2-chloro-3-nitro-5,12-dihydro-5-oxobenzothiazolo[3,2-a]quinoline-6-carboxylic acid | 1028202-77-8

• 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-chloro-3-nitro-5,12-dihydro-5-oxobenzothiazolo[3,2-a]quinoline-6-carboxylic acid
• CAS: 1028202-77-8
• 化学式: C₁₆H₇ClN₂O₅S
• 分子量: 374.761
• InChiKey: QYPCDLOBLKXPFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101.92
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-chloro-3-nitro-5,12-dihydro-5-oxobenzothiazolo[3,2-a]quinoline-6-carboxylic acid 、 4-哌啶酮缩乙二醇 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以74%的产率得到2-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)-3-nitro-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
• 作为产物：
  描述：

  ethyl 2-chloro-3-nitro-5,12-dihydro-5-oxobenzothiazolo[3,2-a]quinoline-6-carboxylate 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以94%的产率得到2-chloro-3-nitro-5,12-dihydro-5-oxobenzothiazolo[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