N-(tert-butyl)-3,4-dihydro-9-(naphthalene-2-yl)-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-imine | 1410124-48-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(tert-butyl)-3,4-dihydro-9-(naphthalene-2-yl)-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-imine
• 英文别名: N-tert-butyl-9-naphthalen-2-yl-3,4-dihydro-2H-pyrimido[1,2-c][1,3]benzothiazin-6-imine
• CAS: 1410124-48-9
• 化学式: C₂₅H₂₅N₃S
• 分子量: 399.56
• InChiKey: QFRGGMBRIBLHKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(tert-butyl)-3,4-dihydro-9-(naphthalene-2-yl)-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-imine 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以73%的产率得到3,4-dihydro-9-(naphthalene-2-yl)-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-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：

  9-bromo-N-(tert-butyl)-3,4-dihydro-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-imine 、 2-萘硼酸 在 四(三苯基膦)钯 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 1.0h， 以94%的产率得到N-(tert-butyl)-3,4-dihydro-9-(naphthalene-2-yl)-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-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