7-chloro-6-fluoro-4-hydroxy-8-nitroquinoline-3-carboxylic acid ethyl ester | 112857-73-5

• 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: 7-chloro-6-fluoro-4-hydroxy-8-nitroquinoline-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 7-chloro-6-fluoro-4-hydroxy-8-nitro-3-quinoline-carboxylate；Ethyl 7-chloro-6-fluoro-4-hydroxy-8-nitro-3-quinolinecarboxylate；ethyl 7-chloro-6-fluoro-8-nitro-4-oxo-1H-quinoline-3-carboxylate
• CAS: 112857-73-5
• 化学式: C₁₂H₈ClFN₂O₅
• 分子量: 314.657
• InChiKey: XNXDVODMEAVNQO-UHFFFAOYSA-N

物化性质

• 沸点：
  440.7±40.0 °C(Predicted)
• 密度：
  1.592±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-chloro-6-fluoro-4-hydroxy-8-nitroquinoline-3-carboxylic acid ethyl ester 在 吡啶 、 calcium nitrite 、 锌 作用下， 以 二氯甲烷 、 二甲基亚砜 、 苯甲醇 为溶剂， 反应 49.0h， 生成 乙基7-氯-8-氰基-1-环丙基-6-氟-4-氧杂-1,4-二氢喹啉-3-羧酸酯
  参考文献：
  名称：

  一种普拉多沙星的制备方法

  摘要：

  本发明属于药物合成技术领域，具体为一种普拉多沙星的制备方法。本发明通过以4‑氟‑3‑氯‑2‑硝基苯胺为原料通过环化，还原等制备普拉多沙星(8‑氰基‑1‑环丙基‑6‑氟‑7‑(八氢化‑6H‑吡咯并[3，4‑b]吡啶‑6‑基)‑4‑氧代‑1,4‑二氢喹啉‑3‑羧酸)，该路线反应原材料廉价易得，合成路线简单，后处理易操作，仅需6步即可实现目标产物普拉多沙星，反应转率化高，反应过程简单易操作，所得产品纯度较高。

  公开号：

  CN108948011A
• 作为产物：
  描述：

  Ethyl 2-(2,4-dichloro-5-fluoro-3-nitro-benzoyl)-3-(2-ethoxycarbonylethylamino)-acrylate 生成 7-chloro-6-fluoro-4-hydroxy-8-nitroquinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  SCHRIEWER, MICHAEL;GROHE, KLAUS

  摘要：

  DOI：

文献信息

• Design, synthesis, structure–activity relationship and antibacterial activity series of novel imidazo fused quinolone carboxamides
  作者：G. Venkat Reddy、S. Ravi Kanth、D. Maitraie、B. Narsaiah、P. Shanthan Rao、K. Hara Kishore、U.S.N. Murthy、B. Ravi、B. Ashok Kumar、T. Parthasarathy

  DOI：10.1016/j.ejmech.2008.07.024

  日期：2009.4

  A series of novel 7,8 and 1,8 imidazo fused quinolone carboxamides are synthesized and evaluated against antibacterial activity. 1,8 Imidazo fused quinolones exhibit moderate antibacterial activity. Molecular modeling studies were carried out to optimize the pharmacophore. Download : Download full-size image

  合成了一系列新颖的7,8和1,8咪唑并稠合的喹诺酮羧酰胺，并评估了其抗菌活性。1,8咪唑并稠的喹诺酮类药物表现出中等的抗菌活性。进行了分子建模研究以优化药效团。 下载：下载全图
• 4-Hydroxy-quinoline-3-carboxylic
  申请人：Bayer Aktiengesellschaft

  公开号：US04870182A1

  公开（公告）日：1989-09-26

  A process for the preparation of a compound of the formula ##STR1## in which Y is a nitrile group, an ester group COOR.sup.1 or an acid amide CONR.sup.2 R.sup.3, R.sup.1, R.sup.2 and R.sup.3 each independently is hydrogen or C.sub.1 -C.sub.4 -alkyl, and R.sup.3 may also be phenyl, and X.sup.2, X.sup.3, X.sup.4 and X.sup.5 each independently is hydrogen, halogen, nitro, cyano, alkyl having 1-3 carbon atoms, alkoxy having 1-3 carbon atoms, alkylmercapto having 1-3 carbon atoms, alkylsulphonyl having 1-3 carbon atoms, or a phenylsulphonyl group which is optionally substituted in the aryl radical, comprising reacting an aminoacrylate of the formula in which X.sup.1 is halogen, a nitro group, an alkoxy, alkoxy, alkylmercapto or alkylsulphonyl group having 1-3 carbon atoms in each case, or an arylsulphonyl group, W is hydrogen or a --CH.sub.2 CH.sub.2 Z radical, Z is is a nitrile group, an ester group COOR.sup.4 or an acid amide group CONR.sup.5 R.sup.6, and R.sup.4, R.sup.5 and R.sup.6 each independently is hydrogen or C.sub.1 -C.sub.4 -alkyl, and R.sup.5 may also be phenyl, with an acid acceptor in an aprotic solvent. Some of the reactants are new, as are the products which are intermediates for antibacterially active 1-alkyl-4-quinolone-3-carboxylic acids.

  一种制备公式为##STR1##的化合物的方法，其中Y是腈基，酯基COOR.sup.1或酸酰胺基CONR.sup.2R.sup.3，R.sup.1、R.sup.2和R.sup.3各自独立地是氢或C.sub.1-C.sub.4-烷基，R.sup.3也可以是苯基，X.sup.2、X.sup.3、X.sup.4和X.sup.5各自独立地是氢、卤素、硝基、氰基、具有1-3个碳原子的烷基、具有1-3个碳原子的烷氧基、具有1-3个碳原子的烷基硫基、具有1-3个碳原子的烷基磺酰基，或者是在芳基上可选择地取代的苯基磺酰基，包括在无水溶剂中与一种酸受体反应的公式为的氨基丙烯酸酯，其中X.sup.1是卤素、硝基、烷氧基、烷氧基、具有1-3个碳原子的烷基硫基或烷基磺酰基，或者是芳基磺酰基，W是氢或-CH.sub.2 CH.sub.2 Z基团，Z是腈基，酯基COOR.sup.4或酸酰胺基CONR.sup.5R.sup.6，R.sup.4、R.sup.5和R.sup.6各自独立地是氢或C.sub.1-C.sub.4-烷基，R.sup.5也可以是苯基，与一种无水溶剂中的酸受体反应。其中一些反应物是新的，产品是抗菌活性1-烷基-4-喹啉酮-3-羧酸的中间体。
• Process for the preparation of 4-hydroxy-quinoline-3-carboxylic acids
  申请人：Bayer Aktiengesellschaft

  公开号：US04804760A1

  公开（公告）日：1989-02-14

  A process for the preparation of a compound of the formula ##STR1## in which Y is a nitrile group, an ester group COOR.sup.1 or an acid amide CONR.sup.2 R.sup.3, R.sup.1, R.sup.2 and R.sup.3 each independently is hydrogen or C.sub.1 -C.sub.4 -alkyl, and R.sup.3 may also be phenyl, and X.sup.2, X.sup.3, X.sup.4 and X.sup.5 each independently is hydrogen, halogen, nitro, cyano, alkyl having 1-3 carbon atoms, alkoxy having 1-3 carbon atoms, alkylmercapto having 1-3 carbon atoms, alkyl-sulphonyl having 1-3 carbon atoms, or a phenylsulphonyl group which is optionally substituted in the aryl radical, comprising reacting an aminoacrylate of the formula in which X.sup.1 is halogen, a nitro group, an alkoxy, alkoxy, alkylmercapto or alkylsulphonyl group having 1-3 carbon atoms in each case, or an arylsulphonyl group, W is hydrogen or a --CH.sub.2 CH.sub.2 Z radical, Z is a nitrile group, an ester group COOR.sup.4 or an acid amide group CONR.sup.5 R.sup.6, and R.sup.4, R.sup.5 and R.sup.6 each independently is hydrogen or C.sub.1 -C.sub.4 -alkyl, and R.sup.5 may also be phenyl, with an acid acceptor in an aprotic solvent. Some of the reactants are new, as are the products which are intermediates for antibacterially active 1-alkyl-4-quinolone-3-carboxylic acids.

  一种制备公式##STR1##中化合物的过程，其中Y是腈基，酯基COOR.sup.1或酸酰胺CONR.sup.2R.sup.3，R.sup.1，R.sup.2和R.sup.3各自独立地是氢或C.sub.1-C.sub.4-烷基，而R.sup.3也可以是苯基，而X.sup.2，X.sup.3，X.sup.4和X.sup.5各自独立地是氢，卤素，硝基，氰基，具有1-3个碳原子的烷基，具有1-3个碳原子的烷氧基，具有1-3个碳原子的烷基硫醇基，具有1-3个碳原子的烷基磺酰基，或者是苯基磺酰基，该苯基磺酰基在芳基中可以选择性地被取代，包括在无极溶剂中用酸受体反应氨基丙酸酯的公式，其中X.sup.1是卤素，硝基，烷氧基，烷氧基，烷基硫醇基或烷基磺酰基，每种情况下都具有1-3个碳原子，或芳基磺酰基，W是氢或--CH.sub.2 CH.sub.2 Z基，Z是腈基，酯基COOR.sup.4或酸酰胺基CONR.sup.5R.sup.6，而R.sup.4，R.sup.5和R.sup.6各自独立地是氢或C.sub.1-C.sub.4-烷基，而R.sup.5也可以是苯基，反应物中有一些是新的，产品是抗菌活性1-烷基-4-喹啉酮-3-羧酸的中间体。
• SCHRIEWER, MICHAEL;GROHE, KLAUS
  作者：SCHRIEWER, MICHAEL、GROHE, KLAUS

  DOI：——

  日期：——
• US4804760A
  申请人：——

  公开号：US4804760A

  公开（公告）日：1989-02-14