hexyl N-((2-methyl-4(3H)-quinazolinon-6-yl)methyl)dithiocarbamate | 1235851-26-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: hexyl N-((2-methyl-4(3H)-quinazolinon-6-yl)methyl)dithiocarbamate
• 英文别名: hexyl N-[(2-methyl-4-oxo-3H-quinazolin-6-yl)methyl]carbamodithioate
• CAS: 1235851-26-9
• 化学式: C₁₇H₂₃N₃OS₂
• 分子量: 349.521
• InChiKey: UFFCIRPWUBASDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二硫化碳 、 溴己烷 、 6-(aminomethyl)-2-methyl-4(3H)-quinazolinone dihydrochloride 在 potassium phosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以67%的产率得到hexyl N-((2-methyl-4(3H)-quinazolinon-6-yl)methyl)dithiocarbamate
  参考文献：
  名称：

  Synthesis and cytotoxic activity of N-((2-methyl-4(3H)-quinazolinon-6-yl)methyl)dithiocarbamates

  摘要：

  A series of N4(2-methyl-4(3H)-quinazolinon-6-yl)methyl)dithiocarbamates 5a-w were synthesized and evaluated for their cytotoxic activity against five human cancer cell lines. We found that compound 5k inhibited proliferation of A549, MCF-7, HeLa, HT29 and HCT-116 cells with IC(50) values of 5.44, 7.15, 12.16, 10.35 and 11.44 mu M, respectively. Compound 5i was the most potent with an IC(50) value of 3.65 mu M against proliferation of MCF-7 cells, while 5n was the most potent with an IC(50) value of 5.09 mu M against proliferation of A549 cells. Cell cycle analysis showed that both 51 and 5k arrested A549 cells at S and G2/M phases, suggesting that these compounds act through mechanisms different from 5-Fluorouracil, which arrests cells at S phase only. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.038

文献信息

• Synthesis and cytotoxic activity of N-((2-methyl-4(3H)-quinazolinon-6-yl)methyl)dithiocarbamates
  作者：Sheng-Li Cao、Yao Wang、Lin Zhu、Ji Liao、Yan-Wen Guo、Lin-Lin Chen、Hong-Qin Liu、Xingzhi Xu

  DOI：10.1016/j.ejmech.2010.05.038

  日期：2010.9

  A series of N4(2-methyl-4(3H)-quinazolinon-6-yl)methyl)dithiocarbamates 5a-w were synthesized and evaluated for their cytotoxic activity against five human cancer cell lines. We found that compound 5k inhibited proliferation of A549, MCF-7, HeLa, HT29 and HCT-116 cells with IC(50) values of 5.44, 7.15, 12.16, 10.35 and 11.44 mu M, respectively. Compound 5i was the most potent with an IC(50) value of 3.65 mu M against proliferation of MCF-7 cells, while 5n was the most potent with an IC(50) value of 5.09 mu M against proliferation of A549 cells. Cell cycle analysis showed that both 51 and 5k arrested A549 cells at S and G2/M phases, suggesting that these compounds act through mechanisms different from 5-Fluorouracil, which arrests cells at S phase only. (C) 2010 Elsevier Masson SAS. All rights reserved.