3-(4-bromo-2-fluorophenyl)-9-(4-methoxybenzyl)-2,4,9-triazaspiro[5.5]undec-2-ene | 1403578-86-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-(4-bromo-2-fluorophenyl)-9-(4-methoxybenzyl)-2,4,9-triazaspiro[5.5]undec-2-ene
• 英文别名: 3-(4-bromo-2-fluorophenyl)-9-[(4-methoxyphenyl)methyl]-2,4,9-triazaspiro[5.5]undec-3-ene
• CAS: 1403578-86-8
• 化学式: C₂₂H₂₅BrFN₃O
• 分子量: 446.362
• InChiKey: MUBFMBKAJHNFIF-UHFFFAOYSA-N

物化性质

• 熔点：
  179-181 °C(Solvent: Chloroform ; Hexane)
• 沸点：
  555.0±50.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  36.86
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(4-bromo-2-fluorophenyl)-9-(4-methoxybenzyl)-2,4,9-triazaspiro[5.5]undec-2-ene 在 1-氯乙基氯甲酸酯 、 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.84h， 生成 9-bromo-N-(tert-butyl)-1'-(methanesulfonyl)-2H-spiro[benzo[e]pyrimido[1,2-c][1,3]thiazine-3,4'-piperidin]-6(4H)-imine
  参考文献：
  名称：

  Structure–activity relationship study of pyrimido[1,2-c][1,3]benzothiazin-6-imine derivatives for potent anti-HIV agents

  摘要：

  3,4-Dihydro-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-imine (PD 404182) is an antiretroviral agent with submicromolar inhibitory activity against human immunodeficiency virus-1 (HIV-1) and HIV-2 infection. In the current study, the structure-activity relationships of accessory groups at the 3- and 9-positions of pyrimido[1,2-c][1,3]benzothiazin-6-imine were investigated for the development of more potent anti-HIV agents. Several different derivatives containing a 9-aryl group were designed and synthesized using Suzuki-Miyaura cross-coupling and Ullmann coupling reactions. Modification of the m-methoxyphenyl or benzo[d][1,3]dioxol-5-yl group resulted in improved anti-HIV activity. In addition, the 2,4-diazaspiro[5.5]undec-2-ene-fused benzo[e][1,3]thiazine derivatives were designed and tested for their anti-HIV activities. The most potent 9-(benzo[d][1,3]dioxol-5-yl) derivative was two-threefold more effective against several strains of HIV-1 and HIV-2 than the parent compound, PD 404182. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.030
• 作为产物：
  描述：

  对甲氧基苯甲酰氯 在 lithium aluminium tetrahydride 、 硼烷四氢呋喃络合物 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 3-(4-bromo-2-fluorophenyl)-9-(4-methoxybenzyl)-2,4,9-triazaspiro[5.5]undec-2-ene
  参考文献：
  名称：

  Structure–activity relationship study of pyrimido[1,2-c][1,3]benzothiazin-6-imine derivatives for potent anti-HIV agents

  摘要：

  3,4-Dihydro-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-imine (PD 404182) is an antiretroviral agent with submicromolar inhibitory activity against human immunodeficiency virus-1 (HIV-1) and HIV-2 infection. In the current study, the structure-activity relationships of accessory groups at the 3- and 9-positions of pyrimido[1,2-c][1,3]benzothiazin-6-imine were investigated for the development of more potent anti-HIV agents. Several different derivatives containing a 9-aryl group were designed and synthesized using Suzuki-Miyaura cross-coupling and Ullmann coupling reactions. Modification of the m-methoxyphenyl or benzo[d][1,3]dioxol-5-yl group resulted in improved anti-HIV activity. In addition, the 2,4-diazaspiro[5.5]undec-2-ene-fused benzo[e][1,3]thiazine derivatives were designed and tested for their anti-HIV activities. The most potent 9-(benzo[d][1,3]dioxol-5-yl) derivative was two-threefold more effective against several strains of HIV-1 and HIV-2 than the parent compound, PD 404182. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.030