2-chloro-3-fluoro-5,12-dihydro-5-oxobenzothiazolo<3,2-a>quinoline-6-carboxylic acid | 102614-43-7

• 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-fluoro-5,12-dihydro-5-oxobenzothiazolo<3,2-a>quinoline-6-carboxylic acid
• 英文别名: 2-chloro-3-fluoro-5,12-dihydro-5-oxobenzothiazolo[3,2-a]quinoline-6-carboxylic acid；2-Chloro-3-fluoro-5-oxo-[1,3]benzothiazolo[3,2-a]quinoline-6-carboxylic acid
• CAS: 102614-43-7
• 化学式: C₁₆H₇ClFNO₃S
• 分子量: 347.754
• InChiKey: YRLTUWVGJVDHPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-chloro-3-fluoro-5,12-dihydro-5-oxobenzothiazolo<3,2-a>quinoline-6-carboxylic acid 、 N-(1,4-苯并二烷-2-羰基)哌嗪 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以77%的产率得到2-[4-(2,3-Dihydro-1,4-benzodioxine-3-carbonyl)piperazin-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
• 作为产物：
  描述：

  2,4-二氯-5-氟-Β-氧代苯丙酸乙酯 在 sodium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 二乙二醇二甲醚 为溶剂， 反应 78.0h， 生成 2-chloro-3-fluoro-5,12-dihydro-5-oxobenzothiazolo<3,2-a>quinoline-6-carboxylic acid
  参考文献：
  名称：

  苯并噻唑并[3,2-a]喹诺酮类抗菌剂的合成及生物活性。

  摘要：

  描述了一种新型的具有有效抗菌活性的杂环化合物，即2-取代的氨基-3-氟-5,12-二氢-5-氧代苯并噻唑并[3,2-a]喹啉-6-羧酸。该化合物是7-取代的氨基-6-氟-1-芳基-1，4-二氢-4-氧代喹啉-3-羧酸的构象受限的类似物。在2-位分别具有4-甲基哌嗪基和哌嗪基取代的化合物7和10具有与诺氟沙星相当的体外抗菌活性（15）。在2位上具有4-乙酰基哌嗪基取代基的化合物8对革兰氏阳性生物有活性，对革兰氏阴性生物几乎无活性。报道了通过分子内亲核取代环化反应有效且短时间合成这种新型杂环系统的方法。

  DOI：

  10.1021/jm00158a037

文献信息

• CHU D. T. W.; FERNANDES P. B.; PERNET A. G., J. MED. CHEM., 29,(1986) N 8, 1531-1534
  作者：CHU D. T. W.、 FERNANDES P. B.、 PERNET A. G.

  DOI：——

  日期：——
• Synthesis and biological activity of benzothiazolo[3,2-a]quinolone antibacterial agents
  作者：Daniel T. W. Chu、Prabhavathi B. Fernandes、Andre G. Pernet

  DOI：10.1021/jm00158a037

  日期：1986.8

  A new class of heterocyclic compounds with potent antibacterial activity, namely, 2-substituted amino-3-fluoro-5,12-dihydro-5-oxobenzothiazolo[3, 2-a]quinoline-6-carboxylic acids, is described. The compounds are conformationally restricted analogues of 7-substituted amino-6-fluoro-1-aryl-1, 4-dihydro-4-oxoquinoline-3-carboxylic acids. Compounds 7 and 10, having a 4-methylpiperazinyl and a piperazinyl

  描述了一种新型的具有有效抗菌活性的杂环化合物，即2-取代的氨基-3-氟-5,12-二氢-5-氧代苯并噻唑并[3,2-a]喹啉-6-羧酸。该化合物是7-取代的氨基-6-氟-1-芳基-1，4-二氢-4-氧代喹啉-3-羧酸的构象受限的类似物。在2-位分别具有4-甲基哌嗪基和哌嗪基取代的化合物7和10具有与诺氟沙星相当的体外抗菌活性（15）。在2位上具有4-乙酰基哌嗪基取代基的化合物8对革兰氏阳性生物有活性，对革兰氏阴性生物几乎无活性。报道了通过分子内亲核取代环化反应有效且短时间合成这种新型杂环系统的方法。
• 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.