CABzA | 100668-10-8

• 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: CABzA
• 英文别名: N-benzyl-3-(3,4-dihydroxyphenyl)prop-2-enamide
• CAS: 100668-10-8
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: JBDQTGJGXFAHIQ-UHFFFAOYSA-N

物化性质

• 熔点：
  165 °C
• 沸点：
  570.2±50.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  咖啡酸 、 苄胺 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 生成 CABzA
  参考文献：
  名称：

  Host–guest complexation of antioxidative caffeic and ferulic acid amides with a functionalized cyclophane

  摘要：

  我们通过 1H NMR 研究了阿魏酸和咖啡酸的苄基和苯乙基酰胺在氯仿和乙腈中的主-客复合物；反主是一种环烷，它在大环框架中集成了四个亚苯基环、氨基和酰胺基团，并带有四个下垂的醋酸甲酯臂。CAPE 是最著名的天然抗氧化剂之一，我们也对其进行了比较研究。在所研究的客体中，阿魏酸苄基酰胺在氯仿中形成的主-客体复合物显示出核磁共振偏移。络合分两步进行，形成常数 K 1 = [HG]/[H][G] = 6 M-1 和 β 2 = [HG2]/[H][G]2 = 87 M-2 。两个客体分子通过两个氢键（NH（主酰胺）--O=C（客体酰胺）和 C=O（主酯）--HO（客体苯酚））结合在主分子的大环框架表面。后一个氢键可保护络合物中捕获的客体分子的生物活性位点（即苯酚羟基）免受不良氧化。只有阿魏酸苄基酰胺在氯仿中才能观察到这一特征；环烷酯与这种酰胺的相互作用与其他羟基肉桂酸衍生物不同。

  DOI：

  10.1007/s10847-012-0134-8

文献信息

• Synthesis and structure–activity relationship analysis of caffeic acid amides as selective matrix metalloproteinase inhibitors
  作者：Zhi-Hao Shi、Nian-Guang Li、Qian-Ping Shi、Hao Tang、Yu-Ping Tang、Wei Li、Lian Yin、Jian-Ping Yang、Jin-Ao Duan

  DOI：10.1016/j.bmcl.2013.01.027

  日期：2013.3

  Four series of acid amides were synthesized, and through measurement using a fluorogenic substrate assay with human recombinant MMP-1, MMP-2 and MMP-9, compound 3f showed considerable inhibitory activities against MMP-2, MMP-9 and the best selectivity over MMP-1. Preliminary structure–activity relationship analysis indicated that caffeic acid amides with electron-donating groups at para-position of

  合成了四个系列的酰胺，并通过使用荧光底物测定法与人重组MMP-1，MMP-2和MMP-9进行测量，化合物3f对MMP-2，MMP-9表现出相当大的抑制活性，并且选择性优于MMP-1。初步的结构-活性关系分析表明，在氨基苯基对位具有供电子基团的咖啡酰胺比具有吸电子基团的酰胺具有更好的抑制活性和选择性，并且在咖啡酰基中相邻的二羟基的存在非常多。对于MMP-2和MMP-9抑制活性很重要。
• Electrochemical Oxidation of Caffeic and Ferulic Acid Derivatives in Aprotic Medium
  作者：Magali Salas-Reyes、Javier Hernández、Zaira Domínguez、Felipe J. González、Pablo D. Astudillo、Rosa Elena Navarro、Evelin Martínez-Benavidez、Carlos Velázquez-Contreras、Samuel Cruz-Sánchez

  DOI：10.1590/s0103-50532011000400012

  日期：——

  We studied the electrochemical behaviour as a function of the structure of a series of caffeic and ferulic acids derivatives as well as their corresponding redox moieties catechol and guaiacol by cyclic voltammetry. Results revealed that the medium is key for changes in the oxidation mechanism of guaiacol and ferulic acid. Electrochemical oxidation of the ferulic acid amide derivatives revealed that the nitrogen atom plays an important role in the derivatization of the electrode surface. In addition, radical scavenging activity of the compounds evaluated through the percentage of inhibition of the 2,2'-diphenyl-1-picrylhidrazyl radical showed a good relationship with the oxidation potentials.
• Host–guest complexation of antioxidative caffeic and ferulic acid amides with a functionalized cyclophane
  作者：Claudia Virués、Zaira Domínguez、Magali Salas、Rosa Elena Navarro、Enrique F. Velázquez、Samuel Cruz、Javier Hernández、Motomichi Inoue

  DOI：10.1007/s10847-012-0134-8

  日期：2012.12

  Host−guest complexation has been studied by 1H NMR on the benzyl and phenethyl amides of ferulic and caffeic acids as the guests in chloroform and acetonitrile; the counter host is a cyclophane which integrates four phenylene rings, amino and amide groups in the macrocyclic framework and bears four pendant methyl acetate ester arms. CAPE, one of the best known natural antioxidants, also has been studied for comparison. Among the guests studied, ferulic acid benzyl amide shows NMR shifts due to the formation of a host−guest complex in chloroform. The complexation occurs in two steps with the formation constants K 1 = [HG]/[H][G] = 6 M−1 and β 2 = [HG2]/[H][G]2 = 87 M−2. Two guest molecules are bound on the surface of the macrocyclic framework of a host molecule by two hydrogen bonds, NH(host amide)···O=C(guest amide) and C=O(host ester)···HO(guest phenol). The latter hydrogen bond may protect the bioactive site, i.e., phenol OH, of guest molecules captured in the complex against undesirable oxidation. This feature is observed only for ferulic acid benzyl amide in chloroform; the cyclophane ester interacts with this amide, distinctively from the other hydroxycinnamic acid derivatives.

  我们通过 1H NMR 研究了阿魏酸和咖啡酸的苄基和苯乙基酰胺在氯仿和乙腈中的主-客复合物；反主是一种环烷，它在大环框架中集成了四个亚苯基环、氨基和酰胺基团，并带有四个下垂的醋酸甲酯臂。CAPE 是最著名的天然抗氧化剂之一，我们也对其进行了比较研究。在所研究的客体中，阿魏酸苄基酰胺在氯仿中形成的主-客体复合物显示出核磁共振偏移。络合分两步进行，形成常数 K 1 = [HG]/[H][G] = 6 M-1 和 β 2 = [HG2]/[H][G]2 = 87 M-2 。两个客体分子通过两个氢键（NH（主酰胺）--O=C（客体酰胺）和 C=O（主酯）--HO（客体苯酚））结合在主分子的大环框架表面。后一个氢键可保护络合物中捕获的客体分子的生物活性位点（即苯酚羟基）免受不良氧化。只有阿魏酸苄基酰胺在氯仿中才能观察到这一特征；环烷酯与这种酰胺的相互作用与其他羟基肉桂酸衍生物不同。