1-(2-甲氧基-4-(四氢-2H-吡喃-2-氧基)苯基)乙酮 | 288856-48-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-甲氧基-4-(四氢-2H-吡喃-2-氧基)苯基)乙酮
• 英文名称: 1-(2-methoxy-4-(tetrahydro-2H-pyran-2-yloxy)phenyl)ethanone
• 英文别名: 1-(2-Methoxy-4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)ethan-1-one；1-[2-methoxy-4-(oxan-2-yloxy)phenyl]ethanone
• CAS: 288856-48-4
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: NKMBNLCPLCCFDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-吡啶甲醛 、 1-(2-甲氧基-4-(四氢-2H-吡喃-2-氧基)苯基)乙酮 在 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.5h， 以12.9%的产率得到(E)-1-(4-hydroxy-2-methoxyphenyl)-3-(pyridin-4-yl)prop-2-en-1-one
  参考文献：
  名称：

  Chalcones as Novel Non-peptidic μ-Calpain Inhibitors

  摘要：

  为了扩展非肽类钙蛋白酶抑制剂的支架，我们设计并合成了14种查耳酮衍生物，根据其结构分为两类。化合物 7 ($IC_{50}=16.67{\pm}0.42{\mu}M$) 和 8 ($IC_{50}=16.92{\pm}0.14{\mu A 组中的 }M$) 是比组织蛋白酶 B 和 L 最具选择性的 ${\mu}$-钙蛋白酶抑制剂。 另一方面，具有呋喃环的化合物 14 对${\mu}$-钙蛋白酶 ($IC_{50}=15.39{\pm}1.34{\mu}M$) 以及组织蛋白酶 B ($IC_{50}=20.59{\pm}1.35{\mu}M$)。研究结果表明，具有适当大小和官能团的查尔酮类似物可以成为选择性非肽${\mu}$-钙蛋白酶抑制剂的潜在先导核心。此外，${\mu}$-calpain 和组织蛋白酶 B 的双重抑制剂也可以通过精细的结构操作从查耳酮中开发出来。

  DOI：

  10.5012/bkcs.2011.32.9.3459

文献信息

• Neuroprotective effect of synthetic chalcone derivatives as competitive dual inhibitors against μ-calpain and cathepsin B through the downregulation of tau phosphorylation and insoluble Aβ peptide formation
  作者：Kyung-Hwa Jeon、Eunyoung Lee、Kyu-Yeon Jun、Ji-Eun Eom、Soo Yeon Kwak、Younghwa Na、Youngjoo Kwon

  DOI：10.1016/j.ejmech.2016.06.008

  日期：2016.10

  A series of chalcone derivatives were synthesized and evaluated for their μ-calpain and cathepsin B inhibitory activities. Among the tested chalcone derivatives, two compounds, 7 and 11, showed potent inhibitory activities against μ-calpain and cathepsin B and were selected for further evaluation. Compounds 7 and 11 showed enzyme inhibitory activities at the cellular level and displayed neuroprotective

  合成了一系列查尔酮衍生物，并评估了它们的μ-钙蛋白酶和组织蛋白酶B抑制活性。在测试的查耳酮衍生物中，两种化合物7和11显示出对μ-钙蛋白酶和组织蛋白酶B的有效抑制活性，因此选择进行进一步评估。化合物7和11在人的神经母细胞瘤细胞系SH-SY5Y细胞中显示出在细胞水平上的酶抑制活性，并显示出对氧化应激诱导的细胞凋亡的神经保护作用。此外，化合物7和11减少了p25的形成，tau磷酸化和不溶性Aβ肽的形成。酶动力学实验和对接研究表明，这些化合物7和11竞争性抑制μ-钙蛋白酶和组织蛋白酶B酶。
• 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.