(S)-9-Fluoro-8-(4-hydroxy-piperidin-1-yl)-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid methyl ester | 861114-75-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (S)-9-Fluoro-8-(4-hydroxy-piperidin-1-yl)-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid methyl ester
• 英文别名: methyl (12S)-7-fluoro-8-(4-hydroxypiperidin-1-yl)-12-methyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5,7,9(13)-tetraene-3-carboxylate
• CAS: 861114-75-2
• 化学式: C₂₀H₂₃FN₂O₄
• 分子量: 374.412
• InChiKey: JBQCXZPSPJCSAR-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-9-Fluoro-8-(4-hydroxy-piperidin-1-yl)-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid methyl ester 在 lithium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 49.5h， 生成 (5S)-9-fluoro-6,7-dihydro-8-(4-β-D-2-O-acetylglucopyranosyloxypiperidin-1-yl)-5-methyl-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid
  参考文献：
  名称：

  A Chiral Benzoquinolizine-2-carboxylic Acid Arginine Salt Active against Vancomycin-Resistant Staphylococcus aureus

  摘要：

  There is an urgent medical need for novel antibacterial agents to treat hospital infections, specially those caused by multidrug-resistant Gram-positive pathogens. The need may also be fulfilled by either exploring antibacterial agents having new mechanism of action or expanding known classes of antibacterial drugs. The paper describes a new chemical entity, compound 21, derived from hitherto little known "floxacin". The choice of the entity was made from a series of synthesized prodrugs and salts of the active chiral benzoquinolizine carboxylic acid, S-H-nadifloxacin. The chemistry, physicochemical characteristics, and essential bioprofile of 21 qualifies it for serious consideration as a novel drug entity against hospital infections of multi-drug-resistant Staphylococcus aureus, and its progress up to clinical phase I trials in humans is described.

  DOI：

  10.1021/jm050035f
• 作为产物：
  描述：

  左氧那地沙星 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 4.0h， 以49%的产率得到(S)-9-Fluoro-8-(4-hydroxy-piperidin-1-yl)-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid methyl ester
  参考文献：
  名称：

  A Chiral Benzoquinolizine-2-carboxylic Acid Arginine Salt Active against Vancomycin-Resistant Staphylococcus aureus

  摘要：

  There is an urgent medical need for novel antibacterial agents to treat hospital infections, specially those caused by multidrug-resistant Gram-positive pathogens. The need may also be fulfilled by either exploring antibacterial agents having new mechanism of action or expanding known classes of antibacterial drugs. The paper describes a new chemical entity, compound 21, derived from hitherto little known "floxacin". The choice of the entity was made from a series of synthesized prodrugs and salts of the active chiral benzoquinolizine carboxylic acid, S-H-nadifloxacin. The chemistry, physicochemical characteristics, and essential bioprofile of 21 qualifies it for serious consideration as a novel drug entity against hospital infections of multi-drug-resistant Staphylococcus aureus, and its progress up to clinical phase I trials in humans is described.

  DOI：

  10.1021/jm050035f

文献信息

• A Chiral Benzoquinolizine-2-carboxylic Acid Arginine Salt Active against Vancomycin-Resistant <i>Staphylococcus </i><i>a</i><i>ureus</i>
  作者：Noel J. de Souza、Shrikant V. Gupte、Prasad K. Deshpande、Vijaya N. Desai、Satish B. Bhawsar、Ravindra D. Yeole、Milind C. Shukla、Jacob Strahilevitz、David C. Hooper、Bülent Bozdogan、Peter C. Appelbaum、Michael R. Jacobs、Nitin Shetty、Mahesh V. Patel、Rasendrakumar Jha、Habil F. Khorakiwala

  DOI：10.1021/jm050035f

  日期：2005.8.1

  There is an urgent medical need for novel antibacterial agents to treat hospital infections, specially those caused by multidrug-resistant Gram-positive pathogens. The need may also be fulfilled by either exploring antibacterial agents having new mechanism of action or expanding known classes of antibacterial drugs. The paper describes a new chemical entity, compound 21, derived from hitherto little known "floxacin". The choice of the entity was made from a series of synthesized prodrugs and salts of the active chiral benzoquinolizine carboxylic acid, S-H-nadifloxacin. The chemistry, physicochemical characteristics, and essential bioprofile of 21 qualifies it for serious consideration as a novel drug entity against hospital infections of multi-drug-resistant Staphylococcus aureus, and its progress up to clinical phase I trials in humans is described.