{4-[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]phenoxy}acetic acid | 70765-80-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: {4-[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]phenoxy}acetic acid
• 英文别名: 2-[4-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]phenoxy]acetic Acid
• CAS: 70765-80-9
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: BUSXGJRHXAAYLC-NYYWCZLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  {4-[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]phenoxy}acetic acid 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis of a series of novel dihydroartemisinin derivatives containing a substituted chalcone with greater cytotoxic effects in leukemia cells

  摘要：

  Fifteen dihydroartemisinin derivatives containing a substituted chalcone linked by either ether or ester were synthesized and investigated for their cytotoxicity in human leukemia HL-60 and mouse lymphoma P388 cells. These derivatives have greater antiproliferative and cytotoxic effects in both cell lines than dihydroartemisinin. Dihydroartemisinin chalcones linked by ether are more cytotoxic than dihydroartemisinin chalcones linked by ester with apoptosis induction abilities. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.076
• 作为产物：
  描述：

  ethyl 2-[4-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]phenoxy]acetate 在 sodium hydroxide 、 盐酸 、 水 作用下， 反应 1.0h， 生成 {4-[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]phenoxy}acetic acid
  参考文献：
  名称：

  Synthesis of a series of novel dihydroartemisinin derivatives containing a substituted chalcone with greater cytotoxic effects in leukemia cells

  摘要：

  Fifteen dihydroartemisinin derivatives containing a substituted chalcone linked by either ether or ester were synthesized and investigated for their cytotoxicity in human leukemia HL-60 and mouse lymphoma P388 cells. These derivatives have greater antiproliferative and cytotoxic effects in both cell lines than dihydroartemisinin. Dihydroartemisinin chalcones linked by ether are more cytotoxic than dihydroartemisinin chalcones linked by ester with apoptosis induction abilities. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.076

文献信息

• Novel chalcone/aryl carboximidamide hybrids as potent anti-inflammatory via inhibition of prostaglandin E2 and inducible NO synthase activities: design, synthesis, molecular docking studies and ADMET prediction
  作者：Tarek S. Ibrahim、Amr H. Moustafa、Ahmad J. Almalki、Rasha M. Allam、Abdulhamid Althagafi、Shadab Md、Mamdouh F. A. Mohamed

  DOI：10.1080/14756366.2021.1929201

  日期：2021.1.1

  Abstract Two series of chalcone/aryl carboximidamide hybrids 4a–f and 6a–f were synthesised and evaluated for their inhibitory activity against iNOS and PGE2. The most potent derivatives were further checked for their in vivo anti-inflammatory activity utilising carrageenan-induced rat paw oedema model. Compounds 4c, 4d, 6c and 6d were proved to be the most effective inhibitors of PGE2, LPS-induced

   抽象的 合成了两个系列的查耳酮/芳基甲脒酰胺杂化物4a-f和6a-f ，并评估了它们对 iNOS 和 PGE2 的抑制活性。利用角叉菜胶诱导的大鼠爪水肿模型进一步检查了最有效的衍生物的体内抗炎活性。化合物4c 、 4d 、 6c和6d被证明是PGE2、LPS诱导的NO产生、iNOS活性最有效的抑制剂。此外，与吲哚美辛（56.27±2.14%）和塞来昔布（12.32%）相比， 4c 、 4d 、 6c和6d显示出显着的水肿抑制作用，范围为62.21%至78.51%。此外， 4c 、 6a和6e表现出良好的COX2抑制活性，而4c 、 6a和6c表现出最高的5LOX抑制活性。化合物4c 、 4d 、 6c和6d通过重要的氨基酸残基很好地融入 iNOS 蛋白（PDB ID：1r35）的口袋中。理化参数预测表明4c 、 4d 、 6c和6d具有可接受的理化参数和药物相似性。结果表明，查耳酮/芳基甲脒酰胺4c
• 10.1016/j.bioorg.2024.107727
  作者：Elgohary, Mohamed K.、Abo-Ashour, Mahmoud F.、Abd El Hadi, Soha R.、El Hassab, Mahmoud A.、Abo-El Fetoh, Mohammed E.、Afify, Hassan、Abdel-Aziz, Hatem A.、Abou-Seri, Sahar M.

  DOI：10.1016/j.bioorg.2024.107727

  日期：——

  compounds, and emerged as promising candidates, demonstrating potent COX-2 inhibition with IC values of 0.03 µM for both and selectivity index = 365.4 and 196.9, respectively. Furthermore, these compounds exhibited efficacy in mitigating formalin-induced edema in male Wistar rats, accompanied by favorable safety profiles upon histological examination of vital organs. Comprehensive safety assessments, including

  炎症管理对现代医学提出了严峻的挑战，非甾体抗炎药（NSAID）是一种广泛使用的治疗选择。然而，它们的功效往往伴随着显着的胃肠道副作用，因此需要探索更安全的替代品，特别是通过环氧合酶-2 (COX-2) 抑制剂的研究。本研究致力于通过吡唑啉-苯氧基乙酸衍生物的合成和评估来解决这一迫切问题。在合成的化合物中， 和 成为有前途的候选化合物，表现出有效的 COX-2 抑制作用，两者的 IC 值为 0.03 µM，选择性指数分别为 365.4 和 196.9。此外，这些化合物在减轻雄性 Wistar 大鼠福尔马林诱导的水肿方面表现出功效，并且在重要器官的组织学检查中具有良好的安全性。全面的安全性评估，包括肌酐、AST 和 ALT 酶以及肌钙蛋白 T 和肌酸激酶 MB 水平的评估，进一步强化了合成候选物的有前途的属性。分子动力学模拟认可的分子对接研究证实了生物学发现，阐明了 COX-2 活性位点上显着
• Novel 1,2,4-oxadiazole-chalcone/oxime hybrids as potential antibacterial DNA gyrase inhibitors: Design, synthesis, ADMET prediction and molecular docking study
  作者：Tarek S. Ibrahim、Ahmad J. Almalki、Amr H. Moustafa、Rasha M. Allam、Gamal El-Din A. Abuo-Rahma、Hussein I. El Subbagh、Mamdouh F.A. Mohamed

  DOI：10.1016/j.bioorg.2021.104885

  日期：2021.6
• Synthesis of a series of novel dihydroartemisinin derivatives containing a substituted chalcone with greater cytotoxic effects in leukemia cells
  作者：Xuelin Yang、Wei Wang、Jun Tan、Dandan Song、Ming Li、Dan Liu、Yongkui Jing、Linxiang Zhao

  DOI：10.1016/j.bmcl.2009.05.076

  日期：2009.8

  Fifteen dihydroartemisinin derivatives containing a substituted chalcone linked by either ether or ester were synthesized and investigated for their cytotoxicity in human leukemia HL-60 and mouse lymphoma P388 cells. These derivatives have greater antiproliferative and cytotoxic effects in both cell lines than dihydroartemisinin. Dihydroartemisinin chalcones linked by ether are more cytotoxic than dihydroartemisinin chalcones linked by ester with apoptosis induction abilities. (C) 2009 Elsevier Ltd. All rights reserved.