4-ethyl-3-methyl-1-oxo-10,11-dihydro-2H-pyrido[4,3-b]benzo[f][1,4]thiazepin-10-yl carbonitrile

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-ethyl-3-methyl-1-oxo-10,11-dihydro-2H-pyrido[4,3-b]benzo[f][1,4]thiazepin-10-yl carbonitrile
• 英文别名: 1-ethyl-2-methyl-4-oxo-5,6-dihydro-3H-pyrido[4,3-b][1,4]benzothiazepine-6-carbonitrile
• 化学式: C₁₆H₁₅N₃OS
• 分子量: 297.381
• InChiKey: AXVSBEHFDCOQCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  94.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-ethyl-4-hydroxy-6-methyl-3-nitro-2(1H)-pyridinone 在 palladium on activated charcoal 四丁基氟化铵 、 氢气 、 碳酸氢钠 、 potassium carbonate 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 sodium thiosulfate 、 N,N-二异丙基乙胺 、 zinc dibromide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 20.0~50.0 ℃ 、101.33 kPa 条件下， 反应 32.86h， 生成 4-ethyl-3-methyl-1-oxo-10,11-dihydro-2H-pyrido[4,3-b]benzo[f][1,4]thiazepin-10-yl carbonitrile
  参考文献：
  名称：

  Tosylation/mesylation of 4-hydroxy-3-nitro-2-pyridinones as an activation step in the construction of dihydropyrido[3,4-b] benzo[f][1,4]thiazepin-1-one based anti-HIV agents

  摘要：

  Reaction of 4-hydroxy-3-nitropyridinone 8 with TsCl and MsCl, respectively, resulted in rapid and quantitative formation of ditosylate 13 and dimesylate 16. Through chemoselective reaction of 16 with thiophenol 17 the key 4-thioaryl substituted intermediate 18 was obtained in 78% yield. This compound was efficiently converted to the target tricyclic products 4a and b. Compound 4a, in particular, is a potent inhibitor in vitro (IC50 = 2 nM) of wild type HIV-1 replication. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.128

文献信息

• Tosylation/mesylation of 4-hydroxy-3-nitro-2-pyridinones as an activation step in the construction of dihydropyrido[3,4-b] benzo[f][1,4]thiazepin-1-one based anti-HIV agents
  作者：Pierre Storck、Anne-Marie Aubertin、David S. Grierson

  DOI：10.1016/j.tetlet.2005.02.128

  日期：2005.4

  Reaction of 4-hydroxy-3-nitropyridinone 8 with TsCl and MsCl, respectively, resulted in rapid and quantitative formation of ditosylate 13 and dimesylate 16. Through chemoselective reaction of 16 with thiophenol 17 the key 4-thioaryl substituted intermediate 18 was obtained in 78% yield. This compound was efficiently converted to the target tricyclic products 4a and b. Compound 4a, in particular, is a potent inhibitor in vitro (IC50 = 2 nM) of wild type HIV-1 replication. (c) 2005 Elsevier Ltd. All rights reserved.