3,4,2',3'-tetramethoxy-trans-stilbene | 238754-86-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3,4,2',3'-tetramethoxy-trans-stilbene
• 英文别名: trans-3,4,2',3'-tetramethoxystilbene；(E)-2,3,3',4'-tetramethoxystilbene；1-[(1E)-2-(3,4-Dimethoxyphenyl)ethenyl]-2,3-dimethoxybenzene；1-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-2,3-dimethoxybenzene
• CAS: 238754-86-4
• 化学式: C₁₈H₂₀O₄
• 分子量: 300.354
• InChiKey: NDXGNBBSRNNYTQ-CSKARUKUSA-N

物化性质

• 熔点：
  110-111 °C
• 沸点：
  429.0±40.0 °C(predicted)
• 密度：
  1.117±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,4-二甲氧基苄氯 在 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 3,4,2',3'-tetramethoxy-trans-stilbene
  参考文献：
  名称：

  3,4,2′-Trimethoxy-trans-stilbene – a potent CYP1B1 inhibitor

  摘要：

  一种新型的含有3,4-二甲氧基基团的反式-苯乙烯系列化合物被设计和合成。评估了3,4-二甲氧基苯乙烯衍生物对细胞色素P450同工酶CYP1A1、CYP1B1和CYP1A2的抑制活性。3,4,2′-三甲氧基反式-苯乙烯（3,4,2′-TMS）对CYP1B1活性表现出极强的抑制作用，IC50为0.004 μM。3,4,2′-TMS在CYP1B1与CYP1A1之间表现出90倍的选择性，在CYP1B1与CYP1A2之间表现出830倍的选择性。然而，3,4,2′,4′-四甲氧基反式-苯乙烯似乎是对CYP1B1和CYP1A1最具选择性的抑制剂，对CYP1A2表现出非常低的亲和力。为了说明苯乙烯衍生物特定的亲和力决定因素，补充实验研究和计算方法被用来解释结构特征如何影响与CYP1A2和CYP1B1结合位点的相互作用。

  DOI：

  10.1039/c3md00317e

文献信息

• Synthesis and Bioactivity of Resveratrol Analogues
  作者：Junli Ao、Yuanmou Chen、Xiaoling Xu、Xu Zhang、Yue Yu、Peng Yu、Erbing Hua

  DOI：10.14233/ajchem.2014.16226

  日期：——

  It has been reported that resveratrol enhanced SIRT1 expression and significantly mimicked calorie restriction by stimulating Sir2 which is the most homologic homologue of SIRT1 of mammalian. A series of novel resveratrol derivatives were designed and synthesized as novel SIRT1 activator candidates. These synthesized compounds were characterized by spectral (1H NMR) analysis and examined for their Sir2 activation against yeast parental strain-BY4743 at a concentration of 100 μM/L by Bioscreen C MBR machine. Several compounds showed a promising Sir2 activation activity compared with resveratrol. Meanwhile, the structure-activity relationships with Sirt2 activation activities were also discussed.

  据报道，白藜芦醇能够增强SIRT1的表达，并通过刺激与哺乳动物SIRT1具有高度同源性的Sir2，显著模拟热量限制的效果。设计并合成了系列新型白藜芦醇衍生物，作为新型SIRT1激动剂的候选物质。通过核磁共振(1H NMR)光谱分析对合成的化合物进行了表征，并利用Bioscreen C MBR机器在100 μM/L浓度下检测了这些化合物对酵母亲本菌株BY4743的Sir2激活作用。与白藜芦醇相比，多个化合物表现出良好的Sir2激活活性。同时，还讨论了这些化合物的结构-活性关系与Sir2激活活性的相关性。
• The total synthesis of salvianolic acid F
  作者：Vincent Dalla、Philippe Cotelle

  DOI：10.1016/s0040-4020(99)00321-x

  日期：1999.5

  An expeditious synthesis of salvianolic acid F 2 is described in 10% overall yield. Tetramethyl salvianolic acid F 3 was obtained in six steps in 39% overall yield and was converted into the target molecule using boron tribromide in 26% yield.

  以10％的总收率描述了快速合成丹酚酸F 2的方法。通过六步获得四甲基丹酚酸F 3，总产率为39％，并使用三溴化硼将其转化为目标分子，产率为26％。
• 3,4,2′-Trimethoxy-trans-stilbene – a potent CYP1B1 inhibitor
  作者：Renata Mikstacka、Marcin Wierzchowski、Zbigniew Dutkiewicz、Agnieszka Gielara-Korzańska、Artur Korzański、Anna Teubert、Stanisław Sobiak、Wanda Baer-Dubowska

  DOI：10.1039/c3md00317e

  日期：——

  A novel series of methoxy-trans-stilbenes with 3,4-dimethoxy motifs was designed and synthesized. The inhibitory potency of 3,4-dimethoxystilbene derivatives against cytochrome P450 isozymes CYP1A1, CYP1B1 and CYP1A2 was evaluated. 3,4,2′-Trimethoxy-trans-stilbene (3,4,2′-TMS) exhibited extremely potent inhibitory action against CYP1B1 activity with an IC50 of 0.004 μM. 3,4,2′-TMS exhibited 90-fold selectivity for CYP1B1 over CYP1A1 and 830-fold selectivity for CYP1B1 over CYP1A2. However, 3,4,2′,4′-tetramethoxy-trans-stilbene appeared to be the most selective inhibitor of both CYP1B1 and CYP1A1 showing very low affinity toward CYP1A2. Complementary experimental studies and computational methods were used to explain what structural determinants decide the specific affinity of stilbene derivatives to CYP1A2 and CYP1B1 binding sites.

  一种新型的含有3,4-二甲氧基基团的反式-苯乙烯系列化合物被设计和合成。评估了3,4-二甲氧基苯乙烯衍生物对细胞色素P450同工酶CYP1A1、CYP1B1和CYP1A2的抑制活性。3,4,2′-三甲氧基反式-苯乙烯（3,4,2′-TMS）对CYP1B1活性表现出极强的抑制作用，IC50为0.004 μM。3,4,2′-TMS在CYP1B1与CYP1A1之间表现出90倍的选择性，在CYP1B1与CYP1A2之间表现出830倍的选择性。然而，3,4,2′,4′-四甲氧基反式-苯乙烯似乎是对CYP1B1和CYP1A1最具选择性的抑制剂，对CYP1A2表现出非常低的亲和力。为了说明苯乙烯衍生物特定的亲和力决定因素，补充实验研究和计算方法被用来解释结构特征如何影响与CYP1A2和CYP1B1结合位点的相互作用。