6-[(3-fluorophenyl)methoxy]-3,4-dihydro-1H-quinolin-2-one | 912645-52-4

• 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: 6-[(3-fluorophenyl)methoxy]-3,4-dihydro-1H-quinolin-2-one
• CAS: 912645-52-4
• 化学式: C₁₆H₁₄FNO₂
• 分子量: 271.291
• InChiKey: DRYCTIFUTSJCJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  6-[(3-fluorophenyl)methoxy]-3,4-dihydro-1H-quinolin-2-one 在 tetraphosphorus decasulfide 、 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 5.0h， 生成 ethyl 7-(3-fluorobenzyloxy)-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline-1-carboxylate
  参考文献：
  名称：

  1-甲酰胺-三唑并[4,3-a]喹啉衍生物的合成及抗惊厥活性

  摘要：

  以6-羟基-3,4-二氢-2(1H)-喹诺酮为起始原料，合成了一系列具有抗惊厥作用的1-甲酰胺-三唑并[4, 3-a]喹啉衍生物(6a-6n)化合物的神经毒性通过最大电休克试验和旋转棒试验计算，腹腔注射昆明小鼠。结果表明，化合物7-(己氧基)-4,5-二氢-[1,2,4]三唑并[4,3-a]喹啉-1-甲酰胺(6d)是活性最高的一种，其活性也最低。毒性。在抗最大电休克效力试验中，中位有效剂量（ED50）为30.1 mg/kg，中位毒性剂量（TD50）为286 mg/kg，保护指数为9.5，高于参考药物卡马西平。防护指数值为6.0。

  DOI：

  10.1007/s12272-010-0502-0
• 作为产物：
  描述：

  6-羟基-3,4-二氢-2(1H)-喹诺酮 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 6-[(3-fluorophenyl)methoxy]-3,4-dihydro-1H-quinolin-2-one
  参考文献：
  名称：

  1-甲酰胺-三唑并[4,3-a]喹啉衍生物的合成及抗惊厥活性

  摘要：

  以6-羟基-3,4-二氢-2(1H)-喹诺酮为起始原料，合成了一系列具有抗惊厥作用的1-甲酰胺-三唑并[4, 3-a]喹啉衍生物(6a-6n)化合物的神经毒性通过最大电休克试验和旋转棒试验计算，腹腔注射昆明小鼠。结果表明，化合物7-(己氧基)-4,5-二氢-[1,2,4]三唑并[4,3-a]喹啉-1-甲酰胺(6d)是活性最高的一种，其活性也最低。毒性。在抗最大电休克效力试验中，中位有效剂量（ED50）为30.1 mg/kg，中位毒性剂量（TD50）为286 mg/kg，保护指数为9.5，高于参考药物卡马西平。防护指数值为6.0。

  DOI：

  10.1007/s12272-010-0502-0

文献信息

• Synthesis and Anti-inflammatory Activity Evaluation of Novel 7-Alkoxy-1-amino-4,5-dihydro[1,2,4]triazole[4,3-a]quinolines
  作者：Xian-Yu Sun、Cheng-Xi Wei、Kyu-Yun Chai、Hu-Ri Piao、Zhe-Shan Quan

  DOI：10.1002/ardp.200700182

  日期：2008.5

  5‐dihydro[1,2,4]triazolo[4,3‐a]quinolin‐1‐amine) and 5i (7‐(p‐chlorobenzyloxy)‐4,5‐dihydro[1,2,4]triazolo[4,3‐a]quinolin‐1‐amine) showed the highest anti‐inflammatory activity (52% and 58% inhibition, respectively, at 2 h pre‐administration) which were comparable to or even slightly more potent than the reference drug ibuprofen (55%). Furthermore, the structure‐activity relationship of these 1,2,4‐triazole

  在这项研究中，使用 6-羟基-3,4-二氢 [1,2,4] 三唑 [4,3-a] 喹啉合成了一系列新型 7-烷氧基-1-氨基-4,5-二氢 [1,2,4] 三唑 [4,3-a] 喹啉。 -2(1H)-喹诺酮类作为起始原料。通过监测这些化合物抑制二甲苯引起的小鼠耳水肿的能力来评估这些化合物的抗炎活性。一些测试化合物表现出显着的活性，化合物 5f（7-（苄氧基）-4,5-二氢 [1,2,4] 三唑并 [4,3-a] 喹啉-1-胺）和 5i（7 - (p - chlorobenzyloxy) -4,5 - dihydro [1,2,4] triazolo [4,3 -a] quinolin - 1-amine) 显示出最高的抗炎活性（分别为 52% 和 58% 抑制，在给药前 2 小时），与参考药物布洛芬 (55%) 相当甚至略强。此外，这些1,2的构效关系，
• Anticonvulsant and toxicity evaluation of some 7-alkoxy-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline-1(2H)-ones
  作者：Hong-Guang Jin、Xian-Yu Sun、Kyu-Yun Chai、Hu-Ri Piao、Zhe-Shan Quan

  DOI：10.1016/j.bmc.2006.06.044

  日期：2006.10

  To further investigate anticonvulsant activity of quinoline derivatives, a series of 7-alkoxy-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline-1(2H)-one derivatives was synthesized starting from 7-hydroxyl-3,4-dihydro-2(1H)-quinoline. In initial (phase I) screening and quantitative (phase II) evaluation, compound 7-benzyloxyl-4,5-dihydro-[1,2,4]thiazolo[4,3-a]quinoline-1(2H)-one (3f) was among the most

  为了进一步研究喹啉衍生物的抗惊厥活性，从起始位置合成了一系列7-烷氧基-4,5-二氢-[1,2,4]三唑并[4,3-a]喹啉-1（2H）-衍生物7-羟基-3,4-二氢-2（1H）-喹啉。在初始（阶段I）筛选和定量（阶段II）评估中，化合物7-苄氧基-4,5-二氢-[1,2,4]噻唑洛[4,3-a]喹啉-1（2H）-（ 3f）是最活跃的，但毒性也最低。在抗MES效能测试中，中位有效剂量（ED（50））为12.3 mg / kg，中位毒性剂量（TD（50））为547.5 mg / kg，保护指数（PI）为44.5，它比原型药物苯妥英钠，苯巴比妥，卡马西平和丙戊酸盐的PI值大得多。选择化合物3f作进一步评估。在III期药理测试中，该化合物的中位催眠剂量（HD（50））和中位致死剂量（LD（50））分别为1204 mg / kg和> 3000 mg / kg，因此，与原型药物相比，其安全性更高。在
• Design, synthesis of 8-alkoxy-5,6-dihydro-[1,2,4]triazino[4,3-a]quinolin-1-ones with anticonvulsant activity
  作者：Xian-Yu Sun、Lei Zhang、Cheng-Xi Wei、Hu-Ri Piao、Zhe-Shan Quan

  DOI：10.1016/j.ejmech.2008.09.003

  日期：2009.3

  A new series of 8-alkoxy-5,6-dihydro-[1,2,4]triazino[4,3-a]quinolin-1-one derivatives were synthesized. Their anticonvulsant activities were evaluated by the maximal electroshock (MES) test, and their neurotoxicities were evaluated by the rotarod neurotoxicity test. The results showed that 8-heptyloxy-5,6-dihydro-[1,2,4]triazino[4,3-a]quinolin-1-one 5t was the most potent with median effective dose

  合成了一系列新的8-烷氧基-5,6-二氢-[1,2,4]三嗪[4,3 - a ]喹啉-1-酮衍生物。通过最大电击（MES）测试评估其抗惊厥活性，并通过旋转脚架神经毒性测试评估其神经毒性。结果显示8-庚氧基-5,6-二氢-[1,2,4]三嗪[4,3 - a ]喹啉-1-酮5t最有效，中位有效剂量（ED 50）值为11.4。 mg / kg，中毒剂量（TD 50）为114.1 mg / kg，提供保护指数（PI = TD 50 / ED 50）值10.0，远大于原型药物卡马西平的PI（PI = 6.4）。为了解释抗惊厥活性的可能机制，在化学诱导的癫痫发作中对化合物5t进行了测试。
• Synthesis and biological evaluation of rhodanine derivatives bearing a quinoline moiety as potent antimicrobial agents
  作者：Meng Guo、Chang-Ji Zheng、Ming-Xia Song、Yan Wu、Liang-Peng Sun、Yin-Jing Li、Yi Liu、Hu-Ri Piao

  DOI：10.1016/j.bmcl.2013.05.082

  日期：2013.8

  Three series of rhodanine derivatives bearing a quinoline moiety (6a-h, 7a-g, and 8a-e) have been synthesized, characterized, and evaluated as antibacterial agents. The majority of these compounds showed potent antibacterial activities against several different strains of Gram-positive bacteria, including multidrug-resistant clinical isolates. Of the compounds tested, 6g and 8c were identified as the most effective with minimum inhibitory concentration (MIC) values of 1 mu g/mL against multidrug-resistant Gram-positive organisms, including methicillin-resistant and quinolone-resistant Staphylococcus aureus (MRSA and QRSA, respectively). None of the compounds exhibited any activity against the Gram-negative bacteria Escherichia coli 1356 at 64 mu g/mL. The cytotoxic activity assay showed that compounds 6g, 7g and 8e exhibited in vitro antibacterial activity at non-cytotoxic concentrations. Thus, these studies suggest that rhodanine derivatives bearing a quinoline moiety are interesting scaffolds for the development of novel Gram-positive antibacterial agents. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis and evaluation of the anti-inflammatory activity of quinoline derivatives
  作者：Xiang Wen、Shi-Ben Wang、Da-Chuan Liu、Guo-Hua Gong、Zhe-Shan Quan

  DOI：10.1007/s00044-015-1323-y

  日期：2015.6

  Three types of quinoline derivatives, quinolin-2-one, 1-oxa-3,5-diaza-anthracen-6-one, and cyclopenta[a]anthracene, were designed and synthesized as potential anti-inflammatory agents. Their anti-inflammatory activities were evaluated using the xylene-induced ear-edema test in mice. Pharmacological analyses showed that compounds 3-(4-methyl-benzyl)-3,4,7,8-tetrahydro-2H,5H-1-oxa-3,5-diaza-anthracen-6-one (3g) and 9-(4-fluoro-phenyl)-5,8,9,10-tetrahydro-4H-7-oxa-2,3,9,11b-tetraaza-cyclopenta[a]anthracene (6d) exhibited the greatest anti-inflammatory activity (63.19 and 68.28 % inhibition, respectively, 30 min after intraperitoneal administration) and were more potent than the reference drug ibuprofen. The peak activity of 3g and 6d was observed 3 h after oral administration, and the compounds exhibited stronger anti-inflammatory activity than ibuprofen at 50 mg/kg at this time point. The most effective compound, 6d (hydrochloride salt), was evaluated in lipopolysaccharide (LPS)-stimulated RAW264.7 mouse macrophages, in which it significantly inhibited LPS-induced production of tumor necrosis factor-alpha and interleukin-6 in a dose-dependent manner.