(E)-1-(4-fluorophenyl)-3-(4-hydroxy-2-methoxyphenyl)prop-2-en-1-one | 1437743-11-7

• 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: (E)-1-(4-fluorophenyl)-3-(4-hydroxy-2-methoxyphenyl)prop-2-en-1-one
• CAS: 1437743-11-7
• 化学式: C₁₆H₁₃FO₃
• 分子量: 272.276
• InChiKey: ORZOHKUZXRJGEK-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 以 乙醇 为溶剂， 生成 (E)-1-(4-fluorophenyl)-3-(4-hydroxy-2-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Chalcones, inhibitors for topoisomerase I and cathepsin B and L, as potential anti-cancer agents

  摘要：

  In order to diversify the pharmacological activity of chalcones and extend the scaffold of topoisomerase and cathepsins B and L inhibitors, we have designed and synthesized total 18 chalcone compounds and tested their biological activity. In the topoisomerase inhibition test, most analogues in group III and IV except compound 11 exhibited more efficient topoisomerase I inhibitory activity than camptothecin at 20 lM. Compounds 15, 16 and 18 in group IV showed significant cathepsin B and L inhibitory activity. Among the compounds, compound 15 was most active with IC50 values of 1.81 +/- 0.05 mu M on cathepsin B and 3.15 +/- 0.07 mu M on cathepsin L, respectively. Compound 15 also showed most potent cytotoxic activity against T47D and SNU638 cells with IC50 values of 1.37 +/- 0.05 mu M and 0.62 +/- 0.01 mu M, respectively. Overall, although more compounds should be tested and analyzed for clear SAR against topoisomerase I and cathepsin B and L, compound 15 showed consistent inhibitory ability on the tested assays, which can implicate the cytotoxic activity of compound 15 on topoisomerase I and cathepsin B and L inhibitory pathways. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.106

文献信息

• Insights into the molecular basis of some chalcone analogues as potential inhibitors of <i>Leishmania donovani:</i> An integrated <i>in silico</i> and <i>in vitro</i> study
  作者：Marwa S. Osman、Talal A. Awad、Shaza W. Shantier、Elrashied A. E. Garelnabi、Moawia M. Mukhtar、Wadah Osman、Ramzi A. Mothana、Rashid I. Elhag

  DOI：10.1515/chem-2022-0160

  日期：2022.7.18

  work highlights the synthesis of some chalcones to be used as potential anti-leishmanial agents. The activity of the synthesized chalcones has been evaluated against L. donovani. The ADMET profile of the synthesized compounds were tested using various integrated web-based tools. Moreover, in order to investigate the molecular mechanism of action, the chalcone compounds were docked into L. donovani trypanothione

  由属于的物种引起的原虫感染多诺瓦尼利什曼原虫复杂的利什曼病是最严重的形式，特别是在苏丹和其他发展中国家。通常用于治疗该疾病的药物显示出不同程度的有效性，并且还具有相关的副作用。因此，目前的工作强调了一些查尔酮的合成，这些查尔酮可用作潜在的抗利什曼原虫剂。合成的查耳酮的活性已针对大号.多诺瓦尼. 使用各种基于网络的集成工具测试了合成化合物的 ADMET 谱。此外，为了研究分子作用机制，将查尔酮类化合物对接大号.多诺瓦尼使用 Autodock 4.0 和分子动力学研究了锥虫硫酮还原酶 (TR)。八种化合物对形态形式表现出最高的活性。在这些化合物中，查尔酮 15 对 IC 的抑制作用最强50值为 1.1 µM。此外，药代动力学和毒理学研究表明其具有良好的口服生物利用度和低毒性。此外，查尔酮 15 被发现与 TR 具有高亲和力（-13.7 kcal/mol），TR 是利什曼寄生虫的必需酶。因此，这项有希望的活动针对大号
• Chalcones, inhibitors for topoisomerase I and cathepsin B and L, as potential anti-cancer agents
  作者：Seok-Ho Kim、Eunyoung Lee、Kyung Hye Baek、Han Byeol Kwon、Hyunjung Woo、Eung-Seok Lee、Youngjoo Kwon、Younghwa Na

  DOI：10.1016/j.bmcl.2013.03.106

  日期：2013.6

  In order to diversify the pharmacological activity of chalcones and extend the scaffold of topoisomerase and cathepsins B and L inhibitors, we have designed and synthesized total 18 chalcone compounds and tested their biological activity. In the topoisomerase inhibition test, most analogues in group III and IV except compound 11 exhibited more efficient topoisomerase I inhibitory activity than camptothecin at 20 lM. Compounds 15, 16 and 18 in group IV showed significant cathepsin B and L inhibitory activity. Among the compounds, compound 15 was most active with IC50 values of 1.81 +/- 0.05 mu M on cathepsin B and 3.15 +/- 0.07 mu M on cathepsin L, respectively. Compound 15 also showed most potent cytotoxic activity against T47D and SNU638 cells with IC50 values of 1.37 +/- 0.05 mu M and 0.62 +/- 0.01 mu M, respectively. Overall, although more compounds should be tested and analyzed for clear SAR against topoisomerase I and cathepsin B and L, compound 15 showed consistent inhibitory ability on the tested assays, which can implicate the cytotoxic activity of compound 15 on topoisomerase I and cathepsin B and L inhibitory pathways. (C) 2013 Elsevier Ltd. All rights reserved.