ethyl 1-cyclopropyl-6-fluoro-8-nitro-4-oxo-7-phenylamino-1,4-dihydro-quinoline-3-carboxylate | 1321921-95-2

• 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-cyclopropyl-6-fluoro-8-nitro-4-oxo-7-phenylamino-1,4-dihydro-quinoline-3-carboxylate
• 英文别名: ethyl 7-anilino-1-cyclopropyl-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate
• CAS: 1321921-95-2
• 化学式: C₂₁H₁₈FN₃O₅
• 分子量: 411.389
• InChiKey: XNAWUWWVNLAALN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  103.47
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl 1-cyclopropyl-6-fluoro-8-nitro-4-oxo-7-phenylamino-1,4-dihydro-quinoline-3-carboxylate 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 1-cyclopropyl-6-fluoro-8-nitro-4-oxo-7-phenylamino-1,4-dihydro-quinoline-3-carboxylic acid
  参考文献：
  名称：

  具有对甲硝唑抗幽门螺杆菌的新型抗菌特性的新型硝基氟喹诺酮衍生物的合成。

  摘要：

  根除幽门螺杆菌是预防复发并加速十二指肠溃疡和胃溃疡愈合的主要治疗方法之一。由于幽门螺杆菌临床菌株中出现了抗生素抗性，因此越来越需要使用新发现的抗菌剂与标准方法联合治疗幽门螺杆菌的替代方法。本研究的目的是研究单独使用或与甲硝唑联用时新合成的8-硝基氟喹诺酮衍生物对耐甲硝唑的幽门螺杆菌的作用。根据标准的药敏试验方法和棋盘滴定分析，所有被测化合物均对12株幽门螺杆菌临床菌株表现出有趣的抗菌活性，对化合物3c具有最佳的体外作用。此外，与甲硝唑合用时，还观察到了一些受试化合物的协同和加和活性。此外，在测试的硝基氟喹诺酮衍生物中，化合物3b表现出显着的脲酶抑制活性，IC50为62.5 µg / mL。这些结果表明8-硝基氟喹诺酮衍生物与抗-H结合可能具有有用的作用。幽门螺杆菌药物治疗幽门螺杆菌相关疾病。这些结果表明8-硝基氟喹诺酮衍生物与抗-H结合可能具有有用的作用。幽门螺杆菌药物治疗幽门螺杆菌相关疾

  DOI：

  10.3390/molecules22010071
• 作为产物：
  描述：

  苯胺 、 ethyl 7-chloro-1-cyclopropyl-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate 在 吡啶 作用下， 以 二甲基亚砜 为溶剂， 生成 ethyl 1-cyclopropyl-6-fluoro-8-nitro-4-oxo-7-phenylamino-1,4-dihydro-quinoline-3-carboxylate
  参考文献：
  名称：

  具有对甲硝唑抗幽门螺杆菌的新型抗菌特性的新型硝基氟喹诺酮衍生物的合成。

  摘要：

  根除幽门螺杆菌是预防复发并加速十二指肠溃疡和胃溃疡愈合的主要治疗方法之一。由于幽门螺杆菌临床菌株中出现了抗生素抗性，因此越来越需要使用新发现的抗菌剂与标准方法联合治疗幽门螺杆菌的替代方法。本研究的目的是研究单独使用或与甲硝唑联用时新合成的8-硝基氟喹诺酮衍生物对耐甲硝唑的幽门螺杆菌的作用。根据标准的药敏试验方法和棋盘滴定分析，所有被测化合物均对12株幽门螺杆菌临床菌株表现出有趣的抗菌活性，对化合物3c具有最佳的体外作用。此外，与甲硝唑合用时，还观察到了一些受试化合物的协同和加和活性。此外，在测试的硝基氟喹诺酮衍生物中，化合物3b表现出显着的脲酶抑制活性，IC50为62.5 µg / mL。这些结果表明8-硝基氟喹诺酮衍生物与抗-H结合可能具有有用的作用。幽门螺杆菌药物治疗幽门螺杆菌相关疾病。这些结果表明8-硝基氟喹诺酮衍生物与抗-H结合可能具有有用的作用。幽门螺杆菌药物治疗幽门螺杆菌相关疾

  DOI：

  10.3390/molecules22010071

文献信息

• Antibacterial and Anticancer Properties of New Fluoroquinolones
  作者：Maha R. Al Rimawi、Yusuf M. Al-Hiari、Amal G. Al-Bakri、Sanaa K. Bardaweel

  DOI：10.14233/ajchem.2020.22413

  日期：2020.1.15

  Fluoroquinolones are clinically successful antibacterial agents. In this work a series of novel 7-substituted anilino-8-nitrofluoroquinolone esters (3-9), acids (10-16) and 8-amino reduced derivatives (17-23) of the later compounds were successfully prepared and characterized using spectroscopic techniques. All the compounds tested (10-23) showed good antibacterial activity against both Gram-positive and Gram- negative standard bacterial strains. Interestingly, 8-amino reduced derivatives (17-22) were more active against both standard strains than their 8-nitro acid analogues (10-15). Moreover, some targeted compounds have shown reasonable activity mainly against resistant gram positive bacteria. In particular compounds 10, 12 and 16 displayed a potent activity against methicillin resistant S. aureus (MRSA) with MIC values of 4.7, 2.3 and 1.2 μg/mL, respectively. Lipophilicity could be a plausible explanation of such higher activity against the gram positive resistant strain (MRSA). Biological screening of cytotoxic activity against five cancer cell lines using an in vitro cell culture system was achieved for all tested compounds. These derivatives have shown weak activity for most of them. Interestingly, more lipophilic nitroacids (10-15) were more active than their analogous reduced acids (17-22).

  氟喹诺酮是临床上成功的抗菌药物。在这项工作中，一系列新颖的7-取代苯胺基-8-硝基氟喹诺酮酯（3-9）、酸（10-16）和后一类化合物的8-氨基还原衍生物（17-23）成功制备并利用光谱技术进行表征。所有测试的化合物（10-23）对革兰氏阳性和革兰氏阴性标准细菌菌株显示出良好的抗菌活性。有趣的是，8-氨基还原衍生物（17-22）对两种标准菌株的活性均高于它们的8-硝基酸类似物（10-15）。此外，一些目标化合物显示出对耐甲氧西林金黄色葡萄球菌（MRSA）的合理活性。特别是化合物10、12和16对MRSA表现出强大的活性，MIC值分别为4.7、2.3和1.2微克/毫升。脂溶性可能是对抗革兰氏阳性耐药菌株（MRSA）具有较高活性的一个合理解释。通过体外细胞培养系统对五种癌细胞系的细胞毒活性进行生物筛选，所有测试的化合物均取得了成果。这些衍生物大多表现出较弱的活性。有趣的是，更脂溶性的硝基酸（10-15）比它们的类似还原酸（17-22）更活跃。
• Synthesis of 1,2,3-Triazolo[4,5-h]quinolone Derivatives with Novel Anti-Microbial Properties against Metronidazole Resistant Helicobacter pylori
  作者：Mohammad Abu-Sini、Amal Mayyas、Nehaya Al-Karablieh、Rula Darwish、Yusuf Al-Hiari、Talal Aburjai、Shereen Arabiyat、Luay Abu-Qatouseh

  DOI：10.3390/molecules22050841

  日期：——

  eradication of H. pylori infection can prevent relapse and accelerate the healing of gastric and duodenal ulcers as well as regression of malignancy. Due to the increasing emergence of antibiotic resistance among clinical isolates of H. pylori, alternative approaches using newly discovered antimicrobial agents in combination with the standard antibiotic regimens for the treatment of H. pylori are of

  幽门螺杆菌感染可导致胃炎、消化性溃疡和粘膜相关淋巴组织 (MALT) 淋巴瘤的发展。治疗和根除 H. pylori 感染可以防止复发并加速胃和十二指肠溃疡的愈合以及恶性肿瘤的消退。由于 H. pylori 临床分离株中抗生素耐药性的出现日益增加，使用新发现的抗微生物剂结合标准抗生素方案治疗 H. pylori 的替代方法非常重要。本研究的目的是研究新合成的 8-氨基 7-取代氟喹诺酮及其相应的环化三唑并衍生物单独或与甲硝唑联合使用时对甲硝唑耐药幽门螺杆菌的影响。基于标准的抗菌药敏试验方法和棋盘滴定法，所有被测化合物均显示出对 12 种临床幽门螺杆菌的抗菌活性，其中化合物 4b 和 4c 的体外效果最佳。部分抑制浓度 (FIC) 平均值在第 5 组的所有化合物中显示出协同模式。此外，当与甲硝唑组合时，观察到第 4 组的一些测试化合物的加和活性。相比之下，测试化合物没有显示出显着的脲酶抑制活性。这些结果支持新的氟喹诺酮衍生物与抗
• Synthesis and antibacterial activity of novel 7-haloanilino-8-nitrofluoroquinolone derivatives
  作者：Yusuf M. Al-Hiari、Amjad M. Qandil、Rufaida M. Al-Zoubi、Muhammed H. Alzweiri、Rula M. Darwish、Ghassan F. Shattat、Tariq M. Al-Qirim

  DOI：10.1007/s00044-011-9692-3

  日期：2012.8

  The synthesis of new 7-(halophenylamino)-1-cyclopropyl-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid derivatives is described. Substitution of quinolonic compound 1a with chloro and fluoro aniline derivatives at position 7 produced target compounds 2-9 with relatively low yields. Alternatively, the product of correspondent carboxylate ester 1b subsequent with acid hydrolysis produced satisfactory yield. The prepared targets have shown interesting antibacterial properties against standard and resistant gram-positive strains. In particular, 2-chloro and 3-chloro aniline derivatives (3 and 4) depict MIC values of 6.7 and 0.9 mu g/ml, respectively against standard S. aureous. Both compounds showed good activity against resistant strains of S. aureous.
• Antilipase and antiproliferative activities of novel fluoroquinolones and triazolofluoroquinolones
  作者：Shereen Arabiyat、Violet Kasabri、Yusuf Al-Hiari、Yasser K. Bustanji、Rabab Albashiti、Ihab M. Almasri、Dima A. Sabbah

  DOI：10.1111/cbdd.13049

  日期：2017.12

  Fluoroquinolones (FQs) have been identified recently as potent inhibitors of pancreatic lipase (PL). The aim of this study was to synthesize novel FQs and triazolofluoroquinolones (TFQs) and to evaluate them in vitro with respect to their antilipolytic efficacy and potency properties. The PL‐IC50 values of 12 FQs and TFQs (3 (a–c)–6 (a–c)) were in the range of 12.5–189.1 μm. These values are further supported by docking studies. The suggested association between obesity and colorectal cancer initiated the evaluation of antiproliferative activity of the new FQs and TFQs against a panel of obesity‐related colorectal cells (HT29, HCT116, SW620 CACO2, and SW480). Sulforodamine B colorimetric assay revealed that some derivatives exhibited unselective cytotoxicity against HT29, HCT116, SW620 CACO2, and SW480. Remarkably, FQ 4a's selective cytotoxicity against HCT116 was found valuable with IC50 value of 4.2 μm which exceeds that of cisplatin with a substantial selective cytotoxicity in periodontal ligament fibroblasts. In conclusion, FQ and TFQ derivatives may unveil new antiobesity and anticancer agents in the future.