3-(4-bromo-2-fluorophenyl)-9-oxa-2,4-diazaspiro[5.5]undec-2-ene | 1403578-85-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-bromo-2-fluorophenyl)-9-oxa-2,4-diazaspiro[5.5]undec-2-ene
• 英文别名: 3-(4-bromo-2-fluorophenyl)-9-oxa-2,4-diazaspiro[5.5]undec-3-ene
• CAS: 1403578-85-7
• 化学式: C₁₄H₁₆BrFN₂O
• 分子量: 327.196
• InChiKey: SOOJHMUOGSHKNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  33.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  叔丁基异硫氰酸酯 、 3-(4-bromo-2-fluorophenyl)-9-oxa-2,4-diazaspiro[5.5]undec-2-ene 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 以78%的产率得到9-bromo-N-(tert-butyl)-2',3',5',6'-tetrahydro-2H-spiro[benzo[e]pyrimido[1,2-c][1,3]thiazine-3,4'-pyran]-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：

  四氢吡喃-4,4-二甲腈 、 4-溴-2-氟苯甲醛 在 硼烷四氢呋喃络合物 、 碘 、 potassium carbonate 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 8.5h， 以11%的产率得到3-(4-bromo-2-fluorophenyl)-9-oxa-2,4-diazaspiro[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