(3R)-8-cyclopropyl-7-(naphtalen-1-ylmethyl)-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridine-3,6-dicarboxylic acid 3-methyl ester | 868367-27-5

• 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)-8-cyclopropyl-7-(naphtalen-1-ylmethyl)-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridine-3,6-dicarboxylic acid 3-methyl ester
• 英文别名: (3R)-8-cyclopropyl-3-methoxycarbonyl-7-(naphthalen-1-ylmethyl)-5-oxo-2,3-dihydro-[1,3]thiazolo[3,2-a]pyridine-6-carboxylic acid
• CAS: 868367-27-5
• 化学式: C₂₄H₂₁NO₅S
• 分子量: 435.5
• InChiKey: FZFXSQPZDXBQOO-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R)-8-cyclopropyl-7-(naphtalen-1-ylmethyl)-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridine-3,6-dicarboxylic acid 3-methyl ester 在 lithium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成
  参考文献：
  名称：

  Design, synthesis and evaluation of peptidomimetics based on substituted bicyclic 2-pyridones—Targeting virulence of uropathogenic E. coli

  摘要：

  Substituted bicyclic 2-pyridones, termed pilicides, are dipeptide mimetics that prevent pilus assembly in uropathogenic Escherichia coli. Here, we apply rational design to produce four classes of extended peptidomimetics based on two bioactive 2-pyridones. The key intermediate in the synthesis was an amino-functionalised 2-pyridone scaffold, which could be obtained via a mild and selective nitration and subsequent reduction. Procedures were then developed to further derivatize this amino-substituted core and a total of 24 extended peptidomimetics were synthesised and evaluated for chaperone affinity and in vivo antivirulence activity in P pili producing E coli. Enhanced affinities for the target protein were observed within the generated set of compounds, while the ability to prevent pilus assembly in vivo was significantly decreased compared to the parent lead compounds. The results suggest that the limited in vivo potencies of the analogues are either uptake/distribution related or due to loss in binding specificity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.017
• 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 sodium chlorite 、 sodium dihydrogenphosphate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.0h， 生成 (3R)-8-cyclopropyl-7-(naphtalen-1-ylmethyl)-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridine-3,6-dicarboxylic acid 3-methyl ester
  参考文献：
  名称：

  尿毒症性大肠杆菌中针对菌毛生物发生的双环2-吡啶酮的功能化

  摘要：

  取代的双环2-吡啶酮（称为杀菌剂）可防止尿路致病性大肠杆菌中的菌毛组装。基于具有生物活性的甲基酯保护的2-吡啶酮4，在C-6处的进一步官能化产生了一组新化合物，已对其在尿毒症大肠杆菌中抑制菌毛形成的能力进行了评估。合成中的关键中间体是甲酰化的2-吡啶酮5，可以通过Vilsmeier反应获得。这种多用途的中间体通过还原胺化转化为仲胺和叔胺，也可以通过简单的化学转化将其转化为其他有趣的官能团。

  DOI：

  10.1016/j.tetlet.2007.04.142

文献信息

• Amino methylated 2-pyridinones
  申请人：Hultgren J. Scott

  公开号：US20070082887A1

  公开（公告）日：2007-04-12

  Novel amino methylated 2-pyridinones, precursors, intermediates, and derivatives; the methods for the preparation of the same; uses of the same for inhibiting pili formation in bacteria; and pharmaceutical compositions comprising these compounds are described in this application. The present compounds may be employed to inhibit biofilm formation and thereby inhibit adherence of bacteria to a host cell.

  本申请描述了新型氨基甲基化2-吡啶酮、前体、中间体和衍生物；制备这些化合物的方法；使用这些化合物抑制细菌的菌毛形成；以及包含这些化合物的制药组合物。这些化合物可以用于抑制生物膜的形成，从而抑制细菌附着在宿主细胞上。
• Amino Methylated 2-Pyridinones
  申请人：Hultgren Scott J.

  公开号：US20080311644A1

  公开（公告）日：2008-12-18

  Novel amino methylated 2-pyridinones, precursors, intermediates, and derivatives; the methods for the preparation of the same; uses of the same for inhibiting pili formation in bacteria; and pharmaceutical compositions comprising these compounds are described in this application. The present compounds may be employed to inhibit biofilm formation and thereby inhibit adherence of bacteria to a host cell.

  本申请描述了新型氨基甲基化的2-吡啶酮、前体、中间体和衍生物；其制备方法；以及包含这些化合物的制药组合物的用途，用于抑制细菌的菌毛形成。这些化合物可以用于抑制生物膜的形成，从而抑制细菌对宿主细胞的附着。
• [EN] AMINO METHYLATED 2-PYRIDINONES<br/>[FR] 2-PYRIDINONES AMINO-METHYLES
  申请人：WASHINGTION UNIVERSITY

  公开号：WO2005102330A3

  公开（公告）日：2006-07-13
• US7411066B2
  申请人：——

  公开号：US7411066B2

  公开（公告）日：2008-08-12
• US7915417B2
  申请人：——

  公开号：US7915417B2

  公开（公告）日：2011-03-29