(3R)-6-bromo-7-naphthalen-1-ylmethyl-8-[1-(4-nitro-benzyl)-1H-[1,2,3]triazol-4-yl]-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridine-3-carboxylic acid methyl ester | 1394135-58-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3R)-6-bromo-7-naphthalen-1-ylmethyl-8-[1-(4-nitro-benzyl)-1H-[1,2,3]triazol-4-yl]-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridine-3-carboxylic acid methyl ester
• 英文别名: methyl (3R)-6-bromo-7-(naphthalen-1-ylmethyl)-8-[1-[(4-nitrophenyl)methyl]triazol-4-yl]-5-oxo-2,3-dihydro-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate
• CAS: 1394135-58-0
• 化学式: C₂₉H₂₂BrN₅O₅S
• 分子量: 632.494
• InChiKey: AVRAXETXCQGODX-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  148
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3R)-6-bromo-7-naphthalen-1-ylmethyl-8-[1-(4-nitro-benzyl)-1H-[1,2,3]triazol-4-yl]-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridine-3-carboxylic acid methyl ester 在 palladium 10% on activated carbon 、 甲酸铵 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 21.0h， 生成 (3R)-8-[1-(4-amino-benzyl)-1H-[1,2,3]triazol-4-yl]-7-naphthalen-1-ylmethyl-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridine-3-carboxylic acid
  参考文献：
  名称：

  Design, synthesis and evaluation of triazole functionalized ring-fused 2-pyridones as antibacterial agents

  摘要：

  Antibacterial resistance is today a worldwide problem and the demand for new classes of antibacterial agents with new mode of action is enormous. In the strive for new antibacterial agents that inhibit pilus assembly, an important virulence factor, routes to introduce triazoles in position 8 and 2 of ring-fused bicyclic 2-pyridones have been developed. This was made via Sonogashira couplings followed by Huisgen 1,3-dipolar cycloadditions. The method development made it possible to introduce a diverse series of substituted triazoles and their antibacterial properties were tested in a whole cell pili-dependent biofilm assay. Most of the twenty four candidates tested showed low to no activity but interestingly three compounds, one 8-substituted and two 2-substituted, showed promising activities with EC50's between 9 and 50 mu M. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.018
• 作为产物：
  描述：

  (3R)-6-bromo-8-iodo-7-naphthalen-1-ylmethyl-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridine-3-carboxylic acid methyl ester 在 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium azide 、 potassium carbonate 、 copper(II) sulfate 、 sodium ascorbate 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.25h， 生成 (3R)-6-bromo-7-naphthalen-1-ylmethyl-8-[1-(4-nitro-benzyl)-1H-[1,2,3]triazol-4-yl]-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Design, synthesis and evaluation of triazole functionalized ring-fused 2-pyridones as antibacterial agents

  摘要：

  Antibacterial resistance is today a worldwide problem and the demand for new classes of antibacterial agents with new mode of action is enormous. In the strive for new antibacterial agents that inhibit pilus assembly, an important virulence factor, routes to introduce triazoles in position 8 and 2 of ring-fused bicyclic 2-pyridones have been developed. This was made via Sonogashira couplings followed by Huisgen 1,3-dipolar cycloadditions. The method development made it possible to introduce a diverse series of substituted triazoles and their antibacterial properties were tested in a whole cell pili-dependent biofilm assay. Most of the twenty four candidates tested showed low to no activity but interestingly three compounds, one 8-substituted and two 2-substituted, showed promising activities with EC50's between 9 and 50 mu M. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.018

文献信息

• Design, synthesis and evaluation of triazole functionalized ring-fused 2-pyridones as antibacterial agents
  作者：Christoffer Bengtsson、Anders E.G. Lindgren、Hanna Uvell、Fredrik Almqvist

  DOI：10.1016/j.ejmech.2012.06.018

  日期：2012.8

  Antibacterial resistance is today a worldwide problem and the demand for new classes of antibacterial agents with new mode of action is enormous. In the strive for new antibacterial agents that inhibit pilus assembly, an important virulence factor, routes to introduce triazoles in position 8 and 2 of ring-fused bicyclic 2-pyridones have been developed. This was made via Sonogashira couplings followed by Huisgen 1,3-dipolar cycloadditions. The method development made it possible to introduce a diverse series of substituted triazoles and their antibacterial properties were tested in a whole cell pili-dependent biofilm assay. Most of the twenty four candidates tested showed low to no activity but interestingly three compounds, one 8-substituted and two 2-substituted, showed promising activities with EC50's between 9 and 50 mu M. (C) 2012 Elsevier Masson SAS. All rights reserved.