1-环丙基-5-酰胺-6,7,8-三氟-1,4-二氢-4-氧代-3-喹啉羧酸乙酯 | 103772-13-0

• 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
• 中文名称: 1-环丙基-5-酰胺-6,7,8-三氟-1,4-二氢-4-氧代-3-喹啉羧酸乙酯
• 英文名称: ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate
• 英文别名: ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-4(1H)-oxoquinoline-3-carboxylate；ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate；ethyl 1-cyclopropyl-5-amino-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate；Ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-4-oxoquinoline-3-carboxylate
• CAS: 103772-13-0
• 化学式: C₁₅H₁₃F₃N₂O₃
• 分子量: 326.275
• InChiKey: BOFBKJLYZUFZMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  8

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	ethyl 5-(benzylamino)-1-cyclopropyl-6,7,8-trifluoro-4(1H)-oxoquinoline-3-carboxylate	110872-04-3	C22H19F3N2O3	416.4
  1-环丙基-5-硝基-6,7,8-三氟-1,4-二氢-4-氧代-3-喹啉羧酸乙酯	ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-5-nitro-4-oxo-3-quinolinecarboxylate	103772-12-9	C15H11F3N2O5	356.258
  ——	ethyl 1-cyclopropyl-5,6,7,8-tetrafluoro-4(1H)-oxoquinoline-3-carboxylate	107564-02-3	C15H11F4NO3	329.251

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  5-氨基-1-环丙基-6,7,8-三氟-4-氧代-1,4-二氢-3-喹啉羧酸	5-Amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid	103772-14-1	C13H9F3N2O3	298.221
  ——	Ethyl 5-amino-1-cyclopropyl-6,8-difluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate	110871-98-2	C20H24F2N4O3	406.432
  ——	5-Amino-1-cyclopropyl-6,8-difluoro-4-oxo-7-(propan-2-ylamino)quinoline-3-carboxylic acid	1337541-20-4	C16H17F2N3O3	337.326
  ——	5-Amino-1-cyclopropyl-6,8-difluoro-7-(2-morpholin-4-ylethylamino)-4-oxoquinoline-3-carboxylic acid	1337541-21-5	C19H22F2N4O4	408.405
  ——	5-Amino-1-cyclopropyl-6,8-difluoro-7-[2-(2-pyridylamino)ethylamino]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid	——	C20H19F2N5O3	415.399
  ——	5-amino-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid	110236-78-7	C17H18F2N4O3	364.352
  ——	5-amino-1-cyclopropyl-6,8-difluoro-7-(4-methyl-1-piperazinyl)-4(1H)-oxoquinoline-3-carboxylic acid	110236-79-8	C18H20F2N4O3	378.379
  ——	5-amino-1-cyclopropyl-6,8-difluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid	110871-85-7	C18H20F2N4O3	378.379
  ——	5-amino-1-cyclopropyl-6,8-difluoro-7-[(3R)-3-methylpiperazin-1-yl]-4-oxoquinoline-3-carboxylic acid	120379-32-0	C18H20F2N4O3	378.379
  ——	5-amino-1-cyclopropyl-6,8-difluoro-7-[(3S)-3-methylpiperazin-1-yl]-4-oxoquinoline-3-carboxylic acid	120379-33-1	C18H20F2N4O3	378.379

反应信息

• 作为反应物：
  描述：

  1-环丙基-5-酰胺-6,7,8-三氟-1,4-二氢-4-氧代-3-喹啉羧酸乙酯 在 吡啶 、 硫酸 、 溶剂黄146 作用下， 反应 0.84h， 生成 sparfloxacin
  参考文献：
  名称：

  Pyridonecarboxylic acids as antibacterial agents. Part 14. Synthesis and structure-activity relationships of 5-substituted 6,8-difluoroquinolones, including sparfloxacin, a new quinolone antibacterial agent with improved potency

  摘要：

  A series of 5,7-disubstituted 1-cyclopropyl-6,8-difluoro-4(1H)-oxoquinoline-3-carboxylic acids (10-36) were prepared; the C-5 substituent in these compounds comprised halo, hydroxy, mercapto, and amino groups and the C-7 functional group included variously substituted piperazines. In vitro antibacterial screening results indicated that the amino group was optimal among the C-5 substituents. A combination of the C-5 amino group and the C-7 3,5-dimethylpiperazinyl appendage in this series conferred the best overall antibacterial property with lack of adverse drug interactions. Compound 36k [named sparfloxacin, originally AT-4140, 5-amino-1-cyclopropyl-6,8-difluoro-7-(cis-3,5-dimethyl-1-piperazinyl)- 4(1H)-oxoquinoline-3-carboxylic acid] was superior to ciprofloxacin in both in vitro and in vivo potency and hence was selected as a promising candidate for an improved therapeutic agent.

  DOI：

  10.1021/jm00168a018
• 作为产物：
  描述：

  五氟苯甲酰乙酸乙酯 在 palladium 10% on activated carbon 、 氢气 、 sodium hydride 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 甲苯 为溶剂， 145.0 ℃ 、101.33 kPa 条件下， 反应 8.5h， 生成 1-环丙基-5-酰胺-6,7,8-三氟-1,4-二氢-4-氧代-3-喹啉羧酸乙酯
  参考文献：
  名称：

  [EN] QUINOLIN-4-ONE AND 4(1H)-CINNOLINONE COMPOUNDS AND METHODS OF USING SAME
  [FR] COMPOSÉS DE QUINOLIN-4-ONE ET DE 4(1H)-CINNOLINONE ET PROCÉDÉS D'UTILISATION ASSOCIÉS

  摘要：

  本公开涉及喹啉-4-酮和4(1H)-喹啉酮化合物，以及使用它们诱导干/祖细胞支持细胞自我更新的方法，包括诱导干/祖细胞增殖，同时在子细胞中保持分化为组织细胞的能力。

  公开号：

  WO2020163816A1

文献信息

• Aminoquinolones as GSK-3 inhibitors
  申请人：Cociorva Oana

  公开号：US20070254866A1

  公开（公告）日：2007-11-01

  Provided herein are aminoquinolones and pharmaceutically acceptable derivatives thereof. In certain embodiments, provided herein are compounds, compositions and methods for treating, preventing or ameliorating GSK-3 mediated diseases.

  本文提供了氨基喹啉及其药用可接受的衍生物。在某些实施例中，本文提供了用于治疗、预防或改善GSK-3介导疾病的化合物、组合物和方法。
• Quinolone derivatives and salts thereof, preparation processes thereof,
  申请人：Wakunaga Seiyaku Kabushiki Kaisha

  公开号：US05153203A1

  公开（公告）日：1992-10-06

  Antibacterial quinolone derivatives represented by the following formula and salts thereof are disclosed. ##STR1## wherein R.sup.1 meawns a substituted or unsubstituted lower alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted lower alkenyl group or a substituted or unsubstituted phenyl group, R.sup.2 denotes a hydrogen atom or a carboxyl-protecting group, R.sup.3 represents a hydrogen or halogen atom or an amino, mono- or di-(lower alkyl)amino, hydroxyl or lower alkoxyl group, X is a hydrogen or halogen atom, Y means a nitrogen atom or a group C-R.sup.4 in which R.sup.4 is a hydrogen or halogen atom or a lower alkyl or lower alkoxyl group or is a group ##STR2## which forms a ring together with R.sup.1 (i.e., the asterisked carbon atoms are linked to the N(1) atom of the quinolone skeleton), and A denotes a specific N-containing group. Preparation processes of the quinolone derivatives and antibacterial agents containing the same are also disclosed.

  抗菌喹诺酮衍生物及其盐的化学式如下所示。其中，R.sup.1表示取代或未取代的较低烷基基团，取代或未取代的环烷基基团，取代或未取代的较低烯基基团或取代或未取代的苯基基团，R.sup.2表示氢原子或羧基保护基团，R.sup.3表示氢或卤素原子或氨基、单或双-(较低烷基)氨基、羟基或较低烷氧基基团，X是氢或卤素原子，Y表示氮原子或C-R.sup.4基团，其中R.sup.4是氢或卤素原子或较低烷基或较低烷氧基团或是一个组合成环的基团，形成一个环与R.sup.1一起（即星号标记的碳原子与喹诺酮骨架的N(1)原子相连），A表示特定的含氮基团。还披露了喹诺酮衍生物的制备方法和含有它们的抗菌剂。
• Synthesis and antibacterial activity of 4,5,6,7-tetrahydro-thieno[3,2-c]pyridine quinolones
  作者：Brijesh Kumar Srivastava、Manish Solanki、Bhupendra Mishra、Rina Soni、Sanjaya Jayadev、Darshan Valani、Mukul Jain、Pankaj R. Patel

  DOI：10.1016/j.bmcl.2007.01.038

  日期：2007.4

  Synthesis and antibacterial activity of a number of substituted 4,5,6,7-tetrahydro-thieno[3,2-c]pyridine quinolones is reported. The antibacterial activities were evaluated in standard in vitro MIC assay method. Some of the compounds showed in vitro (MIC) antibacterial activity comparable to those of Gatifloxacin, Ciprofloxacin, and Sparfloxacin.

  报道了许多取代的4,5,6,7-四氢噻吩并[3,2-c]吡啶基喹诺酮类化合物的合成和抗菌活性。用标准的体外MIC测定方法评价抗菌活性。一些化合物显示出与加替沙星，环丙沙星和司帕沙星相当的体外（MIC）抗菌活性。
• 4-oxo-1,4-dihydroquinoline-3-carboxylic acid derivative as antibacterial
  申请人：Warner-Lambert Company

  公开号：US04822801A1

  公开（公告）日：1989-04-18

  Novel naphthyridine-, quinoline- and benzoxazinecarboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.

  描述了新型萘啉基、喹啉基和苯并噁嗪羧酸作为抗菌剂的小说，以及它们的制造、配方和用于治疗细菌感染的方法，包括用于制造抗菌剂的某些新型中间体的描述。
• Process for preparing a quinolone-carboxylic acid
  申请人：——

  公开号：US20030166936A1

  公开（公告）日：2003-09-04

  The present invention provides a process for preparing quinolonecarboxylic acid derivatives having the formula (I): 1 wherein R 1 is H, halogen, or amino; R 2 is halogen; R 3 is H, halogen, C 1-4 alkoxyl, or CN; R 4 is selected from the group consisting of C 3-6 cycloalkyl, C 1-4 alkyl, C 1-4 alkoxyC 1-4 alkyl, and C 1-4 alkylaminoC 1-4 alkyl. The invention also provides new acetophenones having the formula (II) that are intermediates for preparing the compound of the formula (I).

  本发明提供了一种制备具有以下式（I）的喹诺酮羧酸衍生物的方法： 其中R1为H、卤素或氨基；R2为卤素；R3为H、卤素、C1-4烷氧基或CN；R4选自C3-6环烷基、C1-4烷基、C1-4烷氧基C1-4烷基和C1-4烷基氨基C1-4烷基的群组。该发明还提供了新的具有以下式（II）的苯乙酮，这些苯乙酮是制备上述式（I）化合物的中间体。