2-bromo-7-(2-carboxyethyl)-8-cyclopropyl-5-oxo-5H-thiazolo[3,2-a]pyridine-3-carboxylic acid methyl ester | 1486364-83-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-bromo-7-(2-carboxyethyl)-8-cyclopropyl-5-oxo-5H-thiazolo[3,2-a]pyridine-3-carboxylic acid methyl ester
• 英文别名: 3-(2-Bromo-8-cyclopropyl-3-methoxycarbonyl-5-oxo-[1,3]thiazolo[3,2-a]pyridin-7-yl)propanoic acid；3-(2-bromo-8-cyclopropyl-3-methoxycarbonyl-5-oxo-[1,3]thiazolo[3,2-a]pyridin-7-yl)propanoic acid
• CAS: 1486364-83-3
• 化学式: C₁₅H₁₄BrNO₅S
• 分子量: 400.25
• InChiKey: FQYJLTUNJJVHOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  2-bromo-7-(2-carboxyethyl)-8-cyclopropyl-5-oxo-5H-thiazolo[3,2-a]pyridine-3-carboxylic acid methyl ester 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 草酰氯 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 2.87h， 生成
  参考文献：
  名称：

  Synthesis of Fluorescent Ring-Fused 2-Pyridone Peptidomimetics

  摘要：

  Thiazolino fused 2-pyridone peptidomimetics are of significant biological importance due to their ability to interfere with adhesive fiber formation in uropathogenic Escherichia coli and oligomerization of amyloid fibers. We have developed an efficient synthetic route to fluorescent BODIPY analogues, with structural diversification from a key intermediate enabling introduction of C-2 substituents and late incorporation of the BODIPY moiety. A mild lithium halide mediated hydrolysis enabled preparation of peptidomimetic fluorophores with useful photophysical properties for further chemical biology applications.

  DOI：

  10.1021/jo401844y
• 作为产物：
  描述：

  7-(2-benzyloxycarbonylethyl)-8-cyclopropyl-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridine-3-carboxylic acid methyl ester 在 1,4-环己二烯 、 10 wt% Pd(OH)2 on carbon 、 sodium hydride 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 16.34h， 生成 2-bromo-7-(2-carboxyethyl)-8-cyclopropyl-5-oxo-5H-thiazolo[3,2-a]pyridine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of Fluorescent Ring-Fused 2-Pyridone Peptidomimetics

  摘要：

  Thiazolino fused 2-pyridone peptidomimetics are of significant biological importance due to their ability to interfere with adhesive fiber formation in uropathogenic Escherichia coli and oligomerization of amyloid fibers. We have developed an efficient synthetic route to fluorescent BODIPY analogues, with structural diversification from a key intermediate enabling introduction of C-2 substituents and late incorporation of the BODIPY moiety. A mild lithium halide mediated hydrolysis enabled preparation of peptidomimetic fluorophores with useful photophysical properties for further chemical biology applications.

  DOI：

  10.1021/jo401844y

文献信息

• Synthesis of Fluorescent Ring-Fused 2-Pyridone Peptidomimetics
  作者：K. Syam Krishnan、Christoffer Bengtsson、James A. D. Good、Shamil Mirkhanov、Erik Chorell、Lennart B.-Å. Johansson、Fredrik Almqvist

  DOI：10.1021/jo401844y

  日期：2013.12.6

  Thiazolino fused 2-pyridone peptidomimetics are of significant biological importance due to their ability to interfere with adhesive fiber formation in uropathogenic Escherichia coli and oligomerization of amyloid fibers. We have developed an efficient synthetic route to fluorescent BODIPY analogues, with structural diversification from a key intermediate enabling introduction of C-2 substituents and late incorporation of the BODIPY moiety. A mild lithium halide mediated hydrolysis enabled preparation of peptidomimetic fluorophores with useful photophysical properties for further chemical biology applications.