3-(4-isopentenyloxyphenyl)-2-trans-propenoic acid

• 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: 3-(4-isopentenyloxyphenyl)-2-trans-propenoic acid
• 英文别名: 4'-isopentenyloxycinnamic acid；(E)-3-(4-((3-methylbut-2-en-1-yl)oxy)phenyl)acrylic acid；IPaeA；(2E)-3-{4-[(3-methylbut-2-enyl)oxy]phenyl}prop-2-enoic acid；(E)-3-[4-(3-methylbut-2-enyloxy)phenyl]-prop-2-enoic acid；3-(4'-isopent-2-enyloxyphenyl)-2-trans-propenoic acid；isopentenyloxy-p-coumaric acid；(E)-3-[4-(3-methylbut-2-enoxy)phenyl]prop-2-enoic acid
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: VWGXUJRWFSNPCG-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-isopentenyloxyphenyl)-2-trans-propenoic acid 、 盐酸肼屈嗪 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以77%的产率得到(2E,N',E)-3-[4-(3-ethylbut-2-enyloxy)phenyl]-N'-(phthalazin-1-(2H)-ylidiene)acrylohydrazide
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of New Cinnamic Derivatives as Antituberculosis Agents

  摘要：

  Tuberculosis, HIV coinfection with TB, emergence of multidrug-resistant TB, and extensively drug-resistant TB are the major causes of death from infectious diseases worldwide. Because no new drug has been introduced in the last several decades, new classes of molecules as anti-TB drugs are urgently needed. Herein, we report the synthesis and structure-activity relationships of a series of thioester, amide, hydrazide, and triazolophthalazine derivatives of 4-alkoxy cinnamic acid. Many compounds exhibited submicromolar minimum inhibitory concentrations against Mycobacterium tuberculosis strain (H(37)Rv). Interestingly, compound 13e, a 4-isopentenyloxycinnamyl triazolophthalazine derivative, was found to be 100-1800 times more active than isoniazid (INH) when tested for its ability to inhibit the growth of INH-resistant M. tuberculosis strains. The results also revealed that 13e does not interfere with mycolic acid biosynthesis, thereby pointing to a different mode of action and representing an attractive lead compound for the development of new anti-TB agents.

  DOI：

  10.1021/jm101510d
• 作为产物：
  描述：

  4-香豆酸 在 硫酸 、 potassium carbonate 、 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 15.25h， 生成 3-(4-isopentenyloxyphenyl)-2-trans-propenoic acid
  参考文献：
  名称：

  Prenylated Trans-Cinnamic Esters and Ethers against Clinical Fusarium spp.: Repositioning of Natural Compounds in Antimicrobial Discovery

  摘要：

  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。

  DOI：

  10.3390/molecules26030658

文献信息

• Natural and semisynthetic oxyprenylated aromatic compounds as stimulators or inhibitors of melanogenesis
  作者：Salvatore Genovese、Francesco Epifano、Philippe de Medina、Nicolas Caron、Arnaud Rives、Marc Poirot、Sandrine Silvente-Poirot、Serena Fiorito

  DOI：10.1016/j.bioorg.2019.03.026

  日期：2019.6

  benzoic acids, cinnamaldehydes, benzaldehyde, and anthraquinone derivatives. A total number of 43 compounds have been tested assaying their capacity to inhibit or stimulate melanin biosynthesis in cultured murine Melan A cells. The wider number of chemicals herein under investigation allowed to depict a detailed structure-activity relationship, as the following: (a) benzoic acid derivatives are slightly

  最近已经表明，天然存在的氧戊烯化香豆素是有效的黑色素生成调节剂。在此简短的交流中，我们希望概括一下更广泛的天然和半合成芳族化合物（包括香豆素，肉桂酸和苯甲酸，肉桂醛，苯甲醛和蒽醌衍生物）作为皮肤美黑或增白剂的潜力。总共测试了43种化合物，分析了它们在培养的鼠Melan A细胞中抑制或刺激黑色素生物合成的能力。本文所研究的大量化学物质可描述出详细的结构与活性的关系，如下所示：（a）苯甲酸衍生物是轻微的色素形成剂，对于具有较长O的化合物，其作用更为明显。-侧链；（b）与取代类型无关，肉桂酸能够增加黑色素的生物合成，而苯甲醛能够减少黑色素的生物合成；（c）在7位具有3,3-二甲基烯丙基或更短骨架作为取代基的香豆素为鞣制剂，而具有法呢烷氧基的香豆素为增白剂；（d）在6和7位上的双氧基戊烯基化和3,3-二甲基烯丙基或香叶基骨架具有轻微的脱色能力，而法呢基骨架则倾向于略微提高鞣制效果；（e）在香豆素核
• [EN] SKIN PIGMENTATION MODIFIERS TO DARKEN OR LIGHTEN THE SKIN<br/>[FR] AGENTS DE MODIFICATION DE LA PIGMENTATION DE LA PEAU EN VUE DE L'ASSOMBRIR OU DE L'ÉCLAIRCIR
  申请人：AFFICHEM

  公开号：WO2016193220A1

  公开（公告）日：2016-12-08

  The present invention relates to a method for changing the pigmentation of a skin, a mucous membrane or hair with a compound of general formula (I), a cosmetic use of said compound of general formula (I), to cosmetic compositions comprising said compound of general formula (I), and to new depigmenting agents.

  本发明涉及一种改变皮肤、粘膜或头发色素的方法，使用一般式(I)的化合物，以及所述一般式(I)的化合物的化妆用途，包括所述一般式(I)的化合物的化妆组合物，以及新的脱色剂。
• 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。
• 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。
• Design, Synthesis, and Biological Evaluation of New Cinnamic Derivatives as Antituberculosis Agents
  作者：Prithwiraj De、Georges Koumba Yoya、Patricia Constant、Florence Bedos-Belval、Hubert Duran、Nathalie Saffon、Mamadou Daffé、Michel Baltas

  DOI：10.1021/jm101510d

  日期：2011.3.10

  Tuberculosis, HIV coinfection with TB, emergence of multidrug-resistant TB, and extensively drug-resistant TB are the major causes of death from infectious diseases worldwide. Because no new drug has been introduced in the last several decades, new classes of molecules as anti-TB drugs are urgently needed. Herein, we report the synthesis and structure-activity relationships of a series of thioester, amide, hydrazide, and triazolophthalazine derivatives of 4-alkoxy cinnamic acid. Many compounds exhibited submicromolar minimum inhibitory concentrations against Mycobacterium tuberculosis strain (H(37)Rv). Interestingly, compound 13e, a 4-isopentenyloxycinnamyl triazolophthalazine derivative, was found to be 100-1800 times more active than isoniazid (INH) when tested for its ability to inhibit the growth of INH-resistant M. tuberculosis strains. The results also revealed that 13e does not interfere with mycolic acid biosynthesis, thereby pointing to a different mode of action and representing an attractive lead compound for the development of new anti-TB agents.