3,4-dihydro-4-hydroxy-6-methoxy-4-trifluoromethylquinazolin-2(1H)-one | 214288-02-5

• 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: 3,4-dihydro-4-hydroxy-6-methoxy-4-trifluoromethylquinazolin-2(1H)-one
• 英文别名: 4-Hydroxy-6-methoxy-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one；4-hydroxy-6-methoxy-4-(trifluoromethyl)-1,3-dihydroquinazolin-2-one
• CAS: 214288-02-5
• 化学式: C₁₀H₉F₃N₂O₃
• 分子量: 262.188
• InChiKey: NZMGSTUGNCNCTO-UHFFFAOYSA-N

物化性质

• 熔点：
  195 °C (decomp)
• 沸点：
  357.9±42.0 °C(Predicted)
• 密度：
  1.478±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  70.6
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-4-hydroxy-6-methoxy-4-trifluoromethylquinazolin-2(1H)-one 在 4 A molecular sieve 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 4-(cyclopropylethynyl)-3,4-dihydro-6-methoxy-4-(trifluoromethyl)-2(1H)-quinazolinone
  参考文献：
  名称：

  Inhibition of Clinically Relevant Mutant Variants of HIV-1 by Quinazolinone Non-Nucleoside Reverse Transcriptase Inhibitors

  摘要：

  A series of 4-alkenyl and 4-alkynyl-3,4-dihydro-4-(trifluoromethyl)-2-(1H)-quinazolinones were found to be potent non-nucleoside reverse transcriptase inhibitors (NNRTIs) of human immunodeficiency virus type-1 (HIV-1). The 4-alkenyl-3,4-dihydro-4-(trifluoromethyl) quinazolinones DPC 082 and DPC 083 and the 4-alkynyl-3,4-dihydro-4-(trifluoromethyl) (LK)-quinazolinones DPC 961 and DPC 963 were found to exhibit low nanomolar potency toward wild-type RF virus (IC90 = 2.0, 2.1, 2.0, and 1.3 nM, respectively) and various single and many multiple amino acid substituted HIV-1 mutant viruses.-The increased potency is combined with favorable plasma serum protein binding as demonstrated by improvements in the percent free drug in human plasma when compared to efavirenz: 3.0%, 2.0%, 1.5% 2.8%, and 0.2- 0.5% for DPC 082, DPC 083, DPC 961, DPC 963, and efavirenz, respectively.

  DOI：

  10.1021/jm990580e
• 作为产物：
  描述：

  potassium cyanate 、 1-(2-氨基-5-甲氧基苯基)-2,2,2-三氟乙烷酮 在 溶剂黄146 作用下， 以83%的产率得到3,4-dihydro-4-hydroxy-6-methoxy-4-trifluoromethylquinazolin-2(1H)-one
  参考文献：
  名称：

  Inhibition of Clinically Relevant Mutant Variants of HIV-1 by Quinazolinone Non-Nucleoside Reverse Transcriptase Inhibitors

  摘要：

  A series of 4-alkenyl and 4-alkynyl-3,4-dihydro-4-(trifluoromethyl)-2-(1H)-quinazolinones were found to be potent non-nucleoside reverse transcriptase inhibitors (NNRTIs) of human immunodeficiency virus type-1 (HIV-1). The 4-alkenyl-3,4-dihydro-4-(trifluoromethyl) quinazolinones DPC 082 and DPC 083 and the 4-alkynyl-3,4-dihydro-4-(trifluoromethyl) (LK)-quinazolinones DPC 961 and DPC 963 were found to exhibit low nanomolar potency toward wild-type RF virus (IC90 = 2.0, 2.1, 2.0, and 1.3 nM, respectively) and various single and many multiple amino acid substituted HIV-1 mutant viruses.-The increased potency is combined with favorable plasma serum protein binding as demonstrated by improvements in the percent free drug in human plasma when compared to efavirenz: 3.0%, 2.0%, 1.5% 2.8%, and 0.2- 0.5% for DPC 082, DPC 083, DPC 961, DPC 963, and efavirenz, respectively.

  DOI：

  10.1021/jm990580e