methyl(2-phenylquinazolin-4-yl)amine | 77651-72-0

• 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: methyl(2-phenylquinazolin-4-yl)amine
• 英文别名: N-methyl-2-phenyl-4-quinazolinamine；N-Methyl-2-phenyl-4-chinazolinamin；N-methyl-2-phenylquinazolin-4-amine
• CAS: 77651-72-0
• 化学式: C₁₅H₁₃N₃
• mdl: MFCD17434202
• 分子量: 235.288
• InChiKey: YWMRDABGCCUALK-UHFFFAOYSA-N

物化性质

• 熔点：
  126-127 °C
• 沸点：
  330.3±30.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl(2-phenylquinazolin-4-yl)amine 在 盐酸 作用下， 以 水 、 丙酮 为溶剂， 生成 methyl(2-phenylquinazolin-4-yl)amine hydrochloride
  参考文献：
  名称：

  Design and synthesis of 4-amino-2-phenylquinazolines as novel topoisomerase I inhibitors with molecular modeling

  摘要：

  4-Amino-2-phenylquinazolines 7 were designed as bioisosteres of 3-arylisoquinolinamines 6 that were energy minimized to provide stable conformers. Interestingly, the 2-phenyl ring of 4-amino-2-phenylquinazolines was parallel to the quinazoline ring and improved their DNA intercalation ability in the DNA-topo I complex. Among the synthesized 4-amino group-substituted analogs, 4-cyclohexylamino-2-phenylquinazoline 7h exhibited potent topo I inhibitory activity and strong cytotoxicity. Interestingly, consistency was observed between the cytotoxicities and topo I activities in these quinazoline analogs, suggesting that the target of 4-amino-2-phenylquinazolines is limited to topo I. Molecular docking studies were performed with the Surflex-Dock program to afford the ideal interaction mode of the compound into the binding site of the DNA-topo I complex in order to clarify the topo I activity of 7h. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.012
• 作为产物：
  描述：

  1-methyl-3-[(phenyl)-(phenylimino)methyl]thiourea 在 三聚氯氰 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 2.0h， 生成 methyl(2-phenylquinazolin-4-yl)amine
  参考文献：
  名称：

  Goerdeler, Joachim; Eggers, Wolfgang, Chemische Berichte, 1986, vol. 119, # 12, p. 3737 - 3748

  摘要：

  DOI：

文献信息

• Nielsen, Knud Erik; Pedersen, Erik B., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1980, vol. 34, # 9, p. 637 - 642
  作者：Nielsen, Knud Erik、Pedersen, Erik B.

  DOI：——

  日期：——
• NIELSEN K. E.; PEDERSEN E. B., ACTA CHEM. SCAND., 1980, B 34, NO 9, 637-642
  作者：NIELSEN K. E.、 PEDERSEN E. B.

  DOI：——

  日期：——
• Goerdeler, Joachim; Eggers, Wolfgang, Chemische Berichte, 1986, vol. 119, # 12, p. 3737 - 3748
  作者：Goerdeler, Joachim、Eggers, Wolfgang

  DOI：——

  日期：——
• Design and synthesis of 4-amino-2-phenylquinazolines as novel topoisomerase I inhibitors with molecular modeling
  作者：Thanh Nguyen Le、Su Hui Yang、Daulat Bikram Khadka、Hue Thi My Van、Suk Hee Cho、Youngjoo Kwon、Eung-Seok Lee、Kyung-Tae Lee、Won-Jea Cho

  DOI：10.1016/j.bmc.2011.05.012

  日期：2011.7

  4-Amino-2-phenylquinazolines 7 were designed as bioisosteres of 3-arylisoquinolinamines 6 that were energy minimized to provide stable conformers. Interestingly, the 2-phenyl ring of 4-amino-2-phenylquinazolines was parallel to the quinazoline ring and improved their DNA intercalation ability in the DNA-topo I complex. Among the synthesized 4-amino group-substituted analogs, 4-cyclohexylamino-2-phenylquinazoline 7h exhibited potent topo I inhibitory activity and strong cytotoxicity. Interestingly, consistency was observed between the cytotoxicities and topo I activities in these quinazoline analogs, suggesting that the target of 4-amino-2-phenylquinazolines is limited to topo I. Molecular docking studies were performed with the Surflex-Dock program to afford the ideal interaction mode of the compound into the binding site of the DNA-topo I complex in order to clarify the topo I activity of 7h. (C) 2011 Elsevier Ltd. All rights reserved.