1'-(aminocarbonyl)-9-bromo-N-(tert-butyl)-2H-spiro[benzo[e]pyrimido[1,2-c][1,3]thiazine-3,4'-piperidin]-6(4H)-imine | 1403578-96-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 1'-(aminocarbonyl)-9-bromo-N-(tert-butyl)-2H-spiro[benzo[e]pyrimido[1,2-c][1,3]thiazine-3,4'-piperidin]-6(4H)-imine
• CAS: 1403578-96-0
• 化学式: C₂₀H₂₆BrN₅OS
• 分子量: 464.429
• InChiKey: CRQCBKXHJBZGGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  28.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  74.29
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1-(4-methoxybenzyl)piperidine-4,4-dicarbonitrile 在 硼烷四氢呋喃络合物 、 1-氯乙基氯甲酸酯 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 9.34h， 生成 1'-(aminocarbonyl)-9-bromo-N-(tert-butyl)-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