(E)-1-(2,4-Dihydroxyphenyl)-3-(4-pyrrolidin-1-ylphenyl)prop-2-en-1-one | 1437743-49-1

• 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-(2,4-Dihydroxyphenyl)-3-(4-pyrrolidin-1-ylphenyl)prop-2-en-1-one
• 英文别名: (E)-1-(2,4-dihydroxyphenyl)-3-(4-pyrrolidin-1-ylphenyl)prop-2-en-1-one
• CAS: 1437743-49-1
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: QTFHMBIGUFBINV-BJMVGYQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-吡咯烷羰酰氯 、 (E)-1-(2,4-Dihydroxyphenyl)-3-(4-pyrrolidin-1-ylphenyl)prop-2-en-1-one 在 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 以56.9%的产率得到(E)-3-hydroxy-4-(3-(4-(pyrrolidin-1-yl)phenyl)acryloyl)phenyl pyrrolidine-1-carboxylate
  参考文献：
  名称：

  4'-氨基查尔酮-卡斯汀明杂种作为多功能药物治疗阿尔茨海默氏病的设计，合成和生物学评估

  摘要：

  设计，合成和评估了一系列4'-氨基查尔酮-雷伐他明杂种，作为治疗阿尔茨海默氏病的多功能药物。结果表明，大多数这些化合物表现出良好的多功能活性。特别地，化合物6c对乙酰胆碱酯酶表现出最佳的抑制效能（IC 50  = 4.91μM），并且具有显着的抗氧化活性，其值为Trolox的2.83倍。AChE抑制的动力学分析表明，6c显示出混合型抑制，同时与AChE的催化活性位点和外围阴离子位点结合。此外，6C抑制自感应的β 1-42聚集和Cu 2+诱导的阿β 1-42聚合由89.5％，并在25μM分别79.7％，以及充当选择性单胺氧化酶B抑制剂（IC 50  = 0.29μM）和选择性biometal螯合剂。此外，6c可以在体外穿过血脑屏障。根据这些结果，化合物6c可以被认为是阿尔茨海默氏病非常有前途的先导化合物。

  DOI：

  10.1016/j.bmc.2016.12.013
• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 以 乙醇 为溶剂， 生成 (E)-1-(2,4-Dihydroxyphenyl)-3-(4-pyrrolidin-1-ylphenyl)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

• Design, synthesis and biological evaluation of 4′-aminochalcone-rivastigmine hybrids as multifunctional agents for the treatment of Alzheimer's disease
  作者：Ganyuan Xiao、Yan Li、Xiaoming Qiang、Rui Xu、Yunxiaozhu Zheng、Zhongcheng Cao、Li Luo、Xia Yang、Zhipei Sang、Fu Su、Yong Deng

  DOI：10.1016/j.bmc.2016.12.013

  日期：2017.2

  A series of 4′-aminochalcone-revastigmine hybrids were designed, synthesized and evaluated as multifunctional agents for the treatment of Alzheimer’s disease. The results showed that most of these compounds exhibited good multifunctional activities. In particular, compound 6c displayed the best inhibitory potency on acetylcholinesterase (IC50 = 4.91 μM), and significant antioxidative activity with

  设计，合成和评估了一系列4'-氨基查尔酮-雷伐他明杂种，作为治疗阿尔茨海默氏病的多功能药物。结果表明，大多数这些化合物表现出良好的多功能活性。特别地，化合物6c对乙酰胆碱酯酶表现出最佳的抑制效能（IC 50  = 4.91μM），并且具有显着的抗氧化活性，其值为Trolox的2.83倍。AChE抑制的动力学分析表明，6c显示出混合型抑制，同时与AChE的催化活性位点和外围阴离子位点结合。此外，6C抑制自感应的β 1-42聚集和Cu 2+诱导的阿β 1-42聚合由89.5％，并在25μM分别79.7％，以及充当选择性单胺氧化酶B抑制剂（IC 50  = 0.29μM）和选择性biometal螯合剂。此外，6c可以在体外穿过血脑屏障。根据这些结果，化合物6c可以被认为是阿尔茨海默氏病非常有前途的先导化合物。
• 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.