5-(1,1-Dioxothiazinan-2-yl)-7-[5-[(4-fluorophenyl)methyl]-1,2,4-oxadiazol-3-yl]-1,6-naphthyridin-8-ol | 1153774-88-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 5-(1,1-Dioxothiazinan-2-yl)-7-[5-[(4-fluorophenyl)methyl]-1,2,4-oxadiazol-3-yl]-1,6-naphthyridin-8-ol
• 英文别名: 5-(1,1-dioxothiazinan-2-yl)-7-[5-[(4-fluorophenyl)methyl]-1,2,4-oxadiazol-3-yl]-1,6-naphthyridin-8-ol
• CAS: 1153774-88-9
• 化学式: C₂₁H₁₈FN₅O₄S
• 分子量: 455.469
• InChiKey: GHCVXZBYNANXFA-UHFFFAOYSA-N

物化性质

• 沸点：
  784.3±70.0 °C(predicted)
• 密度：
  1.491±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  1,4-丁烷磺内酰胺 、 5-bromo-8-hydroxy-1,6-naphthyridine-7-carbonitrile 、 对氟苯乙酰氯 在 吡啶 、 copper(I) oxide 、 盐酸羟胺 、 potassium carbonate 作用下， 以 乙醇 、 1,4-二氧六环 为溶剂， 生成 5-(1,1-Dioxothiazinan-2-yl)-7-[5-[(4-fluorophenyl)methyl]-1,2,4-oxadiazol-3-yl]-1,6-naphthyridin-8-ol
  参考文献：
  名称：

  The use of oxadiazole and triazole substituted naphthyridines as HIV-1 integrase inhibitors. Part 1: Establishing the pharmacophore

  摘要：

  A series of HIV-1 integrase inhibitors containing a novel metal binding motif consisting of the 8-hydroxy1,6-naphthyridine core and either an oxadiazole or triazole has been identified. The design of the key structural components was based on a two-metal coordination pharmacophore. This report presents initial structure-activity data that shows the new chelation architecture delivers potent inhibition in both enzymatic and antiviral assays. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.090

文献信息

• The use of oxadiazole and triazole substituted naphthyridines as HIV-1 integrase inhibitors. Part 1: Establishing the pharmacophore
  作者：Brian A. Johns、Jason G. Weatherhead、Scott H. Allen、James B. Thompson、Edward P. Garvey、Scott A. Foster、Jerry L. Jeffrey、Wayne H. Miller

  DOI：10.1016/j.bmcl.2009.01.090

  日期：2009.3

  A series of HIV-1 integrase inhibitors containing a novel metal binding motif consisting of the 8-hydroxy1,6-naphthyridine core and either an oxadiazole or triazole has been identified. The design of the key structural components was based on a two-metal coordination pharmacophore. This report presents initial structure-activity data that shows the new chelation architecture delivers potent inhibition in both enzymatic and antiviral assays. (C) 2009 Elsevier Ltd. All rights reserved.