(8S,8'S)-4-hydroxy-3',4'-dimethoxylignano-9,9'-lactone

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: (8S,8'S)-4-hydroxy-3',4'-dimethoxylignano-9,9'-lactone
• 英文别名: (3S,4S)-3-benzyl-4-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: ZSKMPIQKIFCKLW-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (R)-4-benzyl-3-(3-(3,4-dimethoxyphenyl)propanoyl)-oxazolidin-2-one 在 四氧化锇 、 锂硼氢 、 N-甲基吗啉氧化物 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 叔丁醇 为溶剂， 反应 75.0h， 生成 (8S,8'S)-4-hydroxy-3',4'-dimethoxylignano-9,9'-lactone
  参考文献：
  名称：

  Discovery of stereospecific cytotoxicity of (8R,8′R)-trans-arctigenin against insect cells and structure-activity relationship on aromatic ring

  摘要：

  One of the arctigenin stereoisomers, (8R,8'R)-trans-form 1, showed stereospecific cytotoxicity against insect cells, Sf9 and NIAS-AeAl-2 cells. By the comparison with other stereoisomers, the most importance of the 8'R stereochemistry for the higher activities was clarified. On the other hand, the wider range of activity level among stereoisomers against cancer cells, HL-60, was not observed. The structure-activity relationship research using derivatives bearing (8R,8'R)-trans-form was performed to show the same level of activities of 3-iodo, 4-iodo, and 3,4-methylenedioxy derivatives 28, 29, and 36 as (8R,8'R)-trans-arctigenin 1. In the examination of thiono derivatives, 4-iodo thiono and 3,4-methylenedioxy thiono derivatives 66, 67 showed similar level of activities to that of (8R,8'R)-trans-arctigenin 1. The expression of ribosomal 28S rRNA gene of Sf9 cells was increased by (8R,8'R)-trans-arctigenin 1, whereas a degradation of DNA was not observed.

  DOI：

  10.1016/j.bmcl.2020.127191

文献信息

• (−)-Arctigenin as a Lead Structure for Inhibitors of Human Immunodeficiency Virus Type-1 Integrase
  作者：Eckart Eich、Heinz Pertz、Macki Kaloga、Jutta Schulz、Mark R. Fesen、Abhijit Mazumder、Yves Pommier

  DOI：10.1021/jm950387u

  日期：1996.1.1

  congener with two catechol substructures (7) was found to be the most active compound in this study. 7 was also a potent inhibitor of the "disintegration" reaction which models the reversal of the strand transfer reaction. The inhibitory activity of 7 with the core enzyme fragment consisting of amino acids 50-212 suggests that the binding site of 7 resides in the catalytic domain.

  发现天然二苄基丁内酯型木质素（-）-arctigenin（2）是一种人类免疫缺陷病毒1型（HIV-1）在感染的人类细胞系统中复制的抑制剂，可抑制前病毒DNA整合到细胞DNA基因组中。在本研究中，2用纯化的HIV-1整合酶进行了测试，发现在裂解（3'-加工）和整合（链转移）测定中无活性。然而，以儿茶酚亚结构为特征的半合成3-O-去甲基化同源物9在两种测定中均表现出显着的活性。用30种天然（1-6），半合成（7-21）和合成（37-43、45、46）的木脂素进行结构-活性关系研究表明，（1）内酯部分至关重要，因为带有丁烷-1的化合物，4-二醇或四氢呋喃的亚结构以及木脂酰胺类似物缺乏活性，（2）酚羟基的数量和排列对于木质素的活性很重要。在本研究中，发现具有两个邻苯二酚亚结构的同类物（7）是活性最高的化合物。7也是“崩解”反应的有效抑制剂，其模拟了链转移反应的逆转。7对由氨基酸50-212组成的核
• Discovery of stereospecific cytotoxicity of (8R,8′R)-trans-arctigenin against insect cells and structure-activity relationship on aromatic ring
  作者：Satoshi Yamauchi、Asuka Nishimoto、Hisashi Nishiwaki、Kosuke Nishi、Takuya Sugahara

  DOI：10.1016/j.bmcl.2020.127191

  日期：2020.7

  One of the arctigenin stereoisomers, (8R,8'R)-trans-form 1, showed stereospecific cytotoxicity against insect cells, Sf9 and NIAS-AeAl-2 cells. By the comparison with other stereoisomers, the most importance of the 8'R stereochemistry for the higher activities was clarified. On the other hand, the wider range of activity level among stereoisomers against cancer cells, HL-60, was not observed. The structure-activity relationship research using derivatives bearing (8R,8'R)-trans-form was performed to show the same level of activities of 3-iodo, 4-iodo, and 3,4-methylenedioxy derivatives 28, 29, and 36 as (8R,8'R)-trans-arctigenin 1. In the examination of thiono derivatives, 4-iodo thiono and 3,4-methylenedioxy thiono derivatives 66, 67 showed similar level of activities to that of (8R,8'R)-trans-arctigenin 1. The expression of ribosomal 28S rRNA gene of Sf9 cells was increased by (8R,8'R)-trans-arctigenin 1, whereas a degradation of DNA was not observed.