2,4-bis(pivaloylamino)-6-methylquinazoline | 1369932-36-4

• 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: 2,4-bis(pivaloylamino)-6-methylquinazoline
• 英文别名: N-[2-(2,2-dimethylpropanoylamino)-6-methylquinazolin-4-yl]-2,2-dimethylpropanamide
• CAS: 1369932-36-4
• 化学式: C₁₉H₂₆N₄O₂
• 分子量: 342.441
• InChiKey: UQOQFZPPNVVSAD-UHFFFAOYSA-N

物化性质

• 熔点：
  192.7-193.8 °C
• 密度：
  1.174±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  84
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-bis(pivaloylamino)-6-methylquinazoline 在 盐酸 、 potassium phosphate 、 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 (2,4-diaminoquinazolin-6-yl)methyl 4-(4-fluorophenyl)piperazine-1-carbodithioate
  参考文献：
  名称：

  Synthesis and antiproliferative activity of 4-substituted-piperazine-1-carbodithioate derivatives of 2,4-diaminoquinazoline

  摘要：

  A novel series of 4-substituted-piperazine-1-carbodithioate derivatives of 2,4-diaminoquinazoline were synthesized and tested for their antiproliferative activities against five human cancer cell lines including A549 (lung cancer), MCF-7 (breast adenocarcinoma), HeLa (cervical carcinoma), HT29 and HCT-116 (colorectal cancer). Most of the synthesized compounds showed broad spectrum antiproliferative activity (IC50 1.47-11.83 mu M), of which 8f, 8m and 8q were the most active members with IC50 values in the range of 1.58-2.27, 1.84-3.27 and 1.47-4.68 mu M against five cancer cell lines examined, respectively. Further investigations revealed that compounds 8f, 8m and 8q exhibited weak inhibition against dihydrofolate reductase and no activity against thymidylate synthase, while induced DNA damage and activated the G2/M checkpoint in HCT-116 cells. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.017
• 作为产物：
  描述：

  2-氨基-5-甲基苯腈 在 盐酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 生成 2,4-bis(pivaloylamino)-6-methylquinazoline
  参考文献：
  名称：

  Synthesis and antiproliferative activity of 4-substituted-piperazine-1-carbodithioate derivatives of 2,4-diaminoquinazoline

  摘要：

  A novel series of 4-substituted-piperazine-1-carbodithioate derivatives of 2,4-diaminoquinazoline were synthesized and tested for their antiproliferative activities against five human cancer cell lines including A549 (lung cancer), MCF-7 (breast adenocarcinoma), HeLa (cervical carcinoma), HT29 and HCT-116 (colorectal cancer). Most of the synthesized compounds showed broad spectrum antiproliferative activity (IC50 1.47-11.83 mu M), of which 8f, 8m and 8q were the most active members with IC50 values in the range of 1.58-2.27, 1.84-3.27 and 1.47-4.68 mu M against five cancer cell lines examined, respectively. Further investigations revealed that compounds 8f, 8m and 8q exhibited weak inhibition against dihydrofolate reductase and no activity against thymidylate synthase, while induced DNA damage and activated the G2/M checkpoint in HCT-116 cells. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.017

文献信息

• Synthesis and antiproliferative activity of 4-substituted-piperazine-1-carbodithioate derivatives of 2,4-diaminoquinazoline
  作者：Sheng-Li Cao、Ying Han、Chong-Zhen Yuan、Yao Wang、Zhi-Kai Xiahou、Ji Liao、Rui-Ting Gao、Bei-Bei Mao、Bao-Li Zhao、Zhong-Feng Li、Xingzhi Xu

  DOI：10.1016/j.ejmech.2013.04.017

  日期：2013.6

  A novel series of 4-substituted-piperazine-1-carbodithioate derivatives of 2,4-diaminoquinazoline were synthesized and tested for their antiproliferative activities against five human cancer cell lines including A549 (lung cancer), MCF-7 (breast adenocarcinoma), HeLa (cervical carcinoma), HT29 and HCT-116 (colorectal cancer). Most of the synthesized compounds showed broad spectrum antiproliferative activity (IC50 1.47-11.83 mu M), of which 8f, 8m and 8q were the most active members with IC50 values in the range of 1.58-2.27, 1.84-3.27 and 1.47-4.68 mu M against five cancer cell lines examined, respectively. Further investigations revealed that compounds 8f, 8m and 8q exhibited weak inhibition against dihydrofolate reductase and no activity against thymidylate synthase, while induced DNA damage and activated the G2/M checkpoint in HCT-116 cells. (C) 2013 Elsevier Masson SAS. All rights reserved.