tert-butyl ferulate | 62621-21-0

• 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: tert-butyl ferulate
• 英文别名: (E)-tert-Butyl 3-(4-hydroxy-3-methoxyphenyl)acrylate；tert-butyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 62621-21-0
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: SDDYVIXKDZYVJQ-SOFGYWHQSA-N

物化性质

• 沸点：
  366.0±27.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl ferulate 在 4-二甲氨基吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 9.17h， 生成 (R/S)-(E)-3-(4-((2-(1-acetoxypentyl)benzoyl)oxy)phenyl)acrylic acid
  参考文献：
  名称：

  Design and synthesis of the ring-opened derivative of 3-n-butylphthalide-ferulic acid-glucose trihybrids as potential anti-ischemic agents

  摘要：

  To improve aqueous solubility and anti-ischemic activity of 3-n-butylphthalide (NBP), we designed and synthesized the ring-opened derivative of NBP-ferulic acid-glucose trihybrids (S1-S8). These hybrids inhibited adenosine diphosphate (ADP)- or arachidonic acid (AA)-induced platelet aggregation, among them, S2 was 30-fold more water-soluble, and over 10-fold more potent in inhibition of platelet aggregation, as well as reduced ROS generation and protected primary neuronal cells from OGD/R-induced damage, in comparison with NBP. Additionally, S2 was more active than its three moieties alone or in combination, suggesting that the activity of S2 may be attributed to the synergistic effects of these moieties. Importantly, in vivo studies indicated that S2 not only possessed good pharmacokinetic profile, but also improved NBP distribution in rodent brain, suggesting that the glucose moiety in S2 may be recognized by glucose transporter 1 (GLUT1) on blood-brain barrier (BBB), promoting it to penetrate through BBB. Our findings suggest that S2 may be a promising candidate for the intervention of ischemic stroke, warranting further study. (C) 2020 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2020.02.031
• 作为产物：
  描述：

  tert-butyl 4-tert-butoxycarbonyloxy-3-methoxycinnamate 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 以92%的产率得到tert-butyl ferulate
  参考文献：
  名称：

  Base-labile tert-butoxycarbonyl (Boc) group on phenols

  摘要：

  Phenols are deprotected with weak bases from their tert-butoxycarbonyl (Boc) derivatives. Boc deprotection with bases can avoid side reactions during the deprotection with acids. We note the lability of the Boc to bases and are able to utilize it as a new cleavage condition for synthetic studies. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.008

文献信息

• (±)-trans-2-phenyl-2,3-dihydrobenzofurans as leishmanicidal agents: Synthesis, in vitro evaluation and SAR analysis
  作者：Freddy A. Bernal、Marcel Gerhards、Marcel Kaiser、Bernhard Wünsch、Thomas J. Schmidt

  DOI：10.1016/j.ejmech.2020.112493

  日期：2020.11

  (SI > 4.6). Nonetheless, structural optimization as further requirement was inferred from the high clearance of the most potent compound (8m) observed during determination in vitro of its metabolic stability. On the other hand, chiral separation of 8m and subsequent biological evaluation of its enantiomers demonstrated no effect of chirality on activity and cytotoxicity. Holistic analysis of in silico

  利什曼病是由利什曼原虫属的寄生虫引起的一种被忽视的热带病，在世界范围内造成了严重的疾病负担，对数百万人的生命构成了威胁，因此是主要的公共卫生问题。需要更有效且无毒的新疗法，特别是对于内脏利什曼病（一种最严重的疾病）。在二氢苯并呋喃以前具有抗霉菌活性的背景下，我们在此介绍一组70种反式-2-苯基-2,3-二氢苯并呋喃的合成及其对利什曼原虫donovani的体外活性的评估，并讨论结构-活动关系。化合物8m-o和8r表现出最高的效价（IC 50  <2μmol/ L）和抗真菌活性相对于对哺乳动物细胞的细胞毒性的有趣的选择性（SI> 4.6）。尽管如此，从体外代谢测定中观察到的最有效化合物（8m）的高清除率可以推断出结构优化是进一步的要求。另一方面，手性分离8m并随后对其对映异构体进行生物学评估表明，手性对活性和细胞毒性没有影响。通过简单的评分函数估算药物相似性对计算机模拟ADME的性质和配体效率
• Biodegradable Ferulic Acid-Containing Poly(anhydride-ester): Degradation Products with Controlled Release and Sustained Antioxidant Activity
  作者：Michelle A. Ouimet、Jeremy Griffin、Ashley L. Carbone-Howell、Wen-Hsuan Wu、Nicholas D. Stebbins、Rong Di、Kathryn E. Uhrich

  DOI：10.1021/bm3018998

  日期：2013.3.11

  FA-containing biodegradable polymer was prepared via solution polymerization to chemically incorporate FA into a poly(anhydride-ester). The polymer was characterized using nuclear magnetic resonance and infrared spectroscopies. The molecular weight and thermal properties were also determined. In vitro studies demonstrated that the polymer was hydrolytically degradable, thus providing controlled release of the

  阿魏酸 (FA) 是一种抗氧化剂和光保护剂，用于生物医学和化妆品配方中，以预防皮肤癌和衰老。尽管 FA 具有许多健康益处，但导致分解的物理化学不稳定性阻碍了其功效。为了最大限度地减少固有分解，通过溶液聚合将 FA 化学结合到聚（酸酐-酯）中，制备了含 FA 的生物可降解聚合物。使用核磁共振和红外光谱对聚合物进行了表征。还测定了分子量和热性质。体外研究表明，该聚合物可水解降解，从而控制释放化学掺入的生物活性物质，且没有可检测到的分解。研究发现，聚合物降解产物具有与游离 FA 相当的抗氧化和抗菌活性，体外细胞活力研究表明，该聚合物对成纤维细胞无细胞毒性。这使得该聚合物成为用作皮肤护理配方的控释系统的潜在候选者。
• Cinnamic acid derivative, polymer thereof, and liquid crystal alignment layer comprising cured product thereof
  申请人：DIC CORPORATION

  公开号：US10095066B2

  公开（公告）日：2018-10-09

  Provided is a liquid crystal alignment layer of which a constituent member is a compound represented by the general formula (I).

  本发明提供了一种液晶配向层，其组成成分是通式 (I) 所代表的化合物。
• Liquid-crystal display element
  申请人：DIC Corporation

  公开号：US10437107B2

  公开（公告）日：2019-10-08

  An object of the present invention is to provide a liquid-crystal display element using a liquid-crystal composition having negative dielectric anisotropy, capable of realizing excellent display characteristics by being used in a liquid-crystal display element provided with a photo-alignment film, without deteriorating various characteristics as a liquid-crystal display element such as dielectric anisotropy, viscosity, a nematic phase upper limit temperature, nematic phase stability at low temperatures, and γ1, and burn-in characteristics of a display element. A liquid-crystal display element using a liquid-crystal composition containing at least one compound selected from the group consisting of compounds represented by the following General Formula (I) is provided.

  本发明的目的是提供一种使用具有负介电各向异性的液晶组合物的液晶显示元件，该液晶组合物能够通过用于提供光对准膜的液晶显示元件而实现优异的显示特性，同时不会降低作为液晶显示元件的各种特性，例如介电各向异性、粘度、向列相上限温度、向列相在低温下的稳定性和γ1，以及显示元件的烧损特性。本发明提供了一种使用液晶组合物的液晶显示元件，该液晶组合物含有至少一种选自以下通式（I）所代表的化合物组成的化合物组的化合物。
• Design and synthesis of rosiglitazone-ferulic acid-nitric oxide donor trihybrids for improving glucose tolerance
  作者：Jingchao Liu、Zhangjian Huang、Wenhuan Ma、Sixun Peng、Yunman Li、Katrina M. Miranda、Jide Tian、Yihua Zhang

  DOI：10.1016/j.ejmech.2018.10.006

  日期：2019.1

  Glucose intolerance is associated with metabolic syndrome and type 2 diabetes mellitus (T2DM) while some new therapeutic drugs, such as rosiglitazone (Rosi), for T2DM can cause severe cardiovascular side effects. Herein we report the synthesis of Rosi-ferulic acid (FA)-nitric oxide (NO) donor trihybrids to improve glucose tolerance and minimize the side effects. In comparison with Rosi, the most active compound 21 exhibited better effects on improving glucose tolerance, which was associated with its NO production, antioxidant and anti-inflammatory activities. Furthermore, 21 displayed relatively high stability in the simulated gastrointestinal environments and human liver microsomes, and released Rosi in plasma. More importantly, 21, unlike Rosi, had little stimulatory effect on the membrane translocation of aquaporin-2 (AQP2) in kidney collecting duct epithelial cells. These, together with a better safety profile, suggest that the trihybrids, like 21, may be promising candidates for intervention of glucose intolerance-related metabolic syndrome and T2DM. (C) 2018 Published by Elsevier Masson SAS.