ethyl 7-chloro-6-fluoro-1-isopropyl-4-oxo-1,4-dihydroquinoline-3-carboxylate | 97460-14-5

• 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: ethyl 7-chloro-6-fluoro-1-isopropyl-4-oxo-1,4-dihydroquinoline-3-carboxylate
• 英文别名: 3-chloro-4-fluoro aniline；7-chloro-6-fluoro-1-isopropyl-4-oxo-1,4-dihydroquinoline-3-carboxylate；ethyl 7-chloro-6-fluoro-4-oxo-1-propan-2-ylquinoline-3-carboxylate
• CAS: 97460-14-5
• 化学式: C₁₅H₁₅ClFNO₃
• 分子量: 311.74
• InChiKey: RHSNBXZAGPQLEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 7-chloro-6-fluoro-1-isopropyl-4-oxo-1,4-dihydroquinoline-3-carboxylate 在 盐酸 、 nitronium tetrafluoborate 、 tin(ll) chloride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  使用多糖负载的铜纳米粒子通过ipso硝化将 3-羧基-4-喹诺酮类转化为3-硝基-4-喹诺酮类：合成3-羧基-4-喹诺酮类的3-四唑基生物同工异构体作为抗菌剂†

  摘要：

  壳聚糖负载的Cu纳米粒子已经合成，并用于通过ipso硝化反应从3-羧基-4-喹诺酮类化合物合成3-硝基-4-喹诺酮类化合物。与标准环丙沙星相比，4-喹诺酮的合成3-硝基衍生物已成功转化为3-四唑基生物甾醇，其抗菌活性增强。

  DOI：

  10.1039/c5ra26909a
• 作为产物：
  描述：

  2-(2,4-二氯-5-氟苯甲酰基)-3-乙氧基丙烯酸乙酯 在 sodium hydride 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 3.0h， 生成 ethyl 7-chloro-6-fluoro-1-isopropyl-4-oxo-1,4-dihydroquinoline-3-carboxylate
  参考文献：
  名称：

  Fluoronaphthyridines and quinolones as antibacterial agents. 1. Synthesis and structure-activity relationship of new 1-substituted derivatives

  摘要：

  A series of novel 7-piperazinyl-1-substituted-6-fluoroquinolones and naphthyridines have been prepared and their antibacterial activities evaluated. These derivatives are characterized by having alkyl, alkenyl, arylalkyl, cycloalkyl, and cycloalkenyl groups at the 1-position. As a result of this study, derivatives 7 and 26, which are substituted with tert-butyl groups at N-1, were found to possess excellent in vitro and in vivo potency, particularly against Staphylococcus aureus, comparable to that of norfloxacin or ciprofloxacin. Structure-activity relationships of N-1 substituted alkyls and cycloalkyls are also discussed.

  DOI：

  10.1021/jm00123a005

文献信息

• Developing ciprofloxacin analogues against plant DNA gyrase: a novel herbicide mode of action
  作者：Michael D. Wallace、Nidda F. Waraich、Aleksandra W. Debowski、Maxime G. Corral、Anthony Maxwell、Joshua S. Mylne、Keith A. Stubbs

  DOI：10.1039/c7cc09518j

  日期：——

  The development of ciprofloxacin analogues against plant DNA gyrase, a novel herbicidal target, with increased herbicidal activity and diminished antibacterial activity is described.

  描述了对植物DNA旋转酶的环丙沙星类似物的开发，这是一种新的除草靶标，具有增强的除草活性和减弱的抗菌活性。
• [EN] MONOCARBOXYLATE TRANSPORT MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS DE TRANSPORT DES MONOCARBOXYLATES ET LEURS UTILISATIONS
  申请人：NIROGYONE THERAPEUTICS INC

  公开号：WO2016081464A1

  公开（公告）日：2016-05-26

  The invention generally relates to the field of monocarboxylate transport modulators, e.g., monocarboxylate transport inhibitors, and more particularly to new substituted-quinolone compounds, the synthesis and use of these compounds and their pharmaceutical compositions, e.g., in treating, modulating, forestalling and/or reducing physiological conditions associated with monocarboxylate transport activity such as in treating cancer and other neoplastic disorders, inflammatory diseases, disorders of abnormal tissue growth and fibrosis including cardiomyopathy, obesity, diabetes, cardiovascular diseases, tissue and organ transplant rejection, and malaria.

  这项发明通常涉及单羧酸转运调节剂领域，例如单羧酸转运抑制剂，更具体地涉及新的取代喹啉酮化合物，这些化合物的合成和使用以及它们的药物组合物，例如在治疗、调节、预防和/或减少与单羧酸转运活性相关的生理状况，如治疗癌症和其他肿瘤性疾病、炎症性疾病、异常组织生长和纤维化障碍包括心肌病、肥胖症、糖尿病、心血管疾病、组织和器官移植排斥反应以及疟疾。
• Operative conversions of 3-carboxy-4-quinolones into 3-nitro-4-quinolones <i>via ipso</i>-nitration: potential antifilarial agents as inhibitors of <i>Brugia malayi</i> thymidylate kinase
  作者：Chandra S. Azad、Vishal M. Balaramnavar、Imran A. Khan、Pawan K. Doharey、Jitendra K. Saxena、Anil K. Saxena

  DOI：10.1039/c5ra18036h

  日期：——

  An efficient, cost effective and green methodology for ipso nitration in the synthesis of the 3-nitro derivative of 3-carboxy 4-quinolones has been developed by the quantitative use of copper acetate and silver nitrate in water. The observed regioselectivity of nitration is explained by the DFT calculations. Three of these compounds with IC50 values (2.9–3.4 μmol) against Brugia malayi thymidylate

  通过在水中定量使用乙酸铜和硝酸银，已经开发了一种高效，经济，绿色的ipso硝化方法，用于合成3-羧基4-喹诺酮的3-硝基衍生物。DFT计算解释了观察到的硝化区域选择性。这些化合物中的三种对马来酸胸腺嘧啶激酶的IC 50值为（2.9–3.4μmol），可能是良好的抗丝虫剂，这也通过分子对接研究得到了证明。
• Monocarboxylate transport modulators and uses thereof
  申请人：NIROGYONE THERAPEUTICS, INC.

  公开号：US10766863B2

  公开（公告）日：2020-09-08

  The invention generally relates to the field of monocarboxylate transport modulators, e.g., monocarboxylate transport inhibitors, and more particularly to new substituted-quinolone compounds, the synthesis and use of these compounds and their pharmaceutical compositions, e.g., in treating, modulating, forestalling and/or reducing physiological conditions associated with monocarboxylate transport activity such as in treating cancer and other neoplastic disorders, inflammatory diseases, disorders of abnormal tissue growth and fibrosis including cardiomyopathy, obesity, diabetes, cardiovascular diseases, tissue and organ transplant rejection, and malaria.

  本发明一般涉及单羧酸盐转运调节剂领域，如单羧酸盐转运抑制剂，尤其涉及新的取代喹啉酮化合物、这些化合物及其药物组合物的合成和使用，如、治疗、调节、预防和/或减轻与单羧酸盐转运活性相关的生理状况，如治疗癌症和其他肿瘤性疾病、炎症性疾病、组织异常生长和纤维化疾病，包括心肌病、肥胖症、糖尿病、心血管疾病、组织和器官移植排斥反应以及疟疾。
• ITO, YASUO;KATO, XIDEHO;OGAVA, NOBUO;YAMAGISI, TEHRUSATO;EHTTYU, EHJITI;S+
  作者：ITO, YASUO、KATO, XIDEHO、OGAVA, NOBUO、YAMAGISI, TEHRUSATO、EHTTYU, EHJITI、S+

  DOI：——

  日期：——