ethyl 4-(benzo[d][1,3]dioxol-5-yl)-2-thioxo-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 716365-95-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: ethyl 4-(benzo[d][1,3]dioxol-5-yl)-2-thioxo-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: ethyl 4-(1,3-benzodioxol-5-yl)-2-sulfanylidene-6-(trifluoromethyl)-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 716365-95-6
• 化学式: C₁₅H₁₃F₃N₂O₄S
• 分子量: 374.34
• InChiKey: DLCKIIZLTMMIAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 4-(benzo[d][1,3]dioxol-5-yl)-2-thioxo-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate 、 2-溴-4'-(三氟甲基)苯乙酮 在 吡啶 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以86%的产率得到ethyl 4-(benzo[d][1,3]dioxol-5-yl)-2-(2-oxo-2-(4-(trifluoromethyl)phenyl)ethylthio)-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Synthesis and in vitro cytotoxicity evaluation of some fluorinated hexahydropyrimidine derivatives

  摘要：

  A series of trifluoromethylated hexahydropyrimidine and tetrahydropyrimidine derivatives were synthesized and their in vitro cytotoxic activities were determined in colon cancer cell line (COLO 320 HSR). Compounds 4f, 4g, 4k, 5, and 7 proved to be the most active in this series of compounds. They represent promising new leads for the development of highly potent and selective anticancer compounds. All the compounds are lipophilic due to the trifluoromethyl group, and are thus expected to penetrate the membrane in appreciable concentration. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.022
• 作为产物：
  描述：

  ethyl (4R,5S,6R)-6-(1,3-benzodioxol-5-yl)-4-hydroxy-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinane-5-carboxylate 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以56%的产率得到ethyl 4-(benzo[d][1,3]dioxol-5-yl)-2-thioxo-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Synthesis and in vitro cytotoxicity evaluation of some fluorinated hexahydropyrimidine derivatives

  摘要：

  A series of trifluoromethylated hexahydropyrimidine and tetrahydropyrimidine derivatives were synthesized and their in vitro cytotoxic activities were determined in colon cancer cell line (COLO 320 HSR). Compounds 4f, 4g, 4k, 5, and 7 proved to be the most active in this series of compounds. They represent promising new leads for the development of highly potent and selective anticancer compounds. All the compounds are lipophilic due to the trifluoromethyl group, and are thus expected to penetrate the membrane in appreciable concentration. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.022

文献信息

• Synthesis and in vitro cytotoxicity evaluation of some fluorinated hexahydropyrimidine derivatives
  作者：Oluropo C. Agbaje、Olugbeminiyi O. Fadeyi、S. Adamson Fadeyi、Lewis. E. Myles、Cosmas O. Okoro

  DOI：10.1016/j.bmcl.2010.12.022

  日期：2011.2

  A series of trifluoromethylated hexahydropyrimidine and tetrahydropyrimidine derivatives were synthesized and their in vitro cytotoxic activities were determined in colon cancer cell line (COLO 320 HSR). Compounds 4f, 4g, 4k, 5, and 7 proved to be the most active in this series of compounds. They represent promising new leads for the development of highly potent and selective anticancer compounds. All the compounds are lipophilic due to the trifluoromethyl group, and are thus expected to penetrate the membrane in appreciable concentration. (C) 2010 Elsevier Ltd. All rights reserved.