(-)-6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-<1,3>thiazeto<3,2-a>quinoline-3-carboxylic acid

• 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: (-)-6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-<1,3>thiazeto<3,2-a>quinoline-3-carboxylic acid
• 英文别名: (S)-(-)-6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid；(S)-6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid；(1S)-6-fluoro-1-methyl-4-oxo-7-piperazin-4-ium-1-yl-1H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate
• 化学式: C₁₆H₁₆FN₃O₃S
• 分子量: 349.386
• InChiKey: SUXQDLLXIBLQHW-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  98.2
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (-)-6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-<1,3>thiazeto<3,2-a>quinoline-3-carboxylic acid 在 三乙胺 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 S-(-)-6-fluoro-1-methyl-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid mesylate
  参考文献：
  名称：

  PREPARATION METHOD OF OPTICALLY ACTIVE S-(-)-PRULIFLOXACIN

  摘要：

  公开号：

  EP2524922B1
• 作为产物：
  描述：

  6-氟-7-哌嗪-1-甲基-4-氧-[1,3]硫氮杂环[3,2-a]-喹啉-3-羧酸 在 sodium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 20.0h， 生成 (-)-6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-<1,3>thiazeto<3,2-a>quinoline-3-carboxylic acid
  参考文献：
  名称：

  PREPARATION METHOD OF OPTICALLY ACTIVE S-(-)-PRULIFLOXACIN

  摘要：

  公开号：

  EP2524922B1

文献信息

• PHARMACEUTICALLY ACCEPTABLE SALTS OF ANTI-INFECTION QUINOLONE COMPOUNDS
  申请人：Chen Mao

  公开号：US20110028444A1

  公开（公告）日：2011-02-03

  The invention discloses the pharmaceutically acceptable salts of an optically active quinolone compound useful against infection, specifically the pharmaceutically acceptable salts of (S)-6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid. The pharmaceutically acceptable salts of the present invention are stable and have improved water solubility. They possess higher biological activity, less toxicity for kidney and no irritation to skin and muscle.

  本发明公开了一种用于治疗感染的光学活性喹诺酮化合物的药用可接受盐，具体是(S)-6-氟-1-甲基-4-氧代-7-(1-哌嗪基)-1H，4H-[1,3]噻唑并[3,2-a]喹啉-3-羧酸的药用可接受盐。本发明的药用可接受盐稳定，水溶性改善。它们具有更高的生物活性，对肾脏毒性更小，不刺激皮肤和肌肉。
• Studies on Pyrionecarboxylic Acids. IV. Synthesis and Antibacterial Activity Evaluation of S-(-)- and R-(+)-6-Fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylic Acids.
  作者：Jun SEGAWA、Kenji KAZUNO、Masato MATSUOKA、Isao AMIMOTO、Masakuni OZAKI、Masato MATSUDA、Yoshifumi TOMII、Masahiko KITANO、Masahiro KISE

  DOI：10.1248/cpb.43.1238

  日期：——

  thiazeto [3,2-alpha] quinoline-3- carboxylic acid (NM394, 3) were prepared through optical resolution of their racemic intermediate ( +/- )-1 by high-performance liquid chromatography (HPLC). The absolute configuration at the C-1 position in the thiazeto-quinolone ring of ( - )-3 was confirmed by X-ray analysis ( - )-4 to be S. The in vitro antibacterial activity of ( - )-3 was 2--8 times that of (+)-3

  6-氟-1-甲基-4-氧代-7-（1-哌嗪基）-4H- [1,3]噻嗪并[3,2-α]喹啉-3-羧酸的旋光异构体（NM394，3）通过高效液相色谱（HPLC）对其外消旋中间体（+/-）-1进行光学拆分，制备了这些化合物。X射线分析（-）-4证实（-）-3的噻嗪-喹诺酮环中C-1位置的绝对构型为S。（-）-3的体外抗菌活性为2是（+）-3的-8倍。
• PHARMACEUTICALLY ACCEPTABLE SALTS OF ANTI-INFECTIVE QUINOLONE COMPOUND
  申请人：Guangzhou Baiyunshan Pharmaceutical Co. Ltd. Guangzhou Baiyunshan Pharmaceutica Factory

  公开号：EP2258705B1

  公开（公告）日：2014-06-18
• OPTICALLY ACTIVE COMPOUND OF PRULIFLOXACIN FOR TREATING INFECTION AND PREPARATION METHOD THEREOF
  申请人：Ying Jun

  公开号：US20120302580A1

  公开（公告）日：2012-11-29

  Anti-infection levorotatory optically active compound (S-configuration) of prulifloxacin represented by the following formula (1) and preparation method thereof are disclosed. Said method utilizes levorotatory ulifloxacin as the raw material and the reaction is conducted in organic solvent in the presence of alkaline materials, wherein the reaction temperature is −20° C.˜60° C. and the reaction time is 15 minutes to 24 hours.
• US8501741B2
  申请人：——

  公开号：US8501741B2

  公开（公告）日：2013-08-06