caffeic acid phenethyl ester diacetate | 1338341-03-9

• 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 phenethyl ester diacetate
• 英文别名: Ac-CAPE；2-Phenylethyl 3-(3,4-diacetyloxyphenyl)prop-2-enoate；2-phenylethyl 3-(3,4-diacetyloxyphenyl)prop-2-enoate
• CAS: 1338341-03-9
• 化学式: C₂₁H₂₀O₆
• 分子量: 368.386
• InChiKey: ZYZMRZIODPGYSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  caffeic acid phenethyl ester diacetate 在 palladium 10% on activated carbon 、 氢气 、 盐酸胍 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 2-phenylethyl 3-(3,4-dihydroxyphenyl)propanoate
  参考文献：
  名称：

  咖啡酸苯乙酯及其相关丙酸、乙酸和苯甲酸类似物的合成和抗自由基/抗氧化活性。

  摘要：

  咖啡酸苯乙酯 (CAPE) 是一种从蜂胶中分离出来的生物活性成分。合成了一系列 CAPE 类似物并分析了它们的抗自由基/抗氧化作用。双键和共轭体系的存在对抗氧化作用的影响用从3-(3,4-二羟基苯基)丙酸获得的类似物进行评价。那些从 2-(3,4-二羟基苯基) 乙酸和 3,4-二羟基苯甲酸获得的物质可以评估羰基和芳族体系之间存在两个碳的影响。

  DOI：

  10.3390/molecules171214637
• 作为产物：
  描述：

  咖啡酸 在 氯化亚砜 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 caffeic acid phenethyl ester diacetate
  参考文献：
  名称：

  咖啡酸苯乙酯及其相关丙酸、乙酸和苯甲酸类似物的合成和抗自由基/抗氧化活性。

  摘要：

  咖啡酸苯乙酯 (CAPE) 是一种从蜂胶中分离出来的生物活性成分。合成了一系列 CAPE 类似物并分析了它们的抗自由基/抗氧化作用。双键和共轭体系的存在对抗氧化作用的影响用从3-(3,4-二羟基苯基)丙酸获得的类似物进行评价。那些从 2-(3,4-二羟基苯基) 乙酸和 3,4-二羟基苯甲酸获得的物质可以评估羰基和芳族体系之间存在两个碳的影响。

  DOI：

  10.3390/molecules171214637

文献信息

• Caffeic Acid Esters Are Effective Bactericidal Compounds Against Paenibacillus larvae by Altering Intracellular Oxidant and Antioxidant Levels
  作者：William Collins、Noah Lowen、David J. Blake

  DOI：10.3390/biom9080312

  日期：——

  activity against PL to determine the minimum inhibitory concentrations (MICs) and minimum bactericidal concentrations (MBCs). Caffeic acid isopropenyl ester (CAIE), caffeic acid benzyl ester (CABE), and caffeic acid phenethyl ester (CAPE) were the most effective in inhibiting PL growth and killing PL cell with MICs and MBCs of 125 µg/mL when used individually, and a MIC and MBC of 31.25 µg/mL for each compound

  American Foulbrood（AFB）是一种致命的细菌性疾病，会影响and和幼虫蜜蜂。AFB是由形成内生孢子的幼虫Paenibacillus幼虫（PL）引起的。蜂胶含有多种有机化合物，是蜜蜂觅食的产物，是一种主要来自树木中植物性植物的树脂物质。蜂胶中常见的几种咖啡酸酯类化合物已显示出对PL的抗菌活性。在这项研究中，合成，纯化，光谱分析六种不同的咖啡酸酯，并测试它们对PL的活性，以确定最小抑菌浓度（MIC）和最小杀菌浓度（MBC）。咖啡酸异丙烯基酯（CAIE），咖啡酸苄基酯（CABE），单独使用的MIC和MBC为125 µg / mL，而咖啡酸苯乙酯（CAPE）则最能有效抑制PL生长并杀死PL细胞，当使用CAIE时，每种化合物的MIC和MBC分别为31.25 µg / mL CABE和CAPE结合使用可防止PL。这些化合物通过杀菌作用抑制细菌的生长，这种作用显示出细胞被杀死，但在18
• CAFFEIC ACID DERIVATIVES AND THEIR USE IN IMPROVING NEURONAL CELL VIABILITY
  申请人：Liu Junyi

  公开号：US20120129931A1

  公开（公告）日：2012-05-24

  This invention relates to caffeic acid derivatives and improving viability of neuronal cells by contacting neuronal cells by caffeic acid derivatives as shown in the specification.

  本发明涉及咖啡酸衍生物，并通过与咖啡酸衍生物接触神经元细胞来提高神经元细胞的存活能力，如规范中所示。
• USE OF PHENETHYL CAFFEATE DERIVATIVES IN THE PREPARATION OF A MEDICAMENT AGAINST TUMOR ANGIOGENESIS
  申请人：Liu, Junyi

  公开号：EP2687211A1

  公开（公告）日：2014-01-22

  Disclosed is the use of the compounds represented by formula (I) in the preparation of a medicament against tumor angiogenesis, wherein R1 and R2 are each independently C1-C8 alkylidene group or C2-C8 alkenylidene group; A1 and A2 are each independently aryl, isoaryl, or aryl or isoaryl optionally substituted by halogen, -CN, -NO2, -OH, -SH, -OR3, -SR3, -R3, -R3-OR4, -C(O)R3, -S(O)R3, -S(O)2R3, -NR4R5, -C(O)OR3, -C(O)NR4R5, -O(O)CR4, -S(O)CR4 or -NR4(O)CR5, wherein R3 is C1-C4 alkyl, R4 and R5 are each independently hydrogen, C1-C4 alkyl, aryl or substituted aryl; and X and Y are each independently oxygen; and the compound of formula (I) does not include phenethyl caffeate.

  公开了式(I)代表的化合物在制备抗肿瘤血管生成药物中的用途，其中 R1 和 R2 各自独立地为 C1-C8 亚烷基或 C2-C8 亚烯基；A1 和 A2 各自独立地为芳基、异芳基或被卤素、-CN、-NO2、-OH、-SH、-OR3、-SR3、-R3、-R3-OR4、-C(O)R3、-S(O)R3、-S(O)2R3、-NR4R5、-C(O)R3-NR4R5、-C(O)OR3、-C(O)NR4R5、-O(O)CR4、-S(O)CR4 或 -NR4(O)CR5 其中 R3 是 C1-C4 烷基，R4 和 R5 各自独立地是氢、C1-C4 烷基、芳基或取代的芳基；X和Y各自独立地为氧；且式（I）化合物不包括咖啡酸苯乙酯。
• 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.
• US9532967B2
  申请人：——

  公开号：US9532967B2

  公开（公告）日：2017-01-03