5,6-dichloro-3,4-dihydro-4-hydroxy-4-trifluoromethylquinazolin-2(1H)-one | 277302-02-0

• 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: 5,6-dichloro-3,4-dihydro-4-hydroxy-4-trifluoromethylquinazolin-2(1H)-one
• 英文别名: 5,6-Dichloro-4-hydroxy-4-(trifluoromethyl)-1,3-dihydroquinazolin-2-one
• CAS: 277302-02-0
• 化学式: C₉H₅Cl₂F₃N₂O₂
• 分子量: 301.052
• InChiKey: MGSYNERDQREDMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  61.4
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,6-dichloro-3,4-dihydro-4-hydroxy-4-trifluoromethylquinazolin-2(1H)-one 在 4 A molecular sieve 作用下， 以 xylene 为溶剂， 以69%的产率得到5,6-dichloro-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
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 5,6-dichloro-3,4-dihydro-4-hydroxy-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