4'-Geranyloxyferulic acid | 870073-93-1

• 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: 4'-Geranyloxyferulic acid
• 英文别名: 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans-propenoic acid；(E)-3-[4-[(2E)-3,7-dimethylocta-2,6-dienoxy]-3-methoxyphenyl]prop-2-enoic acid
• CAS: 870073-93-1
• 化学式: C₂₀H₂₆O₄
• 分子量: 330.424
• InChiKey: WAHYZVVZFNUXSC-TWGDSDBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  4'-Geranyloxyferulic acid 在 sodium hydroxide 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 7.0h， 生成 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans-propenoyl-L-alanine
  参考文献：
  名称：

  Synthesis of a novel prodrug of 3-(4′-geranyloxy-3′-methoxyphenyl)-2-trans-propenoic acid for colon delivery

  摘要：

  A novel high-yielding and environment-friendly synthesis of the anticancer compound 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans-propenoic acid is described. This compound was conjugated to H2N-Ala-Pro dipeptide to give a prodrug to be activated by intestinal ACE and to be used in the treatment of different forms of colon cancer. Data on the chemical and enzymatic stability of this novel prodrug are reported. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.088
• 作为产物：
  描述：

  阿魏酸 在 硫酸 作用下， 以 丙酮 为溶剂， 反应 14.0h， 生成 4'-Geranyloxyferulic acid
  参考文献：
  名称：

  7-烷氧基香豆素与芳烃受体的相互作用

  摘要：

  芳基烃受体（AhR）是被大量天然和合成配体激活的转录因子。它在许多生理和病理反应中起着关键作用，例如细胞增殖和分化，异种生物代谢酶的诱导，对环境毒素的反应等。在这项研究中，我们使用报告荧光素酶测定法研究了某些天然化合物（氧炔丙基阿魏酸和伞形酮衍生物）及其半合成类似物（例如，不同取代的7-烷氧基香豆素）激活AhR的能力。其中，我们发现7-异戊烯氧基香豆素是最好的AhR活化剂。七氢硼酸，7-but-2'-烯氧基香豆素，7-（2'，2'-二甲基-n-丙氧基）香豆素，7-苄氧基香豆素和7-（3'-羟甲基-3'-甲基烯丙氧基）香豆素也有活性，尽管程度较小。还使用参考配体6-甲酰基吲哚并[3,2- b ]咔唑分析了所有化合物抑制AhR活化的能力。在本研究中记录的数据指出，连接到香豆素环核上的3,3-二甲基烯丙氧基侧链作为AhR激活的关键部分的重要性。

  DOI：

  10.1021/acs.jnatprod.7b00173

文献信息

• Effects of 3-(4′-geranyloxy-3′-methoxyphenyl)-2-trans propenoic acid and its ester derivatives on biofilm formation by two oral pathogens, Porphyromonas gingivalis and Streptococcus mutans
  作者：Charles Bodet、Francesco Epifano、Salvatore Genovese、Massimo Curini、Daniel Grenier

  DOI：10.1016/j.ejmech.2007.11.001

  日期：2008.8

  The aim of this study was to investigate the effect of 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid, active principle isolated from Acronychia baueri Schott, and its ester derivatives on biofilm formation by two important oral pathogens, Porphyromonas gingivalis and Streptococcus mutans. The parent acid and conjugates with vanillic acid, 2-hydroxynaphthoquinone and guaiacol caused a significant

  这项研究的目的是研究3-（4'-香叶基氧基-3'-甲氧基苯基）-2-反式丙酸（从Acronychia baueri Schott分离的活性成分）及其酯衍生物对两种重要口服液对生物膜形成的影响。病原体，牙龈卟啉单胞菌和变形链球菌。母体酸和与香草酸，2-羟基萘醌和愈创木酚的共轭物对牙龈卟啉单胞菌生物膜形成产生了明显且可重现的抑制作用。该作用可能与化合物抑制细菌生长的能力有关。这些化合物还有效地引起了变形链球菌生物膜形成的减少，这种现象与生长抑制无关。这些数据表明3-（4'-香叶基氧基-3'
• 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。
• Synthesis and anti-inflammatory activity of 3-(4′-geranyloxy-3′-methoxyphenyl)-2-trans propenoic acid and its ester derivatives
  作者：Francesco Epifano、Salvatore Genovese、Silvio Sosa、Aurelia Tubaro、Massimo Curini

  DOI：10.1016/j.bmcl.2007.07.058

  日期：2007.10

  Different esters of 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid (1), an anti-inflammatory principle of Acronychia baueri Schott (Rutaceae), were synthesized. Their topical anti-inflammatory activity was evaluated using the Croton oil ear test in mice as a model of acute inflammation. The activity of the paracetamol, guaiacol and hydroquinone esters of (1) was higher than that of the parent

  合成了3-（4'-香叶基氧基-3'-甲氧基苯基）-2-反式丙酸的不同酯（Acronychia baueri Schott（芸苔科）的抗炎成分）。使用巴豆油耳试验在小鼠中作为急性炎症的模型，评估了它们的局部抗炎活性。（1）的对乙酰氨基酚，愈创木酚和对苯二酚酯的活性高于母体化合物的活性，类似于吲哚美辛用作对照药物。
• 알콕시페닐프로펜온 유도체 또는 이의 약학적으로 허용가능한 염 및 이를 유효성분으로 함유하는 퇴행성 뇌질환의 예방 또는 치료용 약학적 조성물
  申请人：Ewha University - Industry Collaboration Foundation 이화여자대학교 산학협력단(220040083301) BRN ▼110-82-10456

  公开号：KR101599525B1

  公开（公告）日：2016-03-03

  본 발명은 알콕시페닐프로펜온 또는 이의 약학적으로 허용가능한 염 및 이를 유효성분으로 함유하는 퇴행성 뇌질환의 예방 또는 치료용 약학적 조성물에 관한 것이다. 본 발명에 의한 알콕시페닐프로펜온 유도체는 산화를 유도한 뇌신경 세포에 대하여 보호효과가 종래 비타민 E와 같이 항산화 역할을 하는 트롤록스보다 뇌신경 세포의 보호 효과가 매우 우수하므로 퇴행성 뇌질환의 예방 또는 치료용 약학적 조성물 또는 뇌신경 세포 보호용 약학적 조성물로 유용하게 사용될 수 있다.

  本发明涉及一种用于预防或治疗退行性脑疾病的药学组合物，其包含阿尔科西非利酚丙酮或其药学上可接受的盐及其作为有效成分。根据本发明的阿尔科西非利酚丙酮衍生物对氧化诱导的脑神经细胞具有保护作用，其保护效果对脑神经细胞比传统的抗氧化剂如维生素E等具有更卓越的效果，因此可用作预防或治疗退行性脑疾病的药学组合物或脑神经细胞保护的药学组合物。
• DEPIGMENTING AGENTS TO LIGHTEN THE SKIN
  申请人：Affichem

  公开号：EP3097904A1

  公开（公告）日：2016-11-30

  The present invention relates to a method for lightening a skin or a mucous membrane with a depigmenting agent, a cosmetic use of said depigmenting agent, to cosmetic compositions comprising said agent, and to new depigmenting agents.

  本发明涉及一种使用脱色剂淡化皮肤或粘膜的方法、所述脱色剂的化妆品用途、包含所述脱色剂的化妆品组合物以及新型脱色剂。