(E)-1-(2-hydroxy-4-methoxy-5-(morpholinomethyl)phenyl)-3-phenylprop-2-en-1-one | 1060172-17-9

• 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: (E)-1-(2-hydroxy-4-methoxy-5-(morpholinomethyl)phenyl)-3-phenylprop-2-en-1-one
• 英文别名: (E)-1-(2-Hydroxy-4-methoxy-5-(morpholinomethyl)-phenyl)-3-phenylprop-2-en-1-one；(E)-1-[2-hydroxy-4-methoxy-5-(morpholin-4-ylmethyl)phenyl]-3-phenylprop-2-en-1-one
• CAS: 1060172-17-9
• 化学式: C₂₁H₂₃NO₄
• 分子量: 353.418
• InChiKey: WDAHOVVHQOJONN-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-[4-methoxy-2-hydroxy-5-(morpholinomethyl)phenyl]ethanone 、 苯甲醛 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以73%的产率得到(E)-1-(2-hydroxy-4-methoxy-5-(morpholinomethyl)phenyl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of Mannich bases of heterocyclic chalcone analogs as cytotoxic agents

  摘要：

  The chalcone skeleton (1,3-diphenyl-2-propen-1-one) is a unique template that is associated with various biological activities. We synthesized Mannich bases of heterocyclic chalcones (9-47) using a one-step Claisen-Schmidt condensation of heterocyclic aldehydes with Mannich bases of acetophenones, and tested the target compounds for cytotoxicity against three human cancer cell lines (prostate, PC-3; breast, MCF-7; nasopharynx, KB) and a multi-drug resistant subline (KB-VIN). Out of the 39 chalcones synthesized, 31 compounds showed potent activity against at least one cell line with IC50 values ranging from 0.03 to 3.80 mu g/mL. Structure-activity relationships (SAR) are also discussed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.018

文献信息

• Nitrogen-containing flavonoid analogues as CDK1/cyclin B inhibitors: Synthesis, SAR analysis, and biological activity
  作者：Shixuan Zhang、Jigang Ma、Yongming Bao、Puwen Yang、Liang Zou、Kangjian Li、Xiaodan Sun

  DOI：10.1016/j.bmc.2008.06.055

  日期：2008.8

  A series of nitrogen-containing flavonoid analogues were designed and synthesized by Mannich reaction, and screened for the inhibitory activities of cyclin-dependent kinases using a FRET-based biochemical assay method. The results showed that C-8 nitrogen-containing baicalein analogues 3a-3f exhibited potent CDK1/Cyclin B inhibitory activities. 5,6,7-Trihydroxy-8-(dimethylaminomethyl)-2-phenyl-4H-chromen-4-one

  通过曼尼希反应设计和合成了一系列含氮类黄酮类似物，并使用基于FRET的生化分析方法筛选了细胞周期蛋白依赖性激酶的抑制活性。结果表明，C-8含氮黄ical素类似物3a-3f表现出有效的CDK1 / Cyclin B抑制活性。5,6,7-三羟基-8-（二甲基氨基甲基）-2-苯基-4H-铬n-4-1 3a，5,6,7-三羟基-8-（吡咯烷基甲基）-2-苯基-4H-铬n- 4-one 3b和5,6,7-三羟基-8-（哌啶基甲基）-2-苯基-4H-chromen-4-one 3c（IC（50）1.05-1.28 microM）的效力是黄ical素2的约六倍（IC（50）6.53 microM）。5,6,7-三羟基-8-（吗啉代甲基）-2-苯基-4H-chromen-4-one 3d，5,6,7-三羟基-8-（硫代吗啉代）-2-苯基-4H-chrom en- 4个3e和5,6，
• Synthesis of Antioxidants for Prevention of Age-Related Macular Degeneration
  作者：Dharati Joshi、James Field、John Murphy、Mohammed Abdelrahim、Heike Schönherr、Janet R. Sparrow、George Ellestad、Koji Nakanishi、Arie Zask

  DOI：10.1021/np300769c

  日期：2013.3.22

  Photooxidation of A2E may be involved in diseases of the macula, and antioxidants could serve as therapeutic agents for these diseases. Inhibitors of A2E photooxidation were prepared by Mannich reaction of the antioxidant quercetin. These compounds contain water-solubilizing amine groups, and several were more potent inhibitors of A2E photooxidation than quercetin.
• Design, synthesis, and biological evaluation of Mannich bases of heterocyclic chalcone analogs as cytotoxic agents
  作者：M. Vijaya Bhaskar Reddy、Chung-Ren Su、Wen-Fei Chiou、Yi-Nan Liu、Rosemary Yin-Hwa Chen、Kenneth F. Bastow、Kuo-Hsiung Lee、Tian-Shung Wu

  DOI：10.1016/j.bmc.2008.06.018

  日期：2008.8

  The chalcone skeleton (1,3-diphenyl-2-propen-1-one) is a unique template that is associated with various biological activities. We synthesized Mannich bases of heterocyclic chalcones (9-47) using a one-step Claisen-Schmidt condensation of heterocyclic aldehydes with Mannich bases of acetophenones, and tested the target compounds for cytotoxicity against three human cancer cell lines (prostate, PC-3; breast, MCF-7; nasopharynx, KB) and a multi-drug resistant subline (KB-VIN). Out of the 39 chalcones synthesized, 31 compounds showed potent activity against at least one cell line with IC50 values ranging from 0.03 to 3.80 mu g/mL. Structure-activity relationships (SAR) are also discussed. (C) 2008 Elsevier Ltd. All rights reserved.