2-(trimethylsilyl)ethyl 8-cyclopropyl-2-ethynyl-7-(naphthalen-1-ylmethyl)-5-oxo-5H-thiazolo[3,2-a]pyridine-3-carboxylate | 1345974-41-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(trimethylsilyl)ethyl 8-cyclopropyl-2-ethynyl-7-(naphthalen-1-ylmethyl)-5-oxo-5H-thiazolo[3,2-a]pyridine-3-carboxylate
• 英文别名: 2-Trimethylsilylethyl 8-cyclopropyl-2-ethynyl-7-(naphthalen-1-ylmethyl)-5-oxo-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate
• CAS: 1345974-41-5
• 化学式: C₂₉H₂₉NO₃SSi
• 分子量: 499.706
• InChiKey: HDJDQXYWHCMHFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.46
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 8-cyclopropyl-2-ethynyl-7-(naphthalen-1-ylmethyl)-5-oxo-5H-thiazolo[3,2-a]pyridine-3-carboxylate 在 1,3-双(二苯基膦)丙烷 、 palladium diacetate 作用下， 以 二氯甲烷 、 三氟乙酸 为溶剂， 反应 1.0h， 以88%的产率得到5-cyclopropyl-3-methylidene-6-(naphthalen-1-ylmethyl)-8H-furo[3',4':4,5][1,3]thiazolo[3,2-a]pyridine-1,8(3H)-dione
  参考文献：
  名称：

  A Selective Intramolecular 5-exo-dig or 6-endo-dig Cyclization en Route to 2-Furanone or 2-Pyrone Containing Tricyclic Scaffolds

  摘要：

  Ringfused bicyclic 2-pyridones exhibit interesting biological properties against pili assembly in uropathogenic Escherichia coli (Pinkner, J. S. et al. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 17897-17902; Aberg, V. et al. Org. Biomol. Chem. 2007, 5, 1827-1834) as well as curli formation (Cegelski, L. et al. Nat. Chem. Biol. 2009, 5, 913-919). In the search for new ring-fused central fragments, highly selective synthetic routes to the 2-furanone or 2-pyrone containing tricyclic scaffolds 1 and 2 have been developed.

  DOI：

  10.1021/jo201952p
• 作为产物：
  描述：

  methyl (3R)-8-cyclopropyl-7-(naphthalen-1-ylmethyl)-5-oxo-2,3-dihydro-5H-[1,3 ]thiazolo[3,2-a]pyridine-3-carboxylate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 草酰氯 、 三氯溴甲烷 、 sodium hydride 、 potassium carbonate 、 三乙胺 、 N,N-二甲基甲酰胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 2-(三甲硅基)乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 9.17h， 生成 2-(trimethylsilyl)ethyl 8-cyclopropyl-2-ethynyl-7-(naphthalen-1-ylmethyl)-5-oxo-5H-thiazolo[3,2-a]pyridine-3-carboxylate
  参考文献：
  名称：

  A Selective Intramolecular 5-exo-dig or 6-endo-dig Cyclization en Route to 2-Furanone or 2-Pyrone Containing Tricyclic Scaffolds

  摘要：

  Ringfused bicyclic 2-pyridones exhibit interesting biological properties against pili assembly in uropathogenic Escherichia coli (Pinkner, J. S. et al. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 17897-17902; Aberg, V. et al. Org. Biomol. Chem. 2007, 5, 1827-1834) as well as curli formation (Cegelski, L. et al. Nat. Chem. Biol. 2009, 5, 913-919). In the search for new ring-fused central fragments, highly selective synthetic routes to the 2-furanone or 2-pyrone containing tricyclic scaffolds 1 and 2 have been developed.

  DOI：

  10.1021/jo201952p

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.