4-(3-hydroxy-4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)but-3-en-2-one | 1312993-11-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-(3-hydroxy-4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)but-3-en-2-one
• CAS: 1312993-11-5
• 化学式: C₂₀H₂₂O₆
• 分子量: 358.391
• InChiKey: QNSDXHAIVVINGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-(3-hydroxy-4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)but-3-en-2-one 、 溶剂黄146 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  A novel class of trans-methylpyrazoline analogs of combretastatins: Synthesis and in-vitro biological testing

  摘要：

  Thirteen methylpyrazoline analogs (1a-m) of combretastatin A-4 (CA-4, 2) were synthesized. The trans-geometry of the two substituted phenyl moieties was ascertained by a single crystal X-ray diffraction study of compound id. The cytotoxicities of the analogs against the growth of murine B16 melanoma and L1210 lymphoma cells in culture were measured using the MU assay. One of the derivatives, 1j, which has the same substituents as CA-4 was the most active in the series with IC(50) values of 3.3 mu M and 6.8 mu M against the growth of L1210 and B16 cells, respectively. The activity of this analog against human cancer cell lines was confirmed in the NCI 60 panel. The other active analogs against L1210 were 1b and 1f, which gave IC(50) values in the 6-8 mu M range. Compound 1j caused microtubule depolymerization with an EC(50) value of 4.1 mu M. This compound has good water solubility of 372 mu M. Molecular modeling studies using OFT showed that compound 1j adopts a "twisted" conformation mimicking CA-4 that is optimal for binding to the colchicine site of tubulin. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.064
• 作为产物：
  描述：

  异香兰素 、 3,4,5-三甲氧基苯基丙酮 在 哌啶 、 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 4-(3-hydroxy-4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)but-3-en-2-one
  参考文献：
  名称：

  A novel class of trans-methylpyrazoline analogs of combretastatins: Synthesis and in-vitro biological testing

  摘要：

  Thirteen methylpyrazoline analogs (1a-m) of combretastatin A-4 (CA-4, 2) were synthesized. The trans-geometry of the two substituted phenyl moieties was ascertained by a single crystal X-ray diffraction study of compound id. The cytotoxicities of the analogs against the growth of murine B16 melanoma and L1210 lymphoma cells in culture were measured using the MU assay. One of the derivatives, 1j, which has the same substituents as CA-4 was the most active in the series with IC(50) values of 3.3 mu M and 6.8 mu M against the growth of L1210 and B16 cells, respectively. The activity of this analog against human cancer cell lines was confirmed in the NCI 60 panel. The other active analogs against L1210 were 1b and 1f, which gave IC(50) values in the 6-8 mu M range. Compound 1j caused microtubule depolymerization with an EC(50) value of 4.1 mu M. This compound has good water solubility of 372 mu M. Molecular modeling studies using OFT showed that compound 1j adopts a "twisted" conformation mimicking CA-4 that is optimal for binding to the colchicine site of tubulin. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.064

文献信息

• A novel class of trans-methylpyrazoline analogs of combretastatins: Synthesis and in-vitro biological testing
  作者：Megan Lee、Olivia Brockway、Armaan Dandavati、Samuel Tzou、Robert Sjoholm、Vijay Satam、Cara Westbrook、Susan L. Mooberry、Matthias Zeller、Balaji Babu、Moses Lee

  DOI：10.1016/j.ejmech.2011.03.064

  日期：2011.7

  Thirteen methylpyrazoline analogs (1a-m) of combretastatin A-4 (CA-4, 2) were synthesized. The trans-geometry of the two substituted phenyl moieties was ascertained by a single crystal X-ray diffraction study of compound id. The cytotoxicities of the analogs against the growth of murine B16 melanoma and L1210 lymphoma cells in culture were measured using the MU assay. One of the derivatives, 1j, which has the same substituents as CA-4 was the most active in the series with IC(50) values of 3.3 mu M and 6.8 mu M against the growth of L1210 and B16 cells, respectively. The activity of this analog against human cancer cell lines was confirmed in the NCI 60 panel. The other active analogs against L1210 were 1b and 1f, which gave IC(50) values in the 6-8 mu M range. Compound 1j caused microtubule depolymerization with an EC(50) value of 4.1 mu M. This compound has good water solubility of 372 mu M. Molecular modeling studies using OFT showed that compound 1j adopts a "twisted" conformation mimicking CA-4 that is optimal for binding to the colchicine site of tubulin. (C) 2011 Elsevier Masson SAS. All rights reserved.