2-[3-(Diethylcarbamoyl)piperidin-1-yl]-3-fluoro-5-oxo-[1,3]benzothiazolo[3,2-a]quinoline-6-carboxylic acid | 1028203-09-9

• 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: 2-[3-(Diethylcarbamoyl)piperidin-1-yl]-3-fluoro-5-oxo-[1,3]benzothiazolo[3,2-a]quinoline-6-carboxylic acid
• CAS: 1028203-09-9
• 化学式: C₂₆H₂₆FN₃O₄S
• 分子量: 495.575
• InChiKey: XMHZITDXDSDONG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N,N-二乙基尼哌丁酰胺 、 2-chloro-3-fluoro-5,12-dihydro-5-oxobenzothiazolo<3,2-a>quinoline-6-carboxylic acid 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以70%的产率得到2-[3-(Diethylcarbamoyl)piperidin-1-yl]-3-fluoro-5-oxo-[1,3]benzothiazolo[3,2-a]quinoline-6-carboxylic acid
  参考文献：
  名称：

  Antimycobacterial activities of novel 2-(sub)-3-fluoro/nitro-5,12-dihydro-5-oxobenzothiazolo[3,2-a]quinoline-6-carboxylic acid

  摘要：

  Various 2-(sub)-3-fluoro/nitro-5,12-dihydro-5-oxobenzothiazolo[3,2-a]quinoline-6-carboxylic acid derivatives were synthesized from 2-aminothiophenol by a five-step reaction, evaluated for in-vitro and in-vivo antimycobacterial activities against Mycobacterium tuberculosis H37Rv (MTB), multi-drug resistant Mycobacterium tuberculosis (MDR-TB), and Mycobacterium smegmatis (MC2), and also tested for the ability to inhibit the supercoiling activity of DNA gyrase from M. smegmatis. Among the thirty-four synthesized compounds, 2-(3-(diethylcarbamoyl)piperidin-1-yl)-)-3-fluoro-5,12-dihydro-5-oxobenzothiazoio[3,2a]quinoline-6-carboxylic acid (71) was found to be the most active compound in vitro with MIC of 0.18 and 0.08 mu M against MTB and MTR-TB, respectively. Compound 71 was found to be 2 and 570 times more potent than isoniazid against MTB and MDR-TB, respectively. In the in-vivo animal model 71 decreased the bacterial load in lung and spleen tissues with 2.78 and 3.12 - log 10 protections, respectively, at the dose of 50 mg/kg body weight. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.016

文献信息

• Antimycobacterial activities of novel 2-(sub)-3-fluoro/nitro-5,12-dihydro-5-oxobenzothiazolo[3,2-a]quinoline-6-carboxylic acid
  作者：Murugesan Dinakaran、Palaniappan Senthilkumar、Perumal Yogeeswari、Arnab China、Valakunja Nagaraja、Dharmarajan Sriram

  DOI：10.1016/j.bmc.2007.11.016

  日期：2008.3.15

  Various 2-(sub)-3-fluoro/nitro-5,12-dihydro-5-oxobenzothiazolo[3,2-a]quinoline-6-carboxylic acid derivatives were synthesized from 2-aminothiophenol by a five-step reaction, evaluated for in-vitro and in-vivo antimycobacterial activities against Mycobacterium tuberculosis H37Rv (MTB), multi-drug resistant Mycobacterium tuberculosis (MDR-TB), and Mycobacterium smegmatis (MC2), and also tested for the ability to inhibit the supercoiling activity of DNA gyrase from M. smegmatis. Among the thirty-four synthesized compounds, 2-(3-(diethylcarbamoyl)piperidin-1-yl)-)-3-fluoro-5,12-dihydro-5-oxobenzothiazoio[3,2a]quinoline-6-carboxylic acid (71) was found to be the most active compound in vitro with MIC of 0.18 and 0.08 mu M against MTB and MTR-TB, respectively. Compound 71 was found to be 2 and 570 times more potent than isoniazid against MTB and MDR-TB, respectively. In the in-vivo animal model 71 decreased the bacterial load in lung and spleen tissues with 2.78 and 3.12 - log 10 protections, respectively, at the dose of 50 mg/kg body weight. (C) 2007 Elsevier Ltd. All rights reserved.