(E)-3-(4-methoxy-3-nitrophenyl)-2-methyl-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one | 527750-74-9

• 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)-3-(4-methoxy-3-nitrophenyl)-2-methyl-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• 英文别名: E-3-(3-nitro-4-methoxyphenyl)-2-methyl-1-(3,4,5-trimethoxyphenyl)propenone；(E)-3-(4-Methoxy-3-nitro-phenyl)-2-methyl-1-(3,4,5-trimethoxy-phenyl)-propenone
• CAS: 527750-74-9
• 化学式: C₂₀H₂₁NO₇
• 分子量: 387.389
• InChiKey: PTXFUOFGDDVWNW-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  99.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-methoxy-3-nitrophenyl)-2-methyl-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 在 盐酸 、 铁粉 、 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 生成 E-3-(3-amino-4-methoxyphenyl)-2-methyl-1-(3,4,5-trimethoxyphenyl)propenone
  参考文献：
  名称：

  1,3-Diarylprop-2-en-1-ones, compositions containing them and use thereof

  摘要：

  1,3-二芳基丙烯酮及其衍生物，含有它们的组合物，制备工艺和用途。具有治疗活性的取代1,3-二芳基丙烯酮可用于肿瘤学。

  公开号：

  US20030153611A1
• 作为产物：
  描述：

  1-(3,4,5-trimethoxyphenyl)propan-1-one 、 3-硝基-4-甲氧基苯甲醛 在 哌啶 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以6%的产率得到(E)-3-(4-methoxy-3-nitrophenyl)-2-methyl-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Combretastatin-like chalcones as inhibitors of microtubule polymerization. Part 1: Synthesis and biological evaluation of antivascular activity

  摘要：

  The alpha-methyl chalcone SD400 is a potent inhibitor of tubulin assembly and possesses potent anticancer activity. Various chalcone analogues were synthesized and evaluated for their cell growth inhibitory properties against the K562 human chronic myelogenous leukemia cell line (SD400, IC50 0.21 nM; combretastatin A4 CA4, IC50 2.0 nM). Cell cycle analysis by flow cytometry indicated that these agents are antimitotic (SD400, 83% of the cells are in G(2)/M phase; CA4 90%). They inhibit tubulin assembly at low concentration (SD400, IC50 0.46 mu M; CA4, 0.10 mu M) and compete with [H-3] colchicine for binding to tubulin (8% [H-3] colchicine remained bound to tubulin after competition with SD400 or CA4). Upon treatment with SD400, remarkable cell shape changes were elicited in HUVEC cells, consistent with vasculature damaging activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.039

文献信息

• 1,3-Diarylprop-2-en-1-ones, compositions containing them and use thereof
  申请人：AVENTIS PHARMA S.A.

  公开号：US20030153611A1

  公开（公告）日：2003-08-14

  1,3-Diarylprop-2-en-1-ones and derivatives, compositions containing them, manufacturing process and use. Substituted 1,3-diarylprop-2-en-1-ones with therapeutic activity may be used in oncology.

  1,3-二芳基丙烯酮及其衍生物，含有它们的组合物，制备工艺和用途。具有治疗活性的取代1,3-二芳基丙烯酮可用于肿瘤学。
• Combretastatin-like chalcones as inhibitors of microtubule polymerization. Part 1: Synthesis and biological evaluation of antivascular activity
  作者：Sylvie Ducki、David Rennison、Meiko Woo、Alexander Kendall、Jérémie Fournier Dit Chabert、Alan T. McGown、Nicholas J. Lawrence

  DOI：10.1016/j.bmc.2009.09.039

  日期：2009.11

  The alpha-methyl chalcone SD400 is a potent inhibitor of tubulin assembly and possesses potent anticancer activity. Various chalcone analogues were synthesized and evaluated for their cell growth inhibitory properties against the K562 human chronic myelogenous leukemia cell line (SD400, IC50 0.21 nM; combretastatin A4 CA4, IC50 2.0 nM). Cell cycle analysis by flow cytometry indicated that these agents are antimitotic (SD400, 83% of the cells are in G(2)/M phase; CA4 90%). They inhibit tubulin assembly at low concentration (SD400, IC50 0.46 mu M; CA4, 0.10 mu M) and compete with [H-3] colchicine for binding to tubulin (8% [H-3] colchicine remained bound to tubulin after competition with SD400 or CA4). Upon treatment with SD400, remarkable cell shape changes were elicited in HUVEC cells, consistent with vasculature damaging activity. (C) 2009 Elsevier Ltd. All rights reserved.
• 一种组蛋白去乙酰化酶和微管双靶点抑制剂及其制备方法
  申请人：青岛大学

  公开号：CN109651199B

  公开（公告）日：2022-01-04

  本发明公开了一种组蛋白去乙酰化酶和微管双靶点抑制剂及其制备方法，该抑制剂如I)或II)所示：该抑制剂同时具有微管和组蛋白去乙酰化酶的双重抑制活性。