caffeic acid benzyl ester diacetate | 1338341-04-0

• 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 benzyl ester diacetate
• 英文别名: benzyl 3-(3,4-diacetyloxyphenyl)prop-2-enoate
• CAS: 1338341-04-0
• 化学式: C₂₀H₁₈O₆
• 分子量: 354.359
• InChiKey: NMIXBJFXDQBHRQ-UHFFFAOYSA-N

物化性质

• 沸点：
  509.4±50.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  caffeic acid benzyl ester diacetate 在 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以33%的产率得到caffeic acid benzyl ester
  参考文献：
  名称：

  咖啡酸酯是通过改变细胞内的氧化剂和抗氧化剂的水平，对幼虫的有效杀菌化合物。

  摘要：

  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

  DOI：

  10.3390/biom9080312
• 作为产物：
  描述：

  咖啡酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 caffeic acid benzyl ester diacetate
  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