(E)-3-(3,4-dimethoxyphenyl)acrylohydrazide | 88368-69-8

• 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: (E)-3-(3,4-dimethoxyphenyl)acrylohydrazide
• 英文别名: (2E)-3-(3,4-dimethoxyphenyl)acrylohydrazide；(E)-3-(3,4-dimethoxyphenyl)prop-2-enehydrazide
• CAS: 88368-69-8
• 化学式: C₁₁H₁₄N₂O₃
• 分子量: 222.244
• InChiKey: DFDYATFYDWUYGY-GQCTYLIASA-N

物化性质

• 熔点：
  210-213 °C
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  73.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(3,4-dimethoxyphenyl)acrylohydrazide 在 三溴化硼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.42h， 生成 5-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-1,3,4-oxadiazol-2(3H)-one
  参考文献：
  名称：

  Resveratrol-Based MTDLs to Stimulate Defensive and Regenerative Pathways and Block Early Events in Neurodegenerative Cascades

  摘要：

  DOI：

  10.1021/acs.jmedchem.1c01883
• 作为产物：
  描述：

  3,4-二甲氧基肉桂酰氯 在 hydrazine hydrate 作用下， 以 乙腈 为溶剂， 生成 (E)-3-(3,4-dimethoxyphenyl)acrylohydrazide
  参考文献：
  名称：

  Synthesis of piplartine analogs and preliminary findings on structure–antimicrobial activity relationship

  摘要：

  In this work it is described the synthesis, characterization and antimicrobial and toxicity evaluation of a series of analogs of piplartine, a piperamide found in Piper sp. The compounds structures were confirmed by infrared spectroscopy, H-1, C-13 nuclear magnetic resonance, high resolution mass spectroscopy and were evaluated against strains of Candida spp., Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. Derivative 24 was almost four-fold more potent (IC50: 48.83 mu M) and five-fold less toxic (SI > 3) than piplartine (IC50: 189.2 mu M; SI: 0.21) against Candida krusei, as well as two-fold more potent than fluconazole (IC50: 104.48 mu M). This compound was also active against Candida tropicalis at 97.67 mu M. Benzoyl derivative 17 was three-fold more potent (IC50: 85.2 mu M) and more than five-fold less toxic (CC50: 231.71 mu M) than piplartine (IC50: 315.33 mu M and CC50: 41.14 mu M) against Staphylococcus aureus. Given these findings, we have found analogs of piplartine which can be assumed as prototypes for the optimization and the development of new antimicrobial (compounds 24 and 17) agents.

  DOI：

  10.1007/s00044-016-1774-9

文献信息

• Cinnamoyl-N-Acylhydrazone-Donepezil Hybrids: Synthesis and Evaluation of Novel Multifunctional Ligands Against Neurodegenerative Diseases
  作者：Cindy Juliet Cristancho Ortiz、Caio Miranda Damasio、Letizia Pruccoli、Nathália Fonseca Nadur、Luciana Luiza de Azevedo、Isabella Alvim Guedes、Laurent Emmanuel Dardenne、Arthur Eugen Kümmerle、Andrea Tarozzi、Claudio Viegas

  DOI：10.1007/s11064-020-03148-2

  日期：2020.12

  Abstract A new series of ten multifunctional Cinnamoyl-N-acylhydrazone-donepezil hybrids was synthesized and evaluated as multifunctional ligands against neurodegenerative diseases. The molecular hybridization approach was based on the combination of 1-benzyl-4-piperidine fragment from the anti-Alzheimer AChE inhibitor donepezil (1) and the cinnamoyl subunit from curcumin (2), a natural product with

  摘要 合成了一系列新的十个多功能肉桂酸-N-酰基ep-多奈哌齐杂种，并将其评价为对抗神经变性疾病的多功能配体。分子杂交方法基于抗阿尔茨海默氏病AChE抑制剂多奈哌齐（1）的1-苄基-4-哌啶片段和姜黄素（2）的肉桂酰亚基的组合，姜黄素是具有显着抗氧化剂，神经保护和抗衰老作用的天然产物。N-酰基hydr片段作为间隔子亚基，具有炎性特性。化合物4a和4d对AChE表现出中等抑制作用，IC 50值分别为13.04和9.1 µM。另外，复合图4a和4d显示了与在分子对接研究中观察到的多奈哌齐相似的预测结合模式。另一方面，化合物4a和4c表现出显着的自由基清除活性，对DPPH测试显示出最佳效果，并且还表现出显着的保护性神经元细胞活力，其暴露于t-BuOOH和针对6-OHDA的损伤可防止帕金森氏病的氧化应激疾病。类似地，化合物4c能够防止ROS形成，间接的抗氧化剂活性增加了细胞内GSH水平，并且具有抵
• NEW GUANIDINE DERIVATIVES IN CINNAMIC SERIES
  申请人：Rault Sylvain

  公开号：US20130165507A1

  公开（公告）日：2013-06-27

  The invention relates to novel guanidine derivatives in the cinnamic series of general formula (I): The invention also relates to the process for preparing said guanidine derivatives and also to synthetic intermediates. Finally, the invention relates to the use of the guanidine derivatives for the preparation of compositions with anti-glycation properties, especially in cosmetology.

  本发明涉及一种新型的肉桂酸系列的胍衍生物，其通式为（I）：本发明还涉及制备上述胍衍生物的方法以及合成中间体。最后，本发明涉及使用这种胍衍生物制备具有抗糖化性质的组合物，特别是在化妆品中的应用。
• Synthesis, antiviral activity, and molecular docking study of trans-ferulic acid derivatives containing acylhydrazone moiety
  作者：Zhenzhen Wang、Dandan Xie、Xiuhai Gan、Song Zeng、Awei Zhang、Limin Yin、Baoan Song、Linhong Jin、Deyu Hu

  DOI：10.1016/j.bmcl.2017.07.038

  日期：2017.9

  In this study, we report the synthesis and antiviral activity of trans-ferulic acid derivatives containing acylhydrazone moiety. Biological tests demonstrated that most target compounds showed potent antiviral activity against tobacco mosaic virus (TMV). Compound D4 showed remarkable inactivating activity with EC50 value of 36.59 μg/mL, which was obviously superior to ribavirin (126.05 μg/mL). Molecular

  在这项研究中，我们报告了含有酰基hydr部分的反式阿魏酸衍生物的合成和抗病毒活性。生物学测试表明，大多数目标化合物均显示出对烟草花叶病毒（TMV）的有效抗病毒活性。化合物D4表现出显着的灭活活性，EC 50值为36.59μg/ mL，明显优于利巴韦林（126.05μg/ mL）。分子对接结果表明，化合物D4具有与TMV外壳蛋白（TMV-CP）的不同氨基酸残基的五个氢键的最佳结合能力。对接的结果与目标化合物对TMV的灭活活性是一致的。
• Design and synthesis of new (E)-cinnamic N-acylhydrazones as potent antitrypanosomal agents
  作者：Samir A. Carvalho、Larisse O. Feitosa、Márcio Soares、Thadeu E.M.M. Costa、Maria G. Henriques、Kelly Salomão、Solange L. de Castro、Marcel Kaiser、Reto Brun、James L. Wardell、Solange M.S.V. Wardell、Gustavo H.G. Trossini、Adriano D. Andricopulo、Edson F. da Silva、Carlos A.M. Fraga

  DOI：10.1016/j.ejmech.2012.05.041

  日期：2012.8

  We report herein the synthesis and trypanocidal profile of new (E)-cinnamic N-acylhydrazones (NAHs) designed by exploiting molecular hybridization between the potent cruzain inhibitors (E)-1-(benzo[d] 11,3)dioxol-5-yl)-3-(4-bromophenyl)prop-2-en-1-one and (E)-3-hydroxy-N'-((2-hydroxynaphthalen-1-yl)methylene)-7-methoxy-2-naphthohydrazide. These derivatives were evaluated against both amastigote and trypomastigote forms of Trypanosoma cruzi and lead us to identify two compounds that were approximately two times more active than the reference drug, benznidazole, and with good cytotoxic index. Although designed as cruzain inhibitors, the weak potency displayed by the best cinnamyl NAH derivatives indicated that another mechanism of action was likely responsible for their trypanocide action. (C) 2012 Elsevier Masson SAS. All rights reserved.
• TANAKA, KUNIYOSHI;MATSUO, KEIZO;NAKANISHI, AI;HATANO, TOSHIKO;IZEKI, HISA+, CHEM. AND PHARM. BULL., 1983, 31, N 8, 2810-2819
  作者：TANAKA, KUNIYOSHI、MATSUO, KEIZO、NAKANISHI, AI、HATANO, TOSHIKO、IZEKI, HISA+

  DOI：——

  日期：——