ethyl 1-benzyl-7-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate | 70479-46-8

• 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: ethyl 1-benzyl-7-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate
• 英文别名: Ethyl 1-benzyl-7-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate；ethyl 1-benzyl-7-chloro-6-fluoro-4-oxoquinoline-3-carboxylate
• CAS: 70479-46-8
• 化学式: C₁₉H₁₅ClFNO₃
• 分子量: 359.784
• InChiKey: VAKBWBGHUCFAIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 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 1-benzyl-7-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate 在 水 、 sodium hydroxide 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成 1-benzyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Developing ciprofloxacin analogues against plant DNA gyrase: a novel herbicide mode of action

  摘要：

  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。

  DOI：

  10.1039/c7cc09518j
• 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 1-benzyl-7-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-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

• Structure-activity relationships of antibacterial 6,7- and 7,8-disubstituted 1-alkyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids
  作者：Hiroshi Koga、Akira Itoh、Satoshi Murayama、Seigo Suzue、Tsutomu Irikura

  DOI：10.1021/jm00186a014

  日期：1980.12

  Previous quantitative and qualitative structure-activity studies in antibacterial monosubstituted 1-ethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids prompted us to synthesize the 6,7,8-polysubstituted compounds. In this paper, the preparation and antibacterial activity of the 6,7- and 7,8-disubstituted compounds and their derivatives are described. Among these compounds, 1-ethyl-6-fluoro-1,4-di

  先前在抗菌单取代的1-乙基-1,4-二氢-4-氧代喹啉3-羧酸中进行的定量和定性结构活性研究促使我们合成了6,7,8-多取代的化合物。在本文中，描述了6,7-和7,8-二取代化合物及其衍生物的制备和抗菌活性。在这些化合物中，1-乙基-6-氟-1,4-二氢-4-氧代-7-（1-哌嗪基）喹啉-3-羧酸（34）具有许多显着的活性，并且比草酸（ 84）对抗革兰氏阳性和革兰氏阴性细菌。讨论了构效关系。
• [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。
• Synthesis of 6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid derivatives as potential antimicrobial agents
  作者：Natesh Rameshkumar、Mohan Ashokkumar、Ekambaram Harihara Subramanian、Raju Ilavarasan、Seshaiah Krishnan Sridhar

  DOI：10.1016/s0223-5234(03)00151-x

  日期：2003.11

  antibacterial activity (ED50) against E. coli was 50-160 mg kg(-1) in the order of 7<9<8<10. 1-ethyl-6-fluoro-7-(2,5-dioxo-piperazin-1-yl)1,4-dihydro-4-oxo-quinoline-3-carboxylic acid (7) was found to exhibit the most potent in vitro antimicrobial activity with MIC of 4.1, 3.1, 3.1, 2.4, 1, 1, 25 and >100 microg mL(-1) against Staphylococcus aureus, Staphylococcus epidermidis, Micrococcus luteus, Bacillus cereus

  在本研究中，合成了一系列的1-乙基/苄基-6-氟-7-（取代的哌嗪-1-基）1,4-二氢-4-氧代喹啉-3-羧酸，并通过红外光谱对其进行了表征。 ，1 H-NMR，质谱和元素分析。通过纸盘扩散法评估了化合物的体外抗菌和抗真菌活性。还通过琼脂条纹稀释法确定化合物的最小抑制浓度（MIC）。还通过小鼠保护试验评估了化合物对大肠杆菌的体内抗菌活性。所有化合物均显示出显着的抗菌和弱真菌活性。体内对大肠杆菌的抗菌活性（ED50）为50-160 mg kg（-1），顺序为7 <9 <8 <10。1-乙基-6-氟-7-（2,5-二氧-哌嗪-1-基）1，
• Synthesis, Characterization and Pharmacological Studies of Some Substituted Fluoroquinolones
  作者：FAIZ MOHD. ABDULLAH、ARVIND KUMAR SINGH

  DOI：10.13005/ojc/290231

  日期：2013.6.30

  Certain N-1 substituted fluoroquinolonic derivatives were synthesized and evaluated for antimicrobial and antioxidant activities. N-1 alkyl/ aryl/ aryl sulphonyl substituted derivatives of the title compounds have been synthesized to identify newer fluoroquinolones which have better efficacy, lesser side effects and well tolerability. The biological evaluation of the synthesized fluoroquinolone derivatives

  合成了某些N-1取代的氟喹诺酮衍生物，并评估了其抗菌和抗氧化活性。合成了标题化合物的N-1烷基/芳基/芳基磺酰基取代的衍生物，以鉴定具有较好功效，较小副作用和良好耐受性的新型氟喹诺酮。使用琼脂井扩散法对合成的氟喹诺酮衍生物进行生物学评估，发现化合物FIETH，FII-SUL，FIII-ATY，FIV-BZO和FV-BZY对革兰氏阳性和革兰氏阴性细菌均具有活性具有与标准药物即氧氟沙星10mg / ml相当的活性。N-1取代的部分对金黄色葡萄球菌，肺炎克雷伯氏菌和大肠埃希氏菌的活性最高，浓度为100-150μg/ ml，对菌株的活性较低。其次，通过这四种方法的DPPH自由基清除法，过氧化氢自由基清除法，一氧化氮测定法和还原功率测定法，抗氧化剂活性显示出更好的活性。所有合成的化合物都显示出更好的抗氧化活性，并且在第四种方法中，结果大部分能够降低合成的化合物的功率活性。
• 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。