(E)-3-(4-(allyloxy)-3-methoxyphenyl)acrylic acid | 115375-24-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(4-(allyloxy)-3-methoxyphenyl)acrylic acid
• 英文别名: (2E)-3-[3-methoxy-4-(prop-2-en-1-yloxy)phenyl]prop-2-enoic acid；(E)-3-(3-methoxy-4-prop-2-enoxyphenyl)prop-2-enoic acid
• CAS: 115375-24-1
• 化学式: C₁₃H₁₄O₄
• mdl: MFCD02256147
• 分子量: 234.252
• InChiKey: XCJIINFOALCIPH-FNORWQNLSA-N

物化性质

• 沸点：
  399.2±32.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.153
• 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)-3-(4-(allyloxy)-3-methoxyphenyl)acrylic acid 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 草酰氯 、 甲酸铵 、 sodium hydride 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 乙腈 、 mineral oil 为溶剂， 反应 48.0h， 生成 N-Methylferulanilid
  参考文献：
  名称：

  阿魏酸衍生物的光异构化的深入研究

  摘要：

  阿魏酸衍生的酯，酰胺和酮的光异构化进行了全面的研究。仅在脂族叔酰胺的情况下，才实现了几乎完全的E→Z转化。

  DOI：

  10.1002/ejoc.202100064
• 作为产物：
  描述：

  阿魏酸 在 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 42.0h， 生成 (E)-3-(4-(allyloxy)-3-methoxyphenyl)acrylic acid
  参考文献：
  名称：

  多组分，基于片段的多酚类肽模拟物的合成及其对β-淀粉样蛋白低聚的抑制活性

  摘要：

  利用含酚的简单底物的Ugi多组分反应，已经开发了一种新的基于短片段的人工（但基于“天然”）复杂多酚的方法。已经测试了所得化合物库抑制β淀粉样蛋白聚集的能力，这是开发新的化学实体以用作预防或治疗阿尔茨海默氏病的可能策略。该库的某些成员在硫黄素分析中证明了在抑制两个β淀粉样肽：Aβ1-42和截短的AβpE3-42聚集方面具有非常有前途的活性。

  DOI：

  10.1039/c7ob02182h

文献信息

• Prenylated Trans-Cinnamic Esters and Ethers against Clinical Fusarium spp.: Repositioning of Natural Compounds in Antimicrobial Discovery
  作者：Safa Oufensou、Stefano Casalini、Virgilio Balmas、Paola Carta、Wiem Chtioui、Maria A. Dettori、Davide Fabbri、Quirico Migheli、Giovanna Delogu

  DOI：10.3390/molecules26030658

  日期：——

  Onychomycosis is a common nail infection mainly caused by species belonging to the F. oxysporum, F. solani, and F. fujikuroi species complexes. The aim of this study was to evaluate the in vitro susceptibility of six representative strains of clinically relevant Fusarium spp. toward a set of natural-occurring hydroxycinnamic acids and their derivatives with the purpose to develop naturally occurring products in order to cope with emerging resistance phenomena. By introducing a prenylated chain at one of the hydroxy groups of trans-cinnamic acids 1–3, ten prenylated derivatives (coded 4–13) were preliminarily investigated in solid Fusarium minimal medium (FMM). Minimal inhibitory concentration (MIC) and lethal dose 50 (LD50) values were then determined in liquid FMM for the most active selected antifungal p-coumaric acid 3,3′-dimethyl allyl ester 13, in comparison with the conventional fungicides terbinafine (TRB) and amphotericin B (AmB), through the quantification of the fungal growth. Significant growth inhibition was observed for prenylated derivatives 4–13, evidencing ester 13 as the most active. This compound presented MIC and LD50 values (62–250 µM and 7.8–125 µM, respectively) comparable to those determined for TRB and AmB in the majority of the tested pathogenic strains. The position and size of the prenylated chain and the presence of a free phenol OH group appear crucial for the antifungal activity. This work represents the first report on the activity of prenylated cinnamic esters and ethers against clinical Fusarium spp. and opens new avenues in the development of alternative antifungal compounds based on a drug repositioning strategy.

  Onychomycosis是一种常见的指甲感染，主要由属于F. oxysporum、F. solani和F. fujikuroi物种复合体的物种引起。本研究旨在评估临床相关的六株代表性Fusarium spp.菌株对一组天然存在的羟基肉桂酸及其衍生物的体外敏感性，以开发天然产物，以应对新兴的耐药现象。通过在对固体Fusarium最小培养基（FMM）中引入一种烯丙基链到反式肉桂酸1-3的羟基中的十种烯丙基衍生物（编码为4-13），对其进行了初步研究。然后，在液体FMM中确定了对最活性的选定抗真菌p-香豆酸3,3'-二甲基烯丙酯13的最小抑制浓度（MIC）和半数致死量50（LD50）值，与常规杀菌剂特比萘啶（TRB）和两性霉素B（AmB）进行比较，通过对真菌生长的定量化。对于烯丙基衍生物4-13观察到显著的生长抑制，表明酯13是最活性的。该化合物的MIC和LD50值（分别为62-250 µM和7.8-125 µM）与大多数测试的致病菌株中确定的TRB和AmB的值相当。烯丙基链的位置和大小以及自由酚羟基的存在似乎对抗真菌活性至关重要。这项工作是关于烯丙基肉桂酸酯和醚对临床Fusarium spp.的活性的首次报告，并为基于药物再定位策略开发替代抗真菌化合物开辟了新途径。
• ROSMARINIC ACID DERIVATIVE OR SALT THEREOF
  申请人：KAO CORPORATION

  公开号：US20210300859A1

  公开（公告）日：2021-09-30

  The present invention provides a compound that inhibits the activity of TRPV4 and is useful for prevention or amelioration of an overactive bladder, an irritable bowel syndrome, etc. The compound is a rosmarinic acid derivative represented by the following formula (I) or a salt thereof:

  本发明提供了一种抑制TRPV4活性的化合物，可用于预防或改善过度活跃的膀胱、肠易激综合征等。该化合物是以下式（I）所代表的迷迭香酸衍生物或其盐：
• First diastereoselective synthesis of methyl caffeoyl- and feruloyl-muco-quinates
  作者：Rakesh Jaiswal、Michael H. Dickman、Nikolai Kuhnert

  DOI：10.1039/c2ob25124h

  日期：——

  We report on a diastereoselective synthesis of six derivatives of caffeoyl- and feruloyl-muco-quinic acids. All the muco-quinic acid derivatives were obtained in excellent yield in five steps starting from quinic acid, caffeic acid and ferulic acid. Allyl ether protection of trans-hydroxy cinnamic acids was here introduced to chlorogenic acids synthesis. We show that muco-quinic acid derivatives, which are formally diastereoisomers of chlorogenic acids, can be readily distinguished by their tandem mass spectra

  我们报告了一种非对映选择性合成咖啡酰基和阿魏酰基粘喹酸六种衍生物的方法。以奎宁酸、咖啡酸和阿魏酸为起点，通过五个步骤获得了所有的黏稠奎宁酸衍生物，收率极高。这里将反式羟基肉桂酸的烯丙基醚保护引入到绿原酸合成中。我们的研究表明，作为绿原酸非对映异构体的粘液喹酸衍生物可以通过串联质谱很容易地区分出来。
• Concise total synthesis of acylated phenolic glycosides vitexnegheteroin A and ovatoside D
  作者：Shiqiang Yan、Sumei Ren、Ning Ding、Yingxia Li

  DOI：10.1016/j.carres.2018.02.015

  日期：2018.5

  glucose, two natural acylated phenolic glycosides vitexnegheteroin A and ovatoside D were synthesized for the first time in 4 steps with overall yields of 54% and 65%, respectively. The key steps involve the directly regioselective O-6 acylation of vanillin β-D-glucopyranoside with acyl chlorides, and simultaneous removal of the allyl protecting groups on the phenolic acid moiety and reduction of the

  从容易获得的香兰素和α-D-乙酰溴葡萄糖开始，分四个步骤首次合成了两个天然的酰化酚类糖皮质激素A和卵磷脂D，总收率分别为54％和65％。关键步骤包括使用酰氯直接将香草醛β-D-吡喃葡萄糖苷进行区域选择性O-6酰化，并同时通过使用Pd（PPh）去除酚酸部分上的烯丙基保护基并降低糖苷配基部分中的醛。一锅内装有3-NaBH4系统。
• Multicomponent Synthesis of Polyphenols and their in vitro Evaluation as Potential β-Amyloid Aggregation Inhibitors
  作者：Galante、Banfi、Baruzzo、Basso、D’Arrigo、Lunaccio、Moni、Riva、Lambruschini

  DOI：10.3390/molecules24142636

  日期：——

  While plant polyphenols possess a variety of biological properties, exploration of chemical diversity around them is still problematic. Here, an example of application of the Ugi multicomponent reaction to the combinatorial assembly of artificial, yet “natural-like”, polyphenols is presented. The synthesized compounds represent a second-generation library directed to the inhibition of β-amyloid protein aggregation. Chiral enantiopure compounds, and polyphenol-β-lactam hybrids have been prepared too. The biochemical assays have highlighted the importance of the key pharmacophores in these compounds. A lead for inhibition of aggregation of truncated protein AβpE3-42 was selected.

  植物多酚具有各种生物学特性，但围绕它们的化学多样性的探索仍然存在问题。在这里，介绍了将Ugi多组分反应应用于人工组装人工但“类似天然”的多酚的实例。合成的化合物代表了一个针对β-淀粉样蛋白聚集抑制的第二代文库。立体手性纯化合物和多酚-β-内酰胺混合物也已制备。生化分析强调了这些化合物中关键药效团的重要性。选择了抑制截短蛋白AβpE3-42聚集的引物。