23-O-(4,4’-dimethoxytriphenylmethyl)silibinin | 1326308-16-0

• 分子结构分类: 有机化合物
• 英文名称: 23-O-(4,4’-dimethoxytriphenylmethyl)silibinin
• 英文别名: 23-O-(4,4'-dimethoxytriphenylmethyl)-silybin
• CAS: 1326308-16-0
• 化学式: C₄₆H₄₀O₁₂
• 分子量: 784.816
• InChiKey: ABPQBPTYLMVNNN-DTJNQQROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  58.0
• 可旋转键数：
  11.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  162.6
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  23-O-(4,4’-dimethoxytriphenylmethyl)silibinin 在 吡啶 、 甲酸 、 叠氮磷酸二苯酯 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 3,5,7-O-triacetyl-23-azide-silybin
  参考文献：
  名称：

  水飞蓟宾和2,3-脱氢水飞蓟宾的新型C-23改性：抗氧化性能的合成和初步评估

  摘要：

  水飞蓟宾是水飞蓟素的主要黄酮木脂素，它具有多种生物学效应，通常归因于其抗氧化性能。本文中，我们将描述一种有效的合成策略，以使用以下方法获得各种新的和更水溶性的水飞蓟宾和2,3-脱氢水飞蓟宾（DHS）衍生物，其中23-羟基被转化为硫酸盐，磷酸二酯或胺基解决方案阶段的方法。此外，开发和优化了一种新的，高效的从水飞蓟宾制备DHS的方法。 在体内细胞模型中评估了新化合物的抗氧化性能，它们显示出的抗氧化活性与水飞蓟宾和DHS相当或更高，能够防止H 2 O 2诱导的细胞内活性氧（ROS）生成。大多数衍生物还表现出更好的亲水性，同时保留了水飞蓟宾的生物活性，它们可能会拓宽此类天然化合物的体内应用范围。

  DOI：

  10.1016/j.bmcl.2011.06.049
• 作为产物：
  描述：

  水飞蓟素A,B 、 三苯基氯甲烷 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到23-O-(4,4’-dimethoxytriphenylmethyl)silibinin
  参考文献：
  名称：

  水飞蓟宾和2,3-脱氢水飞蓟宾的新型C-23改性：抗氧化性能的合成和初步评估

  摘要：

  水飞蓟宾是水飞蓟素的主要黄酮木脂素，它具有多种生物学效应，通常归因于其抗氧化性能。本文中，我们将描述一种有效的合成策略，以使用以下方法获得各种新的和更水溶性的水飞蓟宾和2,3-脱氢水飞蓟宾（DHS）衍生物，其中23-羟基被转化为硫酸盐，磷酸二酯或胺基解决方案阶段的方法。此外，开发和优化了一种新的，高效的从水飞蓟宾制备DHS的方法。 在体内细胞模型中评估了新化合物的抗氧化性能，它们显示出的抗氧化活性与水飞蓟宾和DHS相当或更高，能够防止H 2 O 2诱导的细胞内活性氧（ROS）生成。大多数衍生物还表现出更好的亲水性，同时保留了水飞蓟宾的生物活性，它们可能会拓宽此类天然化合物的体内应用范围。

  DOI：

  10.1016/j.bmcl.2011.06.049

文献信息

• New Silybin Scaffold for Chemical Diversification: Synthesis of Novel 23-Phosphodiester Silybin Conjugates
  作者：Giovanni Di Fabio、Armando Zarrelli、Valeria Romanucci、Marina Greca、Lorenzo De Napoli、Lucio Previtera

  DOI：10.1055/s-0032-1317688

  日期：——

  Silybin is the major component (ca. 30%) of the silymarin complex extracted from the seeds of Silybum marianum, with multiple biological activities operating at various cell levels. As an ongoing effort toward the exploitation of natural products as scaffolds for chemical diversification at readily accessible positions, we present here an efficient synthetic procedure to obtain new 23-phosphodiester silybin conjugates with different labels. A key point in our approach is the new 3,5,7,20-tetra-O-acetylsilybin-23-phosphoramidite, useful for a variety of derivatizations following a reliable and well-known chemistry. The feasibility of the procedure has been demonstrated by preparing new 23-silybin conjugates, exploiting standard phosphoramidite chemistry.
• Regioselective synthesis of 7-O-esters of the flavonolignan silibinin and SARs lead to compounds with overadditive neuroprotective effects
  作者：Simon Schramm、Guozheng Huang、Sandra Gunesch、Florian Lang、Judit Roa、Petra Högger、Raimon Sabaté、Pamela Maher、Michael Decker

  DOI：10.1016/j.ejmech.2018.01.036

  日期：2018.2

  A series of neuroprotective hybrid compounds was synthesized by conjugation of the flavonolignan silibinin with natural phenolic acids, such as ferulic, cinnamic and syringic acid. Selective 7-O-esterfication without protection groups was achieved by applying the respective acyl chlorides. Sixteen compounds were obtained and SARs were established by evaluating antioxidative properties in the physicochemical FRAP assay, as well as in a cell-based neuroprotection assay using murine hippocampal HT-22 cells. Despite weak activities in the FRAP assay, esters of the alpha,beta-unsaturated acids showed pronounced overadditive effects at low concentrations greatly exceeding the effects of equimolar mixtures of silibinin and the respective acids in the neuroprotection assay. Cinnamic and ferulic acid esters (5a and 6a) also showed overadditive effects regarding inhibition of microglial activation, PC12 cell differentiation, in vitro ischemia as well as anti-aggregating abilities against A beta 42 peptide and tau protein. Remarkably, the esters of ferulic acid with silybin A and silybin B (11a and 11b) showed a moderate but significant difference in both neuroprotection and in their anti-aggregating capacities. The results demonstrate that non-toxic natural antioxidants can be regioselectively connected as esters with medium-term stability exhibiting very pronounced overadditive effects in a portfolio of biological assays. (C) 2018 Elsevier Masson SAS. All rights reserved.