2-hydroxy-4-(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)benzaldehyde | 1449372-40-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-4-(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)benzaldehyde
• 英文别名: 2-hydroxy-4-(methoxymethoxy)-3-(3-methylbut-2-enyl)benzaldehyde
• CAS: 1449372-40-0
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: RQUPLBOXROMDCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-hydroxy-4-(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)benzaldehyde 在 potassium carbonate 、 乙酰氯 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 86.0h， 生成 4-Hydroxy-2-methoxy-3-(3-methyl-but-2-enyl)-benzaldehyde
  参考文献：
  名称：

  Licochalcone C 和相关 Licoagrochalones 的区域选择性和可扩展全合成

  摘要：

  公开了一种高达 30 g 规模的甘草查尔酮 C 的新型全合成，它依赖于双-O -MOM 保护的间苯二酚的定向邻位金属化作用进行区域选择性C-异戊二烯化，然后进行金属化-甲酰化，选择性O-脱保护– 甲基化和与对羟基苯乙酮的羟醛反应。还进行了相关的甘草查耳酮 B、C 和 D 的合成。

  DOI：

  10.1002/ejoc.202201226
• 作为产物：
  描述：

  1-溴-3-甲基-2-丁烯 在 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 36.0h， 生成 2-hydroxy-4-(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)benzaldehyde
  参考文献：
  名称：

  Synthesis, Antibacterial Effects, and Toxicity of Licochalcone C

  摘要：

  Drug-resistant bacteria constitute a big barrier against current pharmacotherapy. Efforts are urgent to discover antibacterial drugs with novel chemical and biological features. Our work aimed at the synthesis, evaluation of antibacterial effects, and toxicity of licochalcone C (LCC), a naturally occurring chalcone. The synthetic route included six steps, affording a 10% overall yield. LCC showed effects against Gram-positive bacteria (MIC = 6.2–50.0 µg/mL), Mycobacterium species (MIC = 36.2–125 µg/mL), and Helicobacter pylori (MIC = 25 µg/mL). LCC inhibited the biofilm formation of MSSA and MRSA, demonstrating MBIC50 values of 6.25 μg/mL for both strains. The investigations by fluorescence microscopy, using PI and SYTO9 as fluorophores, indicated that LCC was able to disrupt the S. aureus membrane, similarly to nisin. Systemic toxicity assays using Galleria mellonella larvae showed that LCC was not lethal at 100 µg/mL after 80 h treatment. These data suggest new uses for LCC as a compound with potential applications in antibacterial drug discovery and medical device coating.

  DOI：

  10.3390/ph17050634

文献信息

• Concise synthesis of licochalcone C and its regioisomer, licochalcone H
  作者：Zengtao Wang、Yongkai Cao、Suresh Paudel、Goo Yoon、Seung Hoon Cheon

  DOI：10.1007/s12272-013-0222-3

  日期：2013.12

  Licochalone C (7a) is a retrochalcone isolated from Glycyrrhiza inflata, which shows potent antioxidant properties and inhibition of bacterial growth and cellular respiration. Biological studies have suggested that licochalcone C attenuates the lipopolysaccharide and interferon-gamma induced inflammatory response by decreasing the expression and activity of inducible nitric oxide synthase and modulating the antioxidant network activity of superoxide dismutase, catalase, and glutathione peroxidase activity. Licochalcone C also inhibits NADH-cytochrome C reductase in the membrane fraction of Micrococcus luteus. Since pharmacological activity studies of licochalcone C are ongoing and the yield of the compound is poor from natural product, we report a concise four step synthesis of licochalcone C (7a) and its regioisomer, tentatively called licochalcone H (7b), by employing acid-mediated Claisen-Schmidt condensation as a key step with 6 and 20 % overall yield, respectively.

  Licochalone C (7a) 是一种从膨胀甘草中分离出来的逆查尔酮，具有有效的抗氧化特性并能抑制细菌生长和细胞呼吸。生物学研究表明甘草查尔酮 C 通过降低诱导型一氧化氮合酶的表达和活性以及调节超氧化物歧化酶、过氧化氢酶和谷胱甘肽过氧化物酶活性的抗氧化网络活性来减轻脂多糖和干扰素 γ 诱导的炎症反应。 Licochalcone C 还抑制藤黄微球菌膜部分中的 NADH-细胞色素 C 还原酶。由于甘草查尔酮 C 的药理活性研究正在进行中，并且该化合物的天然产物产率很低，因此我们报告了甘草查尔酮 C (7a) 及其区域异构体（暂称为甘草查尔酮 H (7b)）的简明四步合成，通过使用酸-介导的克莱森-施密特缩合作为关键步骤，总产率分别为 6% 和 20%。