4-(4-chlorophenyl)-6-(3,4,5-trimethoxyphenyl)-3,4-dihydropyrimidine-2(1H)-thione | 1073793-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-chlorophenyl)-6-(3,4,5-trimethoxyphenyl)-3,4-dihydropyrimidine-2(1H)-thione
• 英文别名: 4-(4-chlorophenyl)-6-(3,4,5-trimethoxyphenyl)-3,4-dihydro-1H-pyrimidine-2-thione
• CAS: 1073793-06-2
• 化学式: C₁₉H₁₉ClN₂O₃S
• 分子量: 390.89
• InChiKey: FEWGHHLJHDOSMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-3-(4-chlorophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 、 硫脲 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以50%的产率得到4-(4-chlorophenyl)-6-(3,4,5-trimethoxyphenyl)-3,4-dihydropyrimidine-2(1H)-thione
  参考文献：
  名称：

  某些新型查尔酮类似化合物的设计，合成和细胞毒活性

  摘要：

  设计并合成了一系列查尔酮类似化合物。用刚性杂环部分或取代的芳族胺取代/取代母体查尔酮的烯酮或烯键，得到十九种目标化合物。筛选了针对乳腺癌和肝癌细胞以及乳腺癌和肝正常细胞的细胞毒性活性。还评估了目标化合物对微管蛋白β聚合的抑制活性。目标化合物2e，3a，3b，3c，4a-4d，5a，5b和6显示出对MCF-7和HepG2均具有广谱优异的抗癌活性。化合物4a显示出最大的TUBb抑制活性。

  DOI：

  10.1016/j.ejmech.2016.09.099

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.
• Design, synthesis and cytotoxic activity of certain novel chalcone analogous compounds
  作者：S. El-Meligie、Azza T. Taher、Aliaa M. Kamal、A. Youssef

  DOI：10.1016/j.ejmech.2016.09.099

  日期：2017.1

  of chalcone analogous compounds were designed and synthesized. Replacing/substituting the enone or ethylenic bridge of the parent chalcone with rigid heterocyclic moieties or substituted aromatic amines gave nineteen target compounds. Their cytotoxic activities were screened against both breast and liver cancer cells as well as breast and liver normal cells. Target compounds were also evaluated for

  设计并合成了一系列查尔酮类似化合物。用刚性杂环部分或取代的芳族胺取代/取代母体查尔酮的烯酮或烯键，得到十九种目标化合物。筛选了针对乳腺癌和肝癌细胞以及乳腺癌和肝正常细胞的细胞毒性活性。还评估了目标化合物对微管蛋白β聚合的抑制活性。目标化合物2e，3a，3b，3c，4a-4d，5a，5b和6显示出对MCF-7和HepG2均具有广谱优异的抗癌活性。化合物4a显示出最大的TUBb抑制活性。