3-acetoxycinnamic acid | 27542-84-3

• 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: 3-acetoxycinnamic acid
• 英文别名: (E)-3-(3-acetyloxyphenyl)prop-2-enoic acid
• CAS: 27542-84-3
• 化学式: C₁₁H₁₀O₄
• 分子量: 206.198
• InChiKey: LSZKRNUEKNCZIE-AATRIKPKSA-N

物化性质

• 沸点：
  373.0±25.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-acetoxycinnamic acid 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 2-(4-(3-acetoxycinnamoyl)-1-piperazinyl)-quinoline
  参考文献：
  名称：

  Synthesis and anticancer activity evaluation of some new derivatives of 2-(4-benzoyl-1-piperazinyl)-quinoline and 2-(4-cinnamoyl-1-piperazinyl)-quinoline.

  摘要：

  In this study, we designed and synthesized twenty new derivatives of 2-(4-benzoyl-1-piperazinyl)quinoline and 2-(4-cinnamoyl-1-piperazinyl)-quinoline with potential anticancer activity. The structures of synthesized compounds were confirmed by H-1 and C-13 NMR spectroscopy and MS spectrometry. The activity of novel compounds was evaluated in the cell viability assay as well as in the wound healing assay. Presented data show that examined substances have anticancer activity in cell culture. Seven compounds which showed a high rate of cell growth inhibition were selected for further studies. Three of them strongly reduced the growth of B16F10 cells. The novel compounds constitute a good base for further studies and optimization of structure for new therapeutically effective anti-cancerous drugs.

  DOI：

  10.32383/appdr/80098
• 作为产物：
  描述：

  间羟基苯甲醛 在 吡啶 作用下， 反应 4.0h， 生成 3-acetoxycinnamic acid
  参考文献：
  名称：

  Design and synthesis optimization of novel diimide indoles derivatives for ameliorating acute lung injury through modulation of NF-κB signaling pathway

  摘要：

  DOI：

  10.1016/j.bioorg.2023.106557

文献信息

• AMINO ACID DERIVATIVE
  申请人：Ookubo Tomohiro

  公开号：US20110172442A1

  公开（公告）日：2011-07-14

  The amino acid derivative of the present invention provides a novel compound that shows excellent analgesic action. The amino acid derivative of the present invention is a novel compound that shows excellent analgesic action to not only a model animal for nociceptive pains but also a model animal for neuropathic pains, so that the amino acid derivative is very useful as a drug for treating various pain diseases.

  本发明的氨基酸衍生物提供了一种显示出优异镇痛作用的新化合物。本发明的氨基酸衍生物是一种新化合物，不仅对于模拟伤害性疼痛的动物模型，而且对于模拟神经病理性疼痛的动物模型都显示出优异的镇痛作用，因此该氨基酸衍生物作为治疗各种疼痛疾病的药物非常有用。
• Iron-catalyzed direct alkenylation of sp3(C–H) bonds via decarboxylation of cinnamic acids under ligand-free conditions
  作者：Hailong Yang、Hong Yan、Peng Sun、Yan Zhu、Linhua Lu、Defu Liu、Guangwei Rong、Jincheng Mao

  DOI：10.1039/c3gc37131j

  日期：——

  An example of highly efficient low-cost ferrocene-catalyzed decarboxylative C(sp2)–C(sp3) coupling reactions via C–H functionalization has been developed successfully. It is noteworthy that nanoparticles of Fe3O4 could be used as a reusable catalyst for 7 times in the absence of ligand.

  成功开发了一种高效低成本的二茂铁催化通过C-H官能化实现的脱羧C(sp²)-C(sp³)偶联反应的实例。值得注意的是，在没有配体的情况下，Fe₃O₄纳米颗粒可用作可重复使用的催化剂，连续使用七次。
• Examination of α-exosite inhibitors against Botulinum neurotoxin A protease through structure-activity relationship studies of chicoric acid
  作者：Song Xue、Hajime Seki、Marek Remes、Peter Šilhár、Kim Janda

  DOI：10.1016/j.bmcl.2017.10.021

  日期：2017.11

  Chicoric acid (ChA) was previously reported as a BoNT/A inhibitor that binds to the enzyme’s α-exosite. Herein, we report the synthesis and structure-activity relationships (SARs) of a series of ChA derivatives, which revealed essential binding interactions between ChA and BoNT/A. Moreover, several ChA-based inhibitors with improved potency against the BoNT/A were discovered.

  肉毒杆菌神经毒素 (BoNT) 是已知毒性最强的物质之一，目前尚无针对神经元内 BoNT 中毒的有效治疗方法。菊苣酸 (ChA) 先前被报道为一种 BoNT/A 抑制剂，可与该酶的 α-外部位点结合。在此，我们报告了一系列 ChA 衍生物的合成和构效关系 (SAR)，揭示了 ChA 和 BoNT/A 之间的重要结合相互作用。此外，还发现了几种基于 ChA 的抑制剂，其对抗 BoNT/A 的效力有所提高。
• Extensive Structure Modification on Luteolin-Cinnamic Acid Conjugates Leading to BACE1 Inhibitors with Optimal Pharmacological Properties
  作者：De-Yang Sun、Chen Cheng、Katrin Moschke、Jian Huang、Wei-Shuo Fang

  DOI：10.3390/molecules25010102

  日期：——

  BACE1 inhibitory conjugates derived from two natural products, luteolin (1) and p-hydroxy-cinnamic acid (2), were subjected to systematic structure modifications, including various positions in luteolin segment for conjugation, different linkers (length, bond variation), as well as various substitutions in cinnamic acid segment (various substituents on benzene, and replacement of benzene by heteroaromatics

  来自两种天然产物木犀草素 (1) 和对羟基肉桂酸 (2) 的 BACE1 抑制缀合物经过系统结构修饰，包括木犀草素片段中的不同位置进行缀合、不同的接头（长度、键变异），如以及肉桂酸片段中的各种取代（苯上的各种取代基，以及用杂芳烃和环烷烃取代苯）。根据一系列生物测定数据选择最佳偶联物，如 7c 和 7k，以进行进一步研究。
• Design and synthesis novel di-carbonyl analogs of curcumin (DACs) act as potent anti-inflammatory agents against LPS-induced acute lung injury (ALI)
  作者：Jianchang Qian、Xianxin Chen、Sheng Shu、Wenxin Zhang、Bo Fang、Xiaojing Chen、Yunjie Zhao、Zhiguo Liu、Guang Liang

  DOI：10.1016/j.ejmech.2019.02.042

  日期：2019.4

  A novel series of di-carbonyl analogs of curcumin (DACs) were prepared and evaluated for their anti-inflammatory properties. Preliminary results showed that a vast majority of compounds tested in this study could effectively suppress LPS-induced production of tumor necrosis factor (TNF)-α and interleukin (IL)-6. Structure-activity relationships of the compounds were discussed. Compounds 5a27 and 5a28

  制备了一系列新的姜黄素二羰基类似物（DACs），并评估了它们的抗炎特性。初步结果表明，本研究中测试的绝大多数化合物都可以有效抑制LPS诱导的肿瘤坏死因子（TNF）-α和白介素（IL）-6的产生。讨论了化合物的构效关系。化合物5a27和5a28显示出最有效的抗炎活性和具有比姜黄素更高的结构稳定性和生物利用度口服体外。从机制上讲，它们通过抑制有丝分裂原激活的蛋白激酶（MAPK）信号传导和NF-κB的核易位来抑制巨噬细胞的激活。在体内，5a275a28和5a28可以显着减轻脂多糖（LPS）诱导的急性肺损伤（ALI）。活性化合物使肺的干/湿比显着标准化，这与中性粒细胞浸润的抑制和促炎性细胞因子的产生是一致的。总的来说，这些结果提出了一系列新的姜黄素类似物，作为有望用于治疗ALI的抗炎药。

表征谱图