4,6-bis(3,4,5-trimethoxyphenyl)-3,4-dihydro-1H-pyrimidine-2-thione | 1073792-91-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4,6-bis(3,4,5-trimethoxyphenyl)-3,4-dihydro-1H-pyrimidine-2-thione
• CAS: 1073792-91-2
• 化学式: C₂₂H₂₆N₂O₆S
• 分子量: 446.524
• InChiKey: LGGZBFJYIWUWIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2E)-1-(3',4',5'-trimethoxyphenyl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one 、 硫脲 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 4,6-bis(3,4,5-trimethoxyphenyl)-3,4-dihydro-1H-pyrimidine-2-thione
  参考文献：
  名称：

  1,2,3,4-Tetrahydro-2-thioxopyrimidine analogs of combretastatin-A4

  摘要：

  Eleven 1,2,3,4-tetrahydro-2-thioxopyrimidine analogs of combretastatin-A4 (CA-4) were synthesized and their cytotoxicity against the growth of two murine cancer cell lines (B16 melanoma and L1210 leukemia) in culture was determined using an MTT assay. Two 2-thioxopyrimidine analogs 8f and 9a exhibited significant activity IC50 <1 mu M for L1210 and <10 mu M for B16 cells). Exposure of A-10 cells to 8f and 9a produced a significant reduction in cellular microtubules in interphase cells, with an EC50 value of 4.4 and 2.9 mu M, respectively, for microtubule loss. Molecular modeling studies using MacSpartan indicated that the two active 2-thioxopyrimidine analogs preferably adopt a twisted conformation, similar to CA-4, affirming that conformation and structure are connected to activity. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.11.030

文献信息

• 1,2,3,4-Tetrahydro-2-thioxopyrimidine analogs of combretastatin-A4
  作者：Lauren Lee、Ryan Davis、Jenna Vanderham、Patrice Hills、Hilary Mackay、Toni Brown、Susan L. Mooberry、Moses Lee

  DOI：10.1016/j.ejmech.2007.11.030

  日期：2008.9

  Eleven 1,2,3,4-tetrahydro-2-thioxopyrimidine analogs of combretastatin-A4 (CA-4) were synthesized and their cytotoxicity against the growth of two murine cancer cell lines (B16 melanoma and L1210 leukemia) in culture was determined using an MTT assay. Two 2-thioxopyrimidine analogs 8f and 9a exhibited significant activity IC50 <1 mu M for L1210 and <10 mu M for B16 cells). Exposure of A-10 cells to 8f and 9a produced a significant reduction in cellular microtubules in interphase cells, with an EC50 value of 4.4 and 2.9 mu M, respectively, for microtubule loss. Molecular modeling studies using MacSpartan indicated that the two active 2-thioxopyrimidine analogs preferably adopt a twisted conformation, similar to CA-4, affirming that conformation and structure are connected to activity. (C) 2007 Elsevier Masson SAS. All rights reserved.