3-(3-Amino-4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one | 866261-63-4

• 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: 3-(3-Amino-4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• 英文别名: 3-(3-amino-4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 866261-63-4
• 化学式: C₁₉H₂₁NO₅
• 分子量: 343.379
• InChiKey: PGAJMSRLYVWIPH-UHFFFAOYSA-N

物化性质

• 熔点：
  90-92 °C
• 沸点：
  560.8±50.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(3-Amino-4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 在 4-二甲氨基吡啶 、 lithium hydroxide monohydrate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 O‐(1H‐benzotriazol‐1‐yl)‐N,N,N′,N′‐tetramethyluronium tetrafluoroborate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Pt(IV) complexes conjugating with chalcone analogue as inhibitors of microtubule polymerization exhibited selective inhibition in human cancer cells

  摘要：

  Six novel of Pt(IV) complexes comprising chalcone analogues were synthesized and evaluated for anti proliferative activity using MTF assay. In vitro evaluation revealed that all Pt(IV) complexes showed better and more potent activity against three human cancer cells including CDDP resistant cells than that of their corresponding mother Pt(II) species. Among them, two representative complexes, 14 and 17, exhibited better cell selectivity between cancer cells and normal cells than CDDP. Molecular docking study indicated that complexes 14 and 17 could bind to the colchicine site of tubulin. Moreover, complexes 14 and 17 also remarkably displayed inhibition of cell migration against HUVEC cells in vitro. Molecular mechanism studies suggested that 14 and 17 induced production of reactive oxygen species (ROS), cell cycle arrest at the G2/M phase, and mitochondria-mediated apoptosis by regulating the expression of Bcl-2 family members. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.01.075
• 作为产物：
  描述：

  3',4',5'-三甲氧基苯乙酮 在 铁粉 、 溶剂黄146 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 4.25h， 生成 3-(3-Amino-4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  新的丁二烯衍生物作为微管蛋白聚合抑制剂的合成与评价。

  摘要：

  合成了一系列新的丁二烯衍生物，并被评估为微管蛋白聚合抑制剂，用于治疗癌症。最佳的丁二烯衍生物9a对五种人类癌细胞系的IC50值显示为0.056-0.089μM。本文包括抗增殖活性的机理研究，包括微管蛋白聚合测定，癌细胞形态变化检查，细胞周期停滞分析和凋亡测定。

  DOI：

  10.1016/j.bmc.2017.03.066

文献信息

• The synthesis and evaluation of new butadiene derivatives as tubulin polymerization inhibitors
  作者：Yanqing Pang、Jun Yan、Baijiao An、Ling Huang、Xingshu Li

  DOI：10.1016/j.bmc.2017.03.066

  日期：2017.6

  A series of new butadiene derivatives was synthesized and evaluated as tubulin polymerization inhibitors for the treatment of cancer. The optimal butadiene derivative, 9a, exhibited IC50 values of 0.056-0.089μM for five human cancer cell lines. This paper included a mechanistic study of the antiproliferative activity, including a tubulin polymerization assay, an examination of morphological alterations

  合成了一系列新的丁二烯衍生物，并被评估为微管蛋白聚合抑制剂，用于治疗癌症。最佳的丁二烯衍生物9a对五种人类癌细胞系的IC50值显示为0.056-0.089μM。本文包括抗增殖活性的机理研究，包括微管蛋白聚合测定，癌细胞形态变化检查，细胞周期停滞分析和凋亡测定。
• Synthesis and biological evaluation of a series of tangeretin-derived chalcones
  作者：Jérôme Quintin、Julie Desrivot、Sylviane Thoret、Patrick Le Menez、Thierry Cresteil、Guy Lewin

  DOI：10.1016/j.bmcl.2008.10.126

  日期：2009.1

  A series of chalcones polyoxygenated on the ring A ( with pentamethoxy or 2''-hydroxy-3',4',5',6'-tetramethoxy substitution patterns) was synthesized from tangeretin, a natural Citrus flavonoid. These chalcones were evaluated for their antiproliferative, activation of apoptosis, inhibition of tubulin assembly and antileishmanial activities. Comparison with the reference analogous 3',4',5'-trimethoxylated chalcones showed that such peroxygenated substitution patterns on the ring A were less beneficial to these activities. (C) 2008 Elsevier Ltd. All rights reserved.
• Pt(IV) complexes conjugating with chalcone analogue as inhibitors of microtubule polymerization exhibited selective inhibition in human cancer cells
  作者：Xiaochao Huang、Rizhen Huang、Zhimei Wang、Lingxue Li、Shaohua Gou、Zhixin Liao、Hengshan Wang

  DOI：10.1016/j.ejmech.2018.01.075

  日期：2018.2

  Six novel of Pt(IV) complexes comprising chalcone analogues were synthesized and evaluated for anti proliferative activity using MTF assay. In vitro evaluation revealed that all Pt(IV) complexes showed better and more potent activity against three human cancer cells including CDDP resistant cells than that of their corresponding mother Pt(II) species. Among them, two representative complexes, 14 and 17, exhibited better cell selectivity between cancer cells and normal cells than CDDP. Molecular docking study indicated that complexes 14 and 17 could bind to the colchicine site of tubulin. Moreover, complexes 14 and 17 also remarkably displayed inhibition of cell migration against HUVEC cells in vitro. Molecular mechanism studies suggested that 14 and 17 induced production of reactive oxygen species (ROS), cell cycle arrest at the G2/M phase, and mitochondria-mediated apoptosis by regulating the expression of Bcl-2 family members. (C) 2018 Elsevier Masson SAS. All rights reserved.