(E)-2-hydroxy-6-(tridec-1-enyl)benzoic acid | 1304514-06-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-2-hydroxy-6-(tridec-1-enyl)benzoic acid
• 英文别名: (E)-2-hydroxy-6-(tridec-1-en-1-yl)benzoic acid；(E)-6-(1-tridecenyl)salicylic acid；2-hydroxy-6-[(E)-tridec-1-enyl]benzoic acid
• CAS: 1304514-06-4
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: UJXVOXJVVBSHRC-WYMLVPIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,6-二羟基苯甲酸 在 吡啶 、 4-二甲氨基吡啶 、 氯化亚砜 、 水 、 potassium carbonate 、 potassium hydroxide 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.5h， 生成 (E)-2-hydroxy-6-(tridec-1-enyl)benzoic acid
  参考文献：
  名称：

  SUMO化抑制剂银杏酸衍生物的合成与评价

  摘要：

  SUMOylation 已成为一种重要的翻译后修饰，已被证明可调节与各种信号通路相关的蛋白质活性，因此，它已成为重要的治疗靶点。虽然几种天然产物已被证明可以抑制参与 SUMOylation 过程的酶，但在开发更具选择性和效力的 SUMOylation 抑制剂方面进展甚微。银杏酸是最早发现的可抑制 SUMO E1 酶的天然产物之一。尽管它用于机械研究 SUMO 化过程，银杏酸也调节其他途径。在这封信中，介绍了银杏酸作为 SUMO 化抑制剂的初步构效关系。

  DOI：

  10.1021/acsmedchemlett.0c00353

文献信息

• Synthesis of Ginkgolic Acid Analogues and Evaluation of Their Molluscicidal Activity
  作者：Peng Zhang、Jiahu Pan、Wanxing Duan、Xuedong Li、Yao Zhang、Yibiao Zhou、Qingwu Jiang、Zuohua Mao、Peizhong Yu

  DOI：10.3390/molecules16054059

  日期：——

  Based on the molluscicidal activity of ginkgolic acids (GAs) isolated from Ginkgo biloba L, a series of Z/E isomers of GA analogues were prepared and evaluated for their molluscicidal activities against the host snail Oncomelania hupensis. The results and analysis of the structure-activity relationship revealed that the E-isomers showed better molluscicidal activities than their Z-isomers. Molluscicidal activities decreased with the shortening of the alkenyl chain lengths.

  基于从银杏叶中分离得到的银杏酸（GAs）的杀螺活性，制备了一系列GAs类似物的Z/E异构体，并评估了它们对中间宿主钉螺（Oncomelania hupensis）的杀螺活性。结果及结构-活性关系分析表明，E-异构体显示出比其Z-异构体更好的杀螺活性。随着烯烃链长度的缩短，杀螺活性下降。
• Novel Chemical Synthesis of Ginkgolic Acid (13:0) and Evaluation of Its Tyrosinase Inhibitory Activity
  作者：Yuanqing Fu、Shan Hong、Duo Li、Songbai Liu

  DOI：10.1021/jf4012642

  日期：2013.6.5

  A novel efficient synthesis of ginkgolic acid (13:0) from abundant 2,6-dihydroxybenzoic acid was successfully developed through a state-of-the-art palladium-catalyzed cross-coupling reaction and catalytic hydrogenation with an overall yield of 34% in five steps. The identity of the synthesized ginkgolic acid (13:0) was confirmed by nuclear magnetic resonance, mass spectrometry, infrared, and high-performance liquid chromatography. The reaction sequence of this method can be readily extended to the synthesis of other ginkgolic acids. The synthesized ginkgolic acid (13:0) exhibited promising anti-tyrosinase activity (IC50 = 2.8 mg/mL) that was not correlated to antioxidant activity as probed by 1,1-diphenyl-2-picrylhydrazyl, 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid), ferric reducing ability of plasma, and oxygen radical absorbance capacity assays. The synthetic strategy developed in this work will significantly facilitate biological studies of ginkgolic acids that have great potential applications in food and pharmaceuticals.