(E)-4-(3,5-dimethoxystyryl)benzoic acid | 271772-18-0

• 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: (E)-4-(3,5-dimethoxystyryl)benzoic acid
• 英文别名: 4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]benzoic acid
• CAS: 271772-18-0
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: QYPKNQLYYWOQPY-ONEGZZNKSA-N

物化性质

• 熔点：
  223 °C
• 沸点：
  481.3±33.0 °C(predicted)
• 密度：
  1.219±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-4-(3,5-dimethoxystyryl)benzoic acid 在 甲基磺酰氯 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 醋酸异丙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 (E)-N-(2-(1H-imidazol-1-yl)-2-phenylethyl)-4-(3,5-dimethoxystyryl)benzamide
  参考文献：
  名称：

  Small-Molecule Inhibitors of 25-Hydroxyvitamin D-24-Hydroxylase (CYP24A1): Synthesis and Biological Evaluation

  摘要：

  The synthesis of imidazole styrylbenzamide, tert-butyl styryl-imidazole, and tert-butyl styrylsulfonate derivatives is described. Evaluation of binding affinity and inhibitory activity against CYP24A1 identified the imidazole styrylbenzamides as potent inhibitors of CYP24A1, having selectivity with respect to CYP27B1 comparable with or greater than that of the standard ketoconazole. Further evaluation of the 3,5-dimethoxy and 3,4,5-trimethoxy derivatives in chronic lymphocytic leukemia cells revealed that co-treatment of 1 alpha,25-dihydroxyvitamin D-3 plus inhibitor coordinately upregulated GADD45 alpha and CDKN1A. Docking experiments on the inhibitors in the CYP24A1 enzyme active site suggest the compounds reach the active site through the vitamin D access tunnel and are exposed to multiple hydrophobic residues. The imidazole styrylbenzamides are optimally positioned to allow interaction of the imidazole with the heme, and, in the case of the methoxy derivatives, a hydrogen bond between the 3-methoxy group and Gln82 stabilizes the molecule in a favorable active conformation.

  DOI：

  10.1021/jm5009314
• 作为产物：
  描述：

  (E)-methyl 4-(3,5-dimethoxystyryl)benzoate 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以44%的产率得到(E)-4-(3,5-dimethoxystyryl)benzoic acid
  参考文献：
  名称：

  Design, synthesis, biological evaluation and docking studies of pterostilbene analogs inside PPARα

  摘要：

  Pterostilbene, a naturally occurring analog of resveratrol, has previously shown PPAR alpha activation in H4IIEC3 cells and was found to decrease cholesterol levels in animals. In this study, analogs of pterostilbene were synthesized and their ability to activate PPARa was investigated. Among analogs that was synthesized (E)-4-(3,5-dimethoxystyryl) phenyl dihydrogen phosphate showed activity higher than pterostilbene and control drug ciprofibrate. Docking of the stilbenes inside PPARa showed the presence of important hydrogen bond interactions for PPAR alpha activation. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.01.051

文献信息

• PREVENTION AND TREATMENT OF COLON CANCER
  申请人：Rimando Agnes M.

  公开号：US20120178704A1

  公开（公告）日：2012-07-12

  Stilbene compounds for the prevention and treatment of colon cancer or colon inflammation and methods of using same are provided.

  提供了用于预防和治疗结肠癌或结肠炎的双苯乙烯化合物及其使用方法。
• Diethylzinc-promoted carboxylation of aryl/alkenyl boronic acids with CO₂
  作者：Tingyu Tang、Shibiao Tang、Bin Li、Baiquan Wang

  DOI：10.1039/d3ob01552a

  日期：——

  The carboxylation of aryl and alkenyl boronic acids with CO2 is rarely studied and only achieved using copper salts as the catalyst in the presence of a strong base. Herein, we report a diethylzinc-promoted carboxylation of aryl or alkenyl boronic acids with carbon dioxide. The reaction does not require a transition-metal catalyst, and has simple and mild conditions and a broad substrate scope.

  芳基硼酸和烯基硼酸与CO 2的羧化作用很少被研究，并且仅在强碱存在下使用铜盐作为催化剂来实现。在此，我们报道了二乙基锌促进的芳基或烯基硼酸与二氧化碳的羧化。该反应不需要过渡金属催化剂，条件简单温和，底物范围广泛。
• A Structure‐Activity Relationship Study of Amino Acid Derivatives of Pterostilbene Analogues Toward Human Breast Cancer
  作者：Fabiana Cordella、Nicola Dragone、Rosarita D'Orsi、Concetta Saponaro、Daniele Vergara、Marco Lessi、Gaetano Angelici

  DOI：10.1002/cmdc.202300727

  日期：——

  Different analogues of functionalizable Pterostilbene were efficiently synthesized and derivatized with a selected library of antioxidant amino acids. The library was analyzed towards cancer cells. The data demonstrated the enhanced anti-proliferative activity of Tryptophan-conjugated compounds. In breast cancer cells, the treatment with Tryptophan-conjugated analogues induced the activation of cellular

  有效合成了可官能化紫檀芪的不同类似物，并用选定的抗氧化氨基酸库衍生化。对文库进行了癌细胞分析。数据证明色氨酸缀合化合物的抗增殖活性增强。在乳腺癌细胞中，色氨酸缀合类似物的治疗诱导细胞应激途径的激活，包括自噬信号传导。
• WO2008/70872
  申请人：——

  公开号：——

  公开（公告）日：——
• US8426369B2
  申请人：——

  公开号：US8426369B2

  公开（公告）日：2013-04-23