5-chloro-N⁴-(4-chlorophenethyl)-N²-(1-(methylsulfonyl)piperidin-4-yl)pyrimidine-2,4-diamine | 1620988-80-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-chloro-N⁴-(4-chlorophenethyl)-N²-(1-(methylsulfonyl)piperidin-4-yl)pyrimidine-2,4-diamine
• 英文别名: 5-chloro-4-N-[2-(4-chlorophenyl)ethyl]-2-N-(1-methylsulfonylpiperidin-4-yl)pyrimidine-2,4-diamine
• CAS: 1620988-80-8
• 化学式: C₁₈H₂₃Cl₂N₅O₂S
• 分子量: 444.385
• InChiKey: LZLCCSHSRGOIAB-UHFFFAOYSA-N

物化性质

• 熔点：
  171.9-172.5 °C
• 沸点：
  662.240±65.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.430±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  95.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-氯苯乙胺 在 N,N-二异丙基乙胺 作用下， 以 乙二醇甲醚 为溶剂， 反应 12.0h， 生成 5-chloro-N⁴-(4-chlorophenethyl)-N²-(1-(methylsulfonyl)piperidin-4-yl)pyrimidine-2,4-diamine
  参考文献：
  名称：

  One-pot synthesis and antiproliferative activity of novel 2,4-diaminopyrimidine derivatives bearing piperidine and piperazine moieties

  摘要：

  A series of novel 2,4-diaminopyrimidines containing piperidine and piperazine moieties were synthesized via an efficient one-pot methodology. The bioassay tests demonstrated that compounds 27 and 28 displayed much stronger antitumor activities against four human cancer cell lines (HepG2, A549, MDA-MB-231 and MCF-7) than positive control fluorouracil. Particularly, compound 28 showed a two-fold improvement compared to fluorouracil in inhibiting MDA-MB-231 and A549 cell proliferation with IC50 values of 7.46 and 12.78 μM, respectively. Further flow-activated cell sorting analysis revealed that the most promising compound 28 displayed a significant effect on G2/M cell-cycle arrest in a dose-dependent manner in MDA-MB-231 cells.

  DOI：

  10.1016/j.ejmech.2014.07.017

文献信息

• One-pot synthesis and antiproliferative activity of novel 2,4-diaminopyrimidine derivatives bearing piperidine and piperazine moieties
  作者：Wei-Feng Ma、Hai-Kui Yang、Meng-Jin Hu、Qian Li、Tian-Zhu Ma、Zhong-Zhen Zhou、Rui-Yuan Liu、Wen-Wei You、Pei-Liang Zhao

  DOI：10.1016/j.ejmech.2014.07.017

  日期：2014.9

  A series of novel 2,4-diaminopyrimidines containing piperidine and piperazine moieties were synthesized via an efficient one-pot methodology. The bioassay tests demonstrated that compounds 27 and 28 displayed much stronger antitumor activities against four human cancer cell lines (HepG2, A549, MDA-MB-231 and MCF-7) than positive control fluorouracil. Particularly, compound 28 showed a two-fold improvement compared to fluorouracil in inhibiting MDA-MB-231 and A549 cell proliferation with IC50 values of 7.46 and 12.78 μM, respectively. Further flow-activated cell sorting analysis revealed that the most promising compound 28 displayed a significant effect on G2/M cell-cycle arrest in a dose-dependent manner in MDA-MB-231 cells.