isopentyl caffeate | 119644-15-4

• 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: isopentyl caffeate
• 英文别名: 3-Methylbutyl 3-(3,4-dihydroxyphenyl)prop-2-enoate；3-methylbutyl 3-(3,4-dihydroxyphenyl)prop-2-enoate
• CAS: 119644-15-4
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: ARDWPGKUNNUACS-UHFFFAOYSA-N

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：
  0.36
• 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：

  异戊醇 、 咖啡酸 以69%的产率得到isopentyl caffeate
  参考文献：
  名称：

  阿魏酸和咖啡酸衍生物的生物活性评估和构效关系分析

  摘要：

  通过高通量筛选（HTS）方法评估了烷基酯和阿魏酸（FA）和咖啡酸（CA）的NO供体的抗癌活性，并描述了结构与活性之间的关系。与具有相同烷基取代基的FA烷基酯相比，CA烷基酯具有更好的抗癌活性。单硝酸盐和苯基呋喃喃硝酸盐比双硝酸盐更有效。FA的苯磺酰呋喃呋喃硝酸盐，尤其是化合物8b - 8d在抗癌方面表现出更强的活性。

  DOI：

  10.1016/j.bmcl.2012.08.038

文献信息

• Synthesis, Antibacterial Evaluation, and QSAR of Caffeic Acid Derivatives
  作者：Marianna O. Araújo、Hilzeth L. Freire Pessoa、Andressa B. Lira、Yunierkis P. Castillo、Damião P. de Sousa

  DOI：10.1155/2019/3408315

  日期：2019.2.12

  The present study evaluates the antibacterial effects of a set of 16 synthesized caffeic acid ester derivatives against strains of Staphylococcus aureus and Escherichia coli, as well as discusses their structure-activity relationship (SAR). The antibacterial assays were performed using microdilution techniques in 96-well microplates to determine minimal inhibitory concentration (MIC). The results revealed

  本研究评估了一组 16 种合成咖啡酸酯衍生物对金黄色葡萄球菌和大肠杆菌菌株的抗菌作用，并讨论了它们的构效关系 (SAR)。在 96 孔微孔板中使用微量稀释技术进行抗菌测定以确定最小抑菌浓度 (MIC)。结果表明，其中五种化合物表现出强至最佳的抗菌效果。在评估的 16 种酯衍生物中，具有烷基侧链的产物，如咖啡酸丙酯 (3)、咖啡酸丁酯 (6) 和咖啡酸戊酯 (7)，表现出最佳抗菌活性，对大肠杆菌的 MIC 值约为 0.20 μM。只有咖啡酸丁酯 (6) 对金黄色葡萄球菌表现出相同的 MIC。对于带有芳基取代基的产物，对大肠杆菌测试菌株的最佳 MIC 结果为（二-（4-氯苄基））咖啡酸（13）和 0.29 µM 咖啡酸二苯甲酯（10）为 0.23 µM，并且对金黄色葡萄球菌菌株的活性均较低。初步定量构效关系 (QSAR) 分析证实了某些结构特征，例如中位线性碳链和芳环对位的吸电子取代基的存在，有助于增强抗菌活性。
• Antinociceptive properties of caffeic acid derivatives in mice
  作者：Fátima de Campos Buzzi、Caroline Liandra Franzoi、Graziele Antonini、Mauricio Fracasso、Valdir Cechinel Filho、Rosendo Augusto Yunes、Rivaldo Niero

  DOI：10.1016/j.ejmech.2009.06.029

  日期：2009.11

  Ten ester derivatives from caffeic acid were synthesized, and their antinociceptive properties are evaluated in mice. The most active compound, dodecyl ester derivative, exhibited potent and dose-related activity against the writhing test, with a calculated ID50 value of 15.1 (11.9–19.1) μmol/kg and MI of 78.8% being several times more active than reference drugs. It was also effective in other experimental

  合成了十种来自咖啡酸的酯衍生物，并在小鼠中评估了它们的镇痛特性。最具活性的化合物十二烷基酯衍生物对扭体试验表现出有效的剂量相关活性，ID 50值为15.1（11.9-19.1）μmol/ kg，MI为78.8％，是参比药物的几倍。 。它在其他实验模型中也有效，例如福尔马林，辣椒素和谷氨酸诱导的疼痛试验，但在热板试验中无效。尽管尚未阐明其作用机理，但这些结果似乎支持其对疼痛性疾病的治疗潜力。
• New Hydroxycinnamic Acid Esters as Novel 5-Lipoxygenase Inhibitors That Affect Leukotriene Biosynthesis
  作者：Luc H. Boudreau、Grégoire Lassalle-Claux、Marc Cormier、Sébastien Blanchard、Marco S. Doucet、Marc E. Surette、Mohamed Touaibia

  DOI：10.1155/2017/6904634

  日期：——

  participate in chronic inflammatory diseases. 5-lipoxygenase is a key enzyme in the biosynthesis of leukotrienes and is thus a validated therapeutic target. As of today, zileuton remains the only clinically approved 5-lipoxygenase inhibitor; however, its use has been limited due to severe side effects in some patients. Hence, the search for a better 5-lipoxygenase inhibitor continues. In this study, we investigated

  白三烯是炎性介质，其积极参与炎性反应并宿主抵抗病原体。但是，白三烯也参与慢性炎症性疾病。5-脂氧合酶是白三烯生物合成中的关键酶，因此是经过验证的治疗靶标。截至今天，齐留通仍是唯一经临床批准的5-脂氧合酶抑制剂。然而，由于某些患者的严重副作用，其使用受到限制。因此，继续寻找更好的5-脂氧合酶抑制剂。在这项研究中，我们研究了咖啡酸苯乙酯（一种天然存在的5-脂氧合酶抑制剂）的结构类似物，以试图增强对5-脂氧合酶的抑制活性并确定结构-活性关系。研究了这些化合物减弱白三烯生物合成的能力。化合物参照图13和19，与参考分子咖啡酸苯乙酯和齐留通相比，苯丙酯和二苯乙酯显示出显着增强的抑制活性。
• [EN] DRUG FOR TREATING ARTERY-RELATED DISEASES, AND USE THEREOF<br/>[FR] MÉDICAMENT POUR LE TRAITEMENT DE MALADIES ARTÉRIELLES ET SON UTILISATION<br/>[ZH] 用于治疗动脉相关疾病的药物及其用途
  申请人：SHANGHAI INST MATERIA MEDICA CAS

  公开号：WO2021063366A1

  公开（公告）日：2021-04-08

  提供用于治疗动脉相关疾病的药物及其用途。具体地，提供了一类式I化合物在治疗动脉相关疾病中的应用。实验表明，式I化合物对动脉瘤、壁间血肿和/或动脉夹层有显著疗效。
• 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.