1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid 3-butene ester | 1430212-98-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid 3-butene ester
• 英文别名: But-3-enyl 1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate；but-3-enyl 1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate
• CAS: 1430212-98-8
• 化学式: C₁₆H₁₈N₂O₃
• 分子量: 286.331
• InChiKey: MHUFRPXWGWEEIX-UHFFFAOYSA-N

物化性质

• 沸点：
  437.2±45.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  59.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid 3-butene ester 以 aq. buffer 为溶剂， 生成 萘啶酸
  参考文献：
  名称：

  Synthesis and release kinetics of polymerisable ester drug conjugates: towards pH-responsive infection-resistant urinary biomaterials

  摘要：

  Herein we report the synthesis, characterisation and hydrolytic release kinetics of a suite of novel, polymerisable ester quinolone conjugates with varying alkenyl chain lengths. Hydrolysis was shown to proceed up to 17-fold faster upon elevation of pH from neutral to pH 9.29, making these conjugates attractive for the development of 'designer' infection-resistant urinary biomaterials exploiting the increase in urine pH reported at the onset of catheter-associated infection to trigger drug release. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.020
• 作为产物：
  描述：

  3-丁烯-1-醇 、 nalidixic acid 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.42h， 以62%的产率得到1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid 3-butene ester
  参考文献：
  名称：

  Synthesis and release kinetics of polymerisable ester drug conjugates: towards pH-responsive infection-resistant urinary biomaterials

  摘要：

  Herein we report the synthesis, characterisation and hydrolytic release kinetics of a suite of novel, polymerisable ester quinolone conjugates with varying alkenyl chain lengths. Hydrolysis was shown to proceed up to 17-fold faster upon elevation of pH from neutral to pH 9.29, making these conjugates attractive for the development of 'designer' infection-resistant urinary biomaterials exploiting the increase in urine pH reported at the onset of catheter-associated infection to trigger drug release. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.020

文献信息

• Synthesis and release kinetics of polymerisable ester drug conjugates: towards pH-responsive infection-resistant urinary biomaterials
  作者：Colin P. McCoy、Nicola J. Irwin、Christopher Brady、David S. Jones、Gavin P. Andrews、Sean P. Gorman

  DOI：10.1016/j.tetlet.2013.03.020

  日期：2013.5

  Herein we report the synthesis, characterisation and hydrolytic release kinetics of a suite of novel, polymerisable ester quinolone conjugates with varying alkenyl chain lengths. Hydrolysis was shown to proceed up to 17-fold faster upon elevation of pH from neutral to pH 9.29, making these conjugates attractive for the development of 'designer' infection-resistant urinary biomaterials exploiting the increase in urine pH reported at the onset of catheter-associated infection to trigger drug release. (C) 2013 Elsevier Ltd. All rights reserved.