(Z)-3-(3,5-dimethoxyphenyl)-2-(4-hydroxyphenyl)acrylic acid | 353227-95-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (Z)-3-(3,5-dimethoxyphenyl)-2-(4-hydroxyphenyl)acrylic acid
• 英文别名: alpha-[(3,5-dimethoxyphenyl)methylene]-4-hydroxy-(alphaZ)-benzeneacetic acid；α-[(3,5-dimethoxyphenyl)methylene]-4-hydroxy-(αZ)-benzeneacetic acid；Z-3-(3,5-Dimethoxyphenyl)-2-(4-hydroxyphenyl)-acrylic acid；(Z)-3-(3,5-dimethoxyphenyl)-2-(4-hydroxyphenyl)prop-2-enoic acid
• CAS: 353227-95-9
• 化学式: C₁₇H₁₆O₅
• 分子量: 300.311
• InChiKey: DSGPFIMSCCULRH-SXGWCWSVSA-N

物化性质

• 熔点：
  135-137 °C
• 沸点：
  461.6±40.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-3-(3,5-dimethoxyphenyl)-2-(4-hydroxyphenyl)acrylic acid 在 喹啉 、 铜 作用下， 生成 紫檀芪
  参考文献：
  名称：

  非凡的自由基清除剂：4-巯基苯甲酸酯

  摘要：

  在过去的十年中，与天然白藜芦醇白藜芦醇相比，开发出更多的活性抗氧化剂和癌症化学预防剂引起了极大的兴趣和兴奋。在这项工作中，基于以下启发而构建了八种白藜芦醇导向的4-巯基对苯二甲酸酯：硫酚应是比酚更强的自由基清除剂，并且它们与galvinoxyl（GO 。）和2,2-diphenyl-1-picrylhydrazyl（DPPH）的反应速率。）甲醇和乙酸乙酯中的自由基是通过在25°C下使用停止流UV / Vis光谱法测量的。动力学分析表明，4-巯基对苯二酚是非凡的自由基清除剂，用四苯乙烯基支架中的4-SH基团取代4-OH基团是提高白藜芦醇自由基清除活性的重要策略。令人惊讶的是，在甲醇中，一些4-巯基对苯二酚的活性是白藜芦醇的10 4倍，比已知的抗氧化剂（α-生育酚，抗坏血酸，槲皮素和trolox）的活性高数十倍至数百倍。基于酸化动力学分析讨论了详细的自由基清除机理。添加乙酸显着降低了GO 。和DPPH

  DOI：

  10.1002/chem.201103897
• 作为产物：
  描述：

  对羟基苯乙酸 在 乙酸酐 、 三乙胺 作用下， 反应 30.0h， 生成 (Z)-3-(3,5-dimethoxyphenyl)-2-(4-hydroxyphenyl)acrylic acid
  参考文献：
  名称：

  Synthesis and structure–Activity relationship studies of cinnamic acid-based novel thiazolidinedione antihyperglycemic agents

  摘要：

  A number of 2,4-thiazolidinedione derivatives of -phenyl substituted cinnamic acid were synthesized and studied for their PPAR agonist activity. The E-isomer of cinnamic acid, 11, showed moderate PPAR transactivation. The corresponding Z-isomer, 23, and double bond reduced derivative, 15, were found to be much less potent. Although the E-isomer showed a moderate PPARgamma transactivation, it demonstrated a strong glucose-lowering effect in a genetic rodent model of diabetes. Results of pharmacokinetic, metabolism and permeability studies are consistent with 11 being an active prodrug with an active metabolite, 14, that has similar glucose lowering and PPARgamma agonist properties. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00393-6

文献信息

• Novel heterocyclic analogs of diphenylethylene compounds
  申请人：——

  公开号：US20030181494A1

  公开（公告）日：2003-09-25

  Novel diphenylethylene compounds and derivatives thereof containing thiazolidinedione or oxazolidinedione moieties are provided which are effective in lowering blood glucose level, serum insulin, triglyceride and free fatty acid levels in animal models of Type II diabetes. The compounds are disclosed as useful for a variety of treatments including the treatment of inflammation, inflammatory and immunological diseases, insulin resistance, hyperlipidemia, coronary artery disease, cancer and multiple sclerosis.

  提供含有噻唑二酮或噁唑二酮基团的新型二苯乙烯化合物及其衍生物，对II型糖尿病动物模型中的降低血糖水平、血清胰岛素、甘油三酯和游离脂肪酸水平具有有效作用。这些化合物被披露为用于多种治疗，包括治疗炎症、炎症和免疫性疾病、胰岛素抵抗、高脂血症、冠状动脉疾病、癌症和多发性硬化等。
• Laccase-Catalyzed Dimerization of Hydroxystilbenes
  作者：Chiara Ponzoni、Elisa Beneventi、Maria Rita Cramarossa、Stefano Raimondi、Giulia Trevisi、Ugo Maria Pagnoni、Sergio Riva、Luca Forti

  DOI：10.1002/adsc.200700043

  日期：2007.6.4

  A series of hydroxystilbenes, analogues of the bioactive phytoalexin resveratrol, were synthesized and submitted to the catalytic action of a laccase from Trametes pubescens in a biphasic system made of ethyl acetate and acetate buffer. Oxidation took place at the 4′-hydroxy (4-hydroxy) position of the hydroxystilbenic moieties, followed by radical-radical coupling dimerization reactions. Most of the

  合成了一系列具有生物活性的植物抗alexin白藜芦醇类似物的羟基苯乙烯，并使其在由乙酸乙酯和乙酸盐缓冲液制成的双相体系中经受了来自Tramets pubescens的漆酶的催化作用。氧化发生在羟基苯乙烯基部分的4'-羟基（4-羟基）位置，随后发生自由基-自由基偶联二聚化反应。分离出的大多数产物均具有良好的收率并得到了充分表征。取决于底物，可以鉴定出三种不同的二聚产物，主要产物通常是4-O-α-ß-5（二氢呋喃样）二聚体。
• Novel diphenylethylene compounds
  申请人：——

  公开号：US20020002200A1

  公开（公告）日：2002-01-03

  Novel dephenylethylene compounds that are administered orally to decrease circulating concentrations of glucose are provided. The effect on insulin resistant rats is also shown. The effects on lipid and leptin concentrations are also shown. The compounds are orally effective anti-diabetic agents that may normalize glucose and lipid metabolism in subjects with diabetes.

  提供了一种口服的新型二苯乙烯化合物，用于降低血液中葡萄糖的浓度。还展示了对胰岛素抵抗的大鼠的影响。同时也展示了对脂质和瘦素浓度的影响。这些化合物是口服有效的抗糖尿病药物，可以在糖尿病患者中使葡萄糖和脂质代谢正常化。
• Anxiolytic Effect of Pterostilbene
  申请人：Rimando Agnes M.

  公开号：US20160067192A1

  公开（公告）日：2016-03-10

  We report for the first time that pterostilbene, a natural analog of resveratrol, shows anxiolytic-like action by downregulating phosphorylated levels of ERKs in the hippocampus of mice. Mice administered pterostilbene (1-10 mg/kg BW) by oral gavage were subjected to the Elevated-plus maze (EPM) test. Pterostilbene manifested anxiolytic activity at 1 and 2 mg/kg doses, demonstrated by an increase in percent permanence time and number of entries in open arms, critical determinants correlated with anxiety. This anxiolytic activity of pterostilbene was comparable to that of diazepam at 1 and 2 mg/kg in the EPM. The percent traveled distance and the percent permanence time in the enclosed arms were decreased with the 1 and 2 mg/kg doses. The 5 and 10 mg/kg doses did not show any anxiolytic effect. Locomotor activity was unaffected in all doses. Western blot analysis corroborated the observed behaviors in the EPM, revealing a decrease in both ERK1 and ERK2 phosphorylation in hippocampal homogenates from mice treated with 1 and 2 mg/kg doses; the 5 and 10 mg/kg doses showed no significant effect on the phosphorylation of ERKs. Pterostilbene was detected in serum and brain tissue following a single oral administration, demonstrating that the compound can cross the blood-brain barrier to reach the brain regions, including hippocampus, and thereby exert its anxiolytic effect. Resveratrol, the parent molecule of pterostilbene, did not have any anxiolytic effect.

  我们首次报告，白藜芦醇的天然类似物白藜苷通过降低小鼠海马区ERKs的磷酸化水平表现出类抗焦虑作用。通过口服给予白藜苷（1-10毫克/千克体重），小鼠接受了提高十字迷宫（EPM）测试。白藜苷在1和2毫克/千克剂量下表现出抗焦虑活性，表现为开放臂停留时间百分比和进入开放臂次数增加，这些是与焦虑相关的关键因素。白藜苷的这种抗焦虑活性与EPM中1和2毫克/千克的地西泮相当。1和2毫克/千克剂量下的封闭臂行程百分比和停留时间百分比减少。5和10毫克/千克剂量没有显示任何抗焦虑效果。所有剂量下的运动活动均未受影响。西方印迹分析证实了EPM中观察到的行为，显示在1和2毫克/千克剂量下，处理后的小鼠海马均匀物中ERK1和ERK2的磷酸化水平降低；5和10毫克/千克剂量对ERKs的磷酸化没有明显影响。通过单次口服给药检测到白藜苷存在于血清和脑组织中，表明该化合物可以穿过血脑屏障到达包括海马在内的脑区域，并发挥其抗焦虑作用。白藜苷的母分子白藜芦醇没有任何抗焦虑效果。
• Anti-Obesity Properties of Pterostilbene
  申请人：Rimando Agnes

  公开号：US20130296441A1

  公开（公告）日：2013-11-07

  We have determined that pterostilbene demonstrates anti-obesity properties. Rats were fed a commercial obesogenic diet supplemented or not with pterostilbene: PT15 (low dose: 15 mg/kg body weight/d) or PT30 (high dose: 30 mg/kg body weight/d) for 6 weeks. Pterostilbene significantly reduced total adipose tissue mass (15.1% in the PT15 group; 22.9% in the PT30 group) without changes in food intake. The activities of lipogenic enzymes were reduced in white adipose tissue and liver. Activities of enzymes involved in liver fatty acid oxidation were significantly increased in the PT30 group. Low dose pterostilbene can reduce body fat by reducing lipogenesis in adipose tissue. At the high dose, two mechanisms contribute to reduction in body fat: (1) decrease in adipose tissue and liver lipogenesis, and (2) an increase in liver fatty acid oxidation.

  我们已经确定白藜芦醇具有抗肥胖特性。大鼠被喂养商业肥胖诱导饮食，其中添加或不添加白藜芦醇：PT15（低剂量：15毫克/千克体重/天）或PT30（高剂量：30毫克/千克体重/天）持续6周。白藜芦醇显著减少了总脂肪组织质量（PT15组减少了15.1％；PT30组减少了22.9％），而食物摄入量没有改变。脂肪生成酶在白色脂肪组织和肝脏中的活性降低。肝脏脂肪酸氧化酶活性在PT30组中显著增加。低剂量白藜芦醇可以通过减少脂肪生成来减少体脂肪。在高剂量下，两种机制有助于减少体脂肪：（1）减少脂肪组织和肝脏脂肪生成，以及（2）增加肝脂肪酸氧化。