(-)-verrucosin | 891182-95-9

• 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: (-)-verrucosin
• 英文别名: (-)-odoratisol C；4-[(2R,3R,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol
• CAS: 891182-95-9
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: GMXMKSFJQLFOSO-MWRFHTASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-1-(3,4-dimethoxyphenyl)-1-oxopropan-2-yl-4-methylbenzenesulfonate 、 (-)-verrucosin 在 2-叔丁基亚氨基-2-二乙基氨基-1,3-二甲基全氢-1,3,2-二氮杂磷 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  Analysis of HIF-1 inhibition by manassantin A and analogues with modified tetrahydrofuran configurations

  摘要：

  We have shown that manassantin A downregulated the HIF-1 alpha expression and inhibited the secretion of VEGF. We have also demonstrated that the 2,3-cis-3,4-trans-4,5-cis-configuration of the tetrahydrofuran is critical to the HIF-1 inhibition of manassantin A. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.071
• 作为产物：
  描述：

  (4R,5S)-5-(4-(benzyloxy)-3-methoxyphenyl)-4-methyldihydrofuran-2(3H)-one 在 palladium on activated charcoal 正丁基锂 、 三氟化硼乙醚 、 四丁基氟化铵 、 氢气 、 sodium cyanoborohydride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 6.0h， 生成 (-)-verrucosin
  参考文献：
  名称：

  立体选择性合成的四氢呋喃木脂素通过BF（3）x OEt（2）促进的环状半缩醛的还原性脱氧/环氧加成：（-）-香豆酚C，（-）-futokadsurin A，（-）-veraguensin，（+）的合成-fragransin A（2），（+）-galbelgin和（+）-talaumidin。

  摘要：

  合成2,5-二芳基-3,4-二甲基四氢呋喃木脂素，（-）-香豆酚C（1），（-）-Futokadsurin A（2），（-）-veraguensin（3），（描述了+）-fragransin A2（4），（+）-galbelgin（5）和（+）-talaumidin（6）。木酚素合成的核心是BF（3）x OEt（2）促进半缩醛9a的脱氧/表观电子化，然后立体选择性还原氧碳鎓离子中间体8a，b。

  DOI：

  10.1021/ol7016388

文献信息

• Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps
  作者：Pratap R. Jagtap、Ivana Císařová、Ullrich Jahn

  DOI：10.1039/c7ob02848b

  日期：——

  A very short three-step approach to trans,trans,trans-2,5-diaryl-3,4-dimethyltetrahydrofuran lignans is reported. The carbon skeleton is assembled in a single step based on an unprecedented tandem reaction consisting of 1,2-addition of aryllithium reagents to α,β-unsaturated aldehydes, ruthenium-catalyzed redox isomerization of the resulting alkoxides to enolates and their dimerization triggered by

  据报道，反式，反式，反式-2,5-二芳基-3,4-二甲基四氢呋喃木脂素的非常短的三步法。碳骨架是基于空前的串联反应由一个步骤组装而成的，该串联反应由芳基锂试剂与α，β-不饱和醛的1,2-加成反应，钌催化的所得醇盐氧化还原异构化为烯醇化物以及它们的二聚反应引发。电子氧化。形成的2，3-二烷基-1，4-二酮具有中等至良好的d / l-非对映选择性，并通过还原和非对映选择性环醚化转化为目标四氢呋喃木脂素。
• Effect of the Benzylic Structure of Lignan on Antioxidant Activity
  作者：Satoshi YAMAUCHI、Takuya SUGAHARA、Junko MATSUGI、Tatsushi SOMEYA、Toshiya MASUDA、Taro KISHIDA、Koichi AKIYAMA、Masafumi MARUYAMA

  DOI：10.1271/bbb.70275

  日期：2007.9.23

  The effect of the benzylic structure of lignan on antioxidant activity was evaluated. Secoisolariciresinol (1) and 3,4-bis(4-hydroxy-3-methoxybenzyl)tetrahydrofuran (2), which have two secondary benzylic positions without oxygen, showed the highest antioxidant activity. Optically active verrucosin (4) was synthesized for the first time in this experiment.

  评估了木酚类化合物苄基结构对抗氧化活性的影响。没有氧的两个二级苄位的次羟基瑞士素 (1) 和3,4-双(4-羟基-3-甲氧基苄基)四氢呋喃 (2) 显示出最高的抗氧化活性。本实验中首次合成了具有光学活性的疣酮 (4)。
• [EN] MANASSANTIN COMPOUNDS AND METHODS OF MAKING AND USING SAME<br/>[FR] COMPOSÉS DE MANASSANTIN ET LEURS PROCÉDÉS DE PRODUCTION ET D'UTILISATION
  申请人：UNIV DUKE

  公开号：WO2010059858A1

  公开（公告）日：2010-05-27

  Provided are manassantin compounds and methods of using the compounds. Provided are methods of treating a disease, the method comprising administering a compound according to Formula I. Further provided are pharmaceutical compositions comprising compounds according to Formula I. Also provided are methods of inhibiting HIF-1 in a cell, the methods comprising administering to the cell a compound according to Formula I.

  提供了manassantin化合物和使用该化合物的方法。提供了治疗疾病的方法，该方法包括给予符合公式I的化合物。另外提供了包含符合公式I的化合物的药物组合物。还提供了在细胞中抑制HIF-1的方法，该方法包括给予细胞符合公式I的化合物。
• Total Synthesis and Stereochemical Confirmation of 2,5-Diaryl-3,4-dimethyltetrahydrofuran Lignans: (+)-Fragransin A₂, (+)-Galbelgin, (+)-Talaumidin, (-)-Saucernetin and (-)-Verrucosin
  作者：Stephen Hanessian、Gone Reddy

  DOI：10.1055/s-2007-968019

  日期：2007.2

  A new ring closure to tetrasubstituted tetrahydrofurans from the intramolecular attack of an OMOM ether onto a benzylic mesylate proceeds through a quinonoid intermediate or by direct S N 2 displacement. The synthesis of diastereomeric biologically active natural lignans is described utilizing this general methodology.

  从 OMOM 醚分子内攻击到甲磺酸苄酯的四取代四氢呋喃的新闭环通过醌类中间体或通过直接 SN 2 置换进行。使用这种通用方法描述了非对映异构生物活性天然木脂素的合成。
• Synthesis of All Stereoisomers of 3,3′-Dimethoxy-7,7′-epoxylignane-4,4′-diol and Their Plant Growth Inhibitory Activity
  作者：Hisashi Nishiwaki、Kumiko Nakayama、Yoshihiro Shuto、Satoshi Yamauchi

  DOI：10.1021/jf4046396

  日期：2014.1.22

  All stereoisomers of 3,3'-dimethoxy-7,7'-epoxylignane-4,4'-diol were synthesized to examine the effect of stereochemistry on their plant growth inhibitory activity using lettuce and Italian ryegrass. The effect of structural modifications such as dehydroxylation, methoxylation and hydroxylation at the 9- and 9'-positions of the lignans on the activity was also studied. Most of the epoxylignanes showed higher plant growth inhibitory potency against ryegrass than against lettuce, and the inhibitory activity varied depending on the configurations of each position of the tetrahydrofuran ring (7-, 7'-, 8-, and 8'-positions of the epoxylignanes). Among the 9,9'-position-modified derivatives, the dehydroxy derivatives showed the highest potency. These results suggested that the plant growth inhibitory activity should be influenced by the structure of the epoxylignanes.