DOI：10.1016/j.bmc.2005.04.049

  日期：2005.7

  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.
• Examination of α-exosite inhibitors against Botulinum neurotoxin A protease through structure-activity relationship studies of chicoric acid
  作者：Song Xue、Hajime Seki、Marek Remes、Peter Šilhár、Kim Janda

  DOI：10.1016/j.bmcl.2017.10.021

  日期：2017.11

  Chicoric acid (ChA) was previously reported as a BoNT/A inhibitor that binds to the enzyme’s α-exosite. Herein, we report the synthesis and structure-activity relationships (SARs) of a series of ChA derivatives, which revealed essential binding interactions between ChA and BoNT/A. Moreover, several ChA-based inhibitors with improved potency against the BoNT/A were discovered.

  肉毒杆菌神经毒素 (BoNT) 是已知毒性最强的物质之一，目前尚无针对神经元内 BoNT 中毒的有效治疗方法。菊苣酸 (ChA) 先前被报道为一种 BoNT/A 抑制剂，可与该酶的 α-外部位点结合。在此，我们报告了一系列 ChA 衍生物的合成和构效关系 (SAR)，揭示了 ChA 和 BoNT/A 之间的重要结合相互作用。此外，还发现了几种基于 ChA 的抑制剂，其对抗 BoNT/A 的效力有所提高。