4-异戊烯基氧基肉桂酸甲酯 | 81053-49-8

• 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
• 中文名称: 4-异戊烯基氧基肉桂酸甲酯
• 英文名称: methyl (E)-4-(3'-methylbut-2'-enyloxy)cinnamate
• 英文别名: Methyl 4-prenyloxycinnamate；methyl (E)-3-[4-(3-methylbut-2-enoxy)phenyl]prop-2-enoate
• CAS: 81053-49-8
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: DBMLKNYVORYESN-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 储存条件：
  2-8℃

反应信息

• 作为反应物：
  描述：

  4-异戊烯基氧基肉桂酸甲酯 在 水 、 potassium carbonate 、 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 甲醇 、 乙腈 为溶剂， 反应 27.0h， 生成 (E)-3-[4-(3-methylbut-2-enyloxy)styryl]-[ 1,2,4]triazolo[3,4-α]phthalazine
  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 作用下， 以 丙酮 为溶剂， 反应 12.25h， 生成 4-异戊烯基氧基肉桂酸甲酯
  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

• Synthesis of C- and O-prenylated tetrahydroxystilbenes and O-prenylated cinnamates and their action towards cancer cells
  作者：Nooshin Koolaji、Abdallah Abu-Mellal、Van H. Tran、Rujee K. Duke、Colin C. Duke

  DOI：10.1016/j.ejmech.2013.02.017

  日期：2013.5

  first carried out by base catalysed allyl ether formation between 3,3-dimethylallyl bromide and hydroxycinnamic acid methyl ester. The methyl group of the isoprenyl unit was subsequently oxidized using selenium dioxide to form a terminal hydroxyl group. The prenylated tetrahydroxystilbenes and cinnamate synthesized in this study were novel derivatives of piceatannol and methyl 4-(3′-methylbut-2′-enyloxy)cinnamate

  天然存在的C-和O-炔丙基化的四羟基对苯二甲酸酯和O-炔丙基化的肉桂酸酯的合成分别通过脱羰Heck反应和二氧化硒催化的氧化来进行。在decarbonylative赫克合成路线，苯甲酰氯和苯乙烯衍生物的融合物通过一个催化Ñ产生-杂环卡宾系统在原位由乙酸钯和1,3-双（2,6-二异丙基）咪唑啉鎓氯化物，以形成ë -tetrahydroxystilbene衍生物。随后通过使ether的A苯环中的脱保护OH与3,3-二甲基烯丙基溴和碱（氢化钠）反应形成烯丙基醚O-烯丙基化的四羟基sti衍生物。[1,5]从异戊二烯单元的-Rearrangement ø -到ç -位在A环是在升高的温度下在硅酸镁（硅酸镁载体）的存在下进行，形成相应的Ç -prenylated二苯乙烯。O的形成首先，通过在3，3-二甲基烯丙基溴和羟基肉桂酸甲酯之间进行碱催化的烯丙基醚形成反应，使烯丙基-肉桂酸酯化。随后使用二氧化硒氧化
• Synthesis and anticancer activity evaluation of 2(4-alkoxyphenyl)cyclopropyl hydrazides and triazolo phthalazines
  作者：Prithwiraj De、Michel Baltas、Delphine Lamoral-Theys、Céline Bruyère、Robert Kiss、Florence Bedos-Belval、Nathalie Saffon

  DOI：10.1016/j.bmc.2010.02.041

  日期：2010.4

  A series of new 2(4-alkoxyphenyl) cyclopropyl hydrazide-and triazolo-derivatives were synthesized starting from 4-hydroxycinnamic acid (1) in a clean, mild, efficient and straightforward synthetic protocol. These compounds consisting of different alkoxy substitution, phenylcyclopropyl backbone and different heterocyclic groups were evaluated for in vitro anticancer activity against 4 cell lines displaying certain levels of resistance to pro-apoptotic stimuli and 2 cell lines sensitive to pro-apoptotic compounds. Compounds 7f and 8e were most active and displaying moderate in vitro cytostatic effect through different mechanisms. Significantly, chemically modified derivatives could be obtained in order to develop novel types of compounds aiming to combat apoptosis-resistant cancers, for example, those cancers associated with dismal prognoses. (C) 2010 Elsevier Ltd. All rights reserved.
• Sorensen,J.S. et al., Australian Journal of Chemistry, 1968, vol. 21, p. 2037 - 2051
  作者：Sorensen,J.S. et al.

  DOI：——

  日期：——
• Monache, Franco Delle; Monache, Giuliano Delle; Souza, Maria Alves De Moraes e, Gazzetta Chimica Italiana, 1989, vol. 119, # 8, p. 435 - 440
  作者：Monache, Franco Delle、Monache, Giuliano Delle、Souza, Maria Alves De Moraes e、Cavalcanti, Maria Da Salete、Chiappeta, Alda

  DOI：——

  日期：——
• DELLE, MONACHE FRANCO;DELLE, MONACHE GIULIANO;ALVES, DE MORAES E SOUZA MA+, GAZZ. CHIM. ITAL., 119,(1989) N, C. 435-439
  作者：DELLE, MONACHE FRANCO、DELLE, MONACHE GIULIANO、ALVES, DE MORAES E SOUZA MA+

  DOI：——

  日期：——