caffeic acid 3-methyl-3-butenyl ester | 120534-18-1

• 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: caffeic acid 3-methyl-3-butenyl ester
• 英文别名: 3-methyl-3-butenyl caffeate；isopent-3-enyl caffeate；3-Methylbut-3-en-1-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate；3-methylbut-3-enyl 3-(3,4-dihydroxyphenyl)prop-2-enoate
• CAS: 120534-18-1
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: APFXJJMDUXKKAG-UHFFFAOYSA-N

物化性质

• 沸点：
  421.1±45.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  咖啡酸 在 氯化亚砜 、 盐酸胍 、 三乙胺 、 N,N-二甲基甲酰胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 caffeic acid 3-methyl-3-butenyl ester
  参考文献：
  名称：

  Antiproliferative, antiandrogenic and cytotoxic effects of novel caffeic acid derivatives in LNCaP human androgen-dependent prostate cancer cells

  摘要：

  Caffeic acid and its naturally occurring derivative caffeic acid phenethyl ester (CAPE) have antiproliferative and cytotoxic properties in a variety of cancer cell lines without displaying significant toxicity toward healthy cells, and are considered to be potential anticancer agents. However, little is known about their effects on prostate cancer cells. We synthesized and evaluated the effects of caffeic acid, CAPE (2) and 18 synthetic derivatives on cell viability and androgen-dependent cell proliferation, subcellular localisation and expression of androgen receptor (AR) and secretion of prostate-specific antigen (PSA) in LNCaP human hormone-dependent prostate cancer cells. Several synthetic derivatives of CAPE were strong, concentration-dependent cytotoxic agents in LNCaP cells with IC50 values in the 6.8-26.6 mu M range, potencies that were up to five-fold greater than that of CAPE (33.7 +/- 4.0 mu M). A number of caffeic acid derivatives were inhibitors of androgen-stimulated LNCaP cell proliferation with concomitant inhibition of DHT-stimulated PSA secretion. Compound 24 was the most cytotoxic and antiproliferative caffeic acid derivative (IC50 values of 6.8 +/- 0.3 and 2.4 +/- 0.8 mu M, respectively) inhibiting DHT-stimulated cell proliferation and PSA secretion statistically significantly at concentrations as low as 0.3 mu M. Exposure to DHT increased cytoplasmic and nuclear AR levels and co-treatment with increasing concentrations of compound 24 or CAPE (2), notably, further increased these levels. In conclusion, a number of synthetic derivatives of caffeic acid are potent inhibitors of androgen-dependent prostate cancer cell proliferation and viability, acting, at least in part, via an antiandrogenic mechanism that involves increased nuclear accumulation of (presumably inactive) AR. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.057

文献信息

• Evaluation of allergens in propolis by ultra-performance liquid chromatography/tandem mass spectrometry
  作者：Claudio Gardana、Paolo Simonetti

  DOI：10.1002/rcm.5025

  日期：2011.6.15

  sensitive ultra‐performance liquid chromatography tandem mass spectrometry analysis (UPLC/MS/MS) for the evaluation of the amount of caffeic acid and its esters with allergenic action in raw propolis samples and commercial formulations. The separation was carried out on a 1.7 μm C18 BEH Shield column and the detection performed by means of electrospray ionization in negative ion mode with multiple reaction

  纯化的蜂胶提取物被用作治疗多种疾病的传统药物。其有益活性主要归因于多酚部分。然而，蜂胶可引起过敏性皮炎，并且人类的致敏率主要在年轻受试者中显着增加。这项研究的目的是开发和验证选择性和灵敏的超高效液相色谱串联质谱分析（UPLC / MS / MS），用于评估蜂胶样品和蜂胶样品中咖啡酸及其酯类的变应原作用。商业配方。分离在1.7μmC 18上进行BEH Shield色谱柱，并通过负离子模式下的电喷雾电离和多反应监测进行检测。通过注入到高分辨率系统（FTICR-MS）中并使用精确的质量测量来完成对前体离子和产物离子公式的确认。误差低于1.4 ppm。标准曲线范围为0.5–10μg/ mL，使用二氢咖啡酸作为内标（IS）。3-甲基-2-丁烯基（3M2B），3-甲基-3-丁烯基（3M3B），2-甲基-2-丁烯基（2M2B），苄基（CABE）的检测下限（LLOD） ，苯乙基咖啡酸（CAPE）和咖啡酸（CA）和IS分别为0
• Antihypertensive effect of caffeic acid and its analogs through dual renin–angiotensin–aldosterone system inhibition
  作者：Khushwant S. Bhullar、Grégoire Lassalle-Claux、Mohamed Touaibia、H.P. Vasantha Rupasinghe

  DOI：10.1016/j.ejphar.2014.02.038

  日期：2014.5

  Hypertension is a crucial risk factor for cardiovascular diseases and contributes to one third of global mortality. In addition to conventional antihypertensive drugs such as captopril. naturally occurring phytochemicals and their analogs are used for reducing the risk and occurrence of hypertension. Herein, we demonstrate the possible use of caffeic acid and its derivatives in the treatment of hypertension through multi-target modulation of renin-angiotensin-aldosterone system (RAAS). Caffeic acid along with its nineteen novel derivatives, chlorogenic acid, quercetin and captopril were all investigated for the inhibition of renin and angiotensin converting enzyme (ACE) activities and production of aldosterone. Compound 22 with CH2CH(Ph)(2) moiety exhibited the strongest renin inhibition (IC50=229 mu M) among all compounds tested (P <= 0.05). Caffeic acid was the weakest renin inhibitor (IC50=5704 mu M) among all the compounds assayed. Similar to renin inhibition, compound 22 (IC50=9.1 mu M) also exhibited about 47 times stronger ACE inhibition compared to the parent compound. Analysis of aldosterone revealed that compound 8 with n-Pr moiety was the strongest modulator of aldosterone production among all the derivatives (P <= 0.05). Toxicity analysis using human fibroblasts (WI-38 cells) confirmed the non-toxic manifestations of caffeic acid and its derivatives in comparison to clinically used drug captopril. (C) 2014 Elsevier B.V. All rights reserved.
• Antiproliferative, antiandrogenic and cytotoxic effects of novel caffeic acid derivatives in LNCaP human androgen-dependent prostate cancer cells
  作者：J. Thomas Sanderson、Hélène Clabault、Cody Patton、Grégoire Lassalle-Claux、Jacques Jean-François、Aurélie F. Paré、Martin J.G. Hébert、Marc E. Surette、Mohamed Touaibia

  DOI：10.1016/j.bmc.2013.08.057

  日期：2013.11

  Caffeic acid and its naturally occurring derivative caffeic acid phenethyl ester (CAPE) have antiproliferative and cytotoxic properties in a variety of cancer cell lines without displaying significant toxicity toward healthy cells, and are considered to be potential anticancer agents. However, little is known about their effects on prostate cancer cells. We synthesized and evaluated the effects of caffeic acid, CAPE (2) and 18 synthetic derivatives on cell viability and androgen-dependent cell proliferation, subcellular localisation and expression of androgen receptor (AR) and secretion of prostate-specific antigen (PSA) in LNCaP human hormone-dependent prostate cancer cells. Several synthetic derivatives of CAPE were strong, concentration-dependent cytotoxic agents in LNCaP cells with IC50 values in the 6.8-26.6 mu M range, potencies that were up to five-fold greater than that of CAPE (33.7 +/- 4.0 mu M). A number of caffeic acid derivatives were inhibitors of androgen-stimulated LNCaP cell proliferation with concomitant inhibition of DHT-stimulated PSA secretion. Compound 24 was the most cytotoxic and antiproliferative caffeic acid derivative (IC50 values of 6.8 +/- 0.3 and 2.4 +/- 0.8 mu M, respectively) inhibiting DHT-stimulated cell proliferation and PSA secretion statistically significantly at concentrations as low as 0.3 mu M. Exposure to DHT increased cytoplasmic and nuclear AR levels and co-treatment with increasing concentrations of compound 24 or CAPE (2), notably, further increased these levels. In conclusion, a number of synthetic derivatives of caffeic acid are potent inhibitors of androgen-dependent prostate cancer cell proliferation and viability, acting, at least in part, via an antiandrogenic mechanism that involves increased nuclear accumulation of (presumably inactive) AR. (C) 2013 Elsevier Ltd. All rights reserved.