tert-butyl 3,4-dihydroxycinnamate | 845883-04-7

• 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 3,4-dihydroxycinnamate
• 英文别名: caffeic acid tert-butyl ester；tert-butyl caffeate；t-butyl caffeate；E-Caffeic acid-T-butyl ester；tert-butyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• CAS: 845883-04-7
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: XPTOEJIWXDVJRT-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2918290000

反应信息

• 作为反应物：
  描述：

  tert-butyl 3,4-dihydroxycinnamate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以26%的产率得到3-(3,4-Dihydroxy-phenyl)-propionic acid tert-butyl ester
  参考文献：
  名称：

  咖啡因和二氢咖啡酸的酯的毒性机理。

  摘要：

  最近已合成了咖啡酸和二氢咖啡酸的十种酯。这些酯对培养中的L1210白血病和MCF-7乳腺癌细胞的细胞毒性评估已导致每个系列的QSAR均存在明显差异。二氢咖啡因酸酯的L1210 QSAR与简单酚和雌激素酚获得的QSAR相似。但是，与咖啡酸酯有关的QSAR与它的姊妹QSAR有很大不同。该差异可以归因于侧链中烯烃键的存在。咖啡酸的辛酯对白血病细胞的毒性是广泛研究的苯乙酯CAPE的十倍。

  DOI：

  10.1016/s0968-0896(00)00238-8
• 作为产物：
  描述：

  异香兰素 在 哌啶 、 吡啶 、 aluminum (III) chloride 作用下， 以 氯仿 为溶剂， 生成 tert-butyl 3,4-dihydroxycinnamate
  参考文献：
  名称：

  Synthesis and antitumor activity of feruloyl and caffeoyl derivatives

  摘要：

  We developed two efficient protocols for the synthesis of feruloyl and caffeoyl derivatives from commercial vanillin and veratraldehyde. Pharmacological activities were assessed against a panel of human cancer cell lines in vitro. Most synthesized compounds demonstrated attractive cytotoxicity. Several new compounds demonstrated significant antiproliferative and cytotoxic activities against HeLa and Bewo tumor cell lines. In particular, 5-nitro caffeic adamantyl ester showed broad spectrum of tumor inhibition in 10 cell lines, and reduced tumor weight by 36.7% in vivo when administered at a dose of 40 mg kg(-1). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.08.024

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
• PAIN RELIEF COMPOUNDS
  申请人：ECOLE NATIONALE SUPERIEURE DE CHIMIE DE CLERMONT FERRAND

  公开号：US20150038466A1

  公开（公告）日：2015-02-05

  The present invention relates to the use of compounds for the treatment or prevention of pain in mammals, in particularly in human beings, and also to a process for preparing these compounds.

  本发明涉及使用化合物治疗或预防哺乳动物（尤其是人类）的疼痛，并且涉及一种制备这些化合物的方法。
• POLYMERIZABLE COMPOUND, AND LIQUID CRYSTAL COMPOSITION PRODUCED USING SAME
  申请人：DIC CORPORATION

  公开号：US20160137921A1

  公开（公告）日：2016-05-19

  The polymerizable composition and the liquid crystal composition containing the polymerizable compound of the present invention have favorable storage stability as evaluated on the basis of the occurrence of precipitation, separation, or the like of crystals during storage. The present invention relates to a polymerizable compound, a liquid crystal composition which contains the compound, and further a liquid crystal display element which contains an optically anisotropic material which is a cured product of the liquid crystal composition, or a cured product which controls alignment of liquid crystal molecules. That is, the present invention relates to a polymerizable compound, and a liquid crystal composition containing the polymerizable compound which contains the polymerizable compound and a liquid crystal compound. The polymerizable compound is a compound represented by General Formula (I), and is useful for an optically anisotropic material, a retardation layer, an alignment film, or a polarizing layer.

  本发明的可聚合组合物和含有该可聚合化合物的液晶组合物在存储期间的晶体沉淀、分离等方面具有良好的稳定性。本发明涉及一种可聚合化合物、包含该化合物的液晶组合物以及进一步包含液晶组合物的光学各向异性材料的固化产物的液晶显示元件，或控制液晶分子取向的固化产物。也就是说，本发明涉及一种可聚合化合物和包含该可聚合化合物的液晶组合物，该可聚合化合物是由通式（I）表示的化合物，可用于光学各向异性材料、减速层、取向膜或偏振层。
• Amide derivatives of polycaffeoylquinic acids, process for producing same and uses thereof
  申请人：TEMISIS

  公开号：US10786690B2

  公开（公告）日：2020-09-29

  The present invention thus relates to amide derivatives of polysubstituted quinic acids (abbreviated to “QPS”), of general formula (IA): (IA), in which —R1A and R2A are, independently of one another: H, with the proviso that R1A and R2A are not both a hydrogen atom, a butyl group, a C7-C30 alkyl group, —a C7-C30 alkylaryl or arylalkyl group, or a C7-C18 aryl group; and —Q1, Q3, Q4 and Q5 are, independently of one another, an OH, caffeoyl, maloyl, caffeoylmaloyl ou maloylcaffeoyl group, with the proviso that at least one of these radicals is not an OH group, or to a pharmaceutically acceptable salt or stereoisomer or hydrate thereof, and also to the process for producing same, to the use thereof as a medicament, in particular for the treatment and/or prevention of inflammation and of inflammatory diseases, and to the pharmaceutical, cosmetic and nutraceutical compositions containing same.

  因此，本发明涉及通式(IA)为(IA)的多取代喹酸（简称 "QPS"）的酰胺衍生物： (IA)，其中-R1A和R2A彼此独立：H，但 R1A 和 R2A 不同时为氢原子、丁基、C7-C30 烷基、-C7-C30 烷芳基或芳烷基或 C7-C18 芳基；Q1、Q3、Q4 和 Q5 相互独立地为 OH、咖啡酰基、丙二酰基、咖啡酰丙二酰基或丙二酰咖啡酰基，但这些基团中至少有一个不是 OH 基，或其药学上可接受的盐或立体异构体或水合物、以及其生产工艺、作为药物的用途，特别是用于治疗和/或预防炎症和炎症性疾病，以及含有该成分的药物、化妆品和营养品组合物。
• Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines
  作者：Chun-nian Xia、Hai-bo Li、Feng liu、Wei-xiao Hu

  DOI：10.1016/j.bmcl.2008.10.046

  日期：2008.12

  Forty caffeate analogues were synthesized via a convenient method starting from vanillin with moderate to good yields. The testing of biological activity of these compounds against HIV-1 integrase indicates that four compounds: bornyl caffeate, bornyl 2-nitrocaffeate, 5-nitrocaffeic acid and 5-nitrocaffeic acid phenethyl ester (5-nitroCAPE) possess a good HIV integrase inhibitory activity, IC50 19.9, 26.8, 25.0 and 13.5 mu M, respectively. Twelve caffeate analogues were tested by MTT assay on growth of human hepatocellular carcinoma BEL-7404, human breast MCF-7 adenocarcinoma, human lung A549 adenocarcinoma and human gastric cancer BCG823 cell lines, respectively. And the best result is IC50 5.5 mu M for CAPE against BEL-7404. (C) 2008 Elsevier Ltd. All rights reserved.