1-(2,4-Dimethoxy-benzyl)-6-fluoro-3-phenylaminomethyl-7-pyrrolidin-1-yl-1H-[1,8]naphthyridin-4-one | 779343-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-(2,4-Dimethoxy-benzyl)-6-fluoro-3-phenylaminomethyl-7-pyrrolidin-1-yl-1H-[1,8]naphthyridin-4-one
• CAS: 779343-22-5
• 化学式: C₂₈H₂₉FN₄O₃
• 分子量: 488.562
• InChiKey: HHZOHXJHMCKRSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  68.62
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-(2,4-Dimethoxy-benzyl)-6-fluoro-3-phenylaminomethyl-7-pyrrolidin-1-yl-1H-[1,8]naphthyridin-4-one 在 三氟乙酸 作用下， 生成 6-Fluoro-3-phenylaminomethyl-7-pyrrolidin-1-yl-1H-[1,8]naphthyridin-4-one
  参考文献：
  名称：

  Novel inhibitors of bacterial protein synthesis: structure–activity relationships for 1,8-naphthyridine derivatives incorporating position 3 and 4 variants

  摘要：

  Structure-activity relationships for a recently discovered novel ribosome inhibitor (NRI) class of antibacterials were investigated. Preliminary efforts to optimize protein synthesis inhibitory activity of the series through modification of positions 3 and 4 of the naphthyridone lead template resulted in the identification of several biochemically potent analogues. A lack of corresponding whole cell antibacterial activity is thought to be a consequence of poor cellular penetration as evidenced by the enhancement of activity observed for a lead analogue tested in the presence of a cell permeabilizing agent. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.091
• 作为产物：
  描述：

  1-(2,4-dimethoxybenzyl)-6-fluoro-4-oxo-7-(pyrrolidin-1-yl)-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid ethyl ester 在 lithium hydroxide 、 二异丁基氢化铝 、 sodium cyanoborohydride 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 生成 1-(2,4-Dimethoxy-benzyl)-6-fluoro-3-phenylaminomethyl-7-pyrrolidin-1-yl-1H-[1,8]naphthyridin-4-one
  参考文献：
  名称：

  Novel inhibitors of bacterial protein synthesis: structure–activity relationships for 1,8-naphthyridine derivatives incorporating position 3 and 4 variants

  摘要：

  Structure-activity relationships for a recently discovered novel ribosome inhibitor (NRI) class of antibacterials were investigated. Preliminary efforts to optimize protein synthesis inhibitory activity of the series through modification of positions 3 and 4 of the naphthyridone lead template resulted in the identification of several biochemically potent analogues. A lack of corresponding whole cell antibacterial activity is thought to be a consequence of poor cellular penetration as evidenced by the enhancement of activity observed for a lead analogue tested in the presence of a cell permeabilizing agent. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.091