7-(3-Aminomethyl-pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid | 104455-75-6

• 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: 7-(3-Aminomethyl-pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
• 英文别名: 7-[3-(Aminomethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid
• CAS: 104455-75-6
• 化学式: C₁₈H₂₀FN₃O₃
• 分子量: 345.374
• InChiKey: LHOBGVLPYWZLNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  86.9
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-环丙基-6,7-二氟-4-氧代-1,4-二氢喹啉-3-羧酸乙酯 在 盐酸 作用下， 以 吡啶 为溶剂， 反应 18.0h， 生成 7-(3-Aminomethyl-pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
  参考文献：
  名称：

  喹诺酮类抗菌剂。8-取代的喹啉-3-羧酸和1,8-萘啶-3-羧酸的合成及构效关系。

  摘要：

  一系列7,8-二取代的1-环丙基-6-氟喹啉-3-羧酸，7-取代的1-环丙基-6-氟-1,8-萘啶-3-羧酸和10-取代的9-氟吡啶并苯并恶嗪已经制备了-6-羧酸并评估了其抗菌活性。在7-位（苯并恶嗪10-位）检测的侧链包括哌嗪基（g），3-氨基吡咯烷基（a），3-（氨基甲基）吡咯烷基（b）和烷基化的3-（氨基甲基）吡咯烷基（cf）。喹诺酮环系统C-8的变异包括氢，硝基，氨基，氟和氯。8氢喹诺酮和1,8-萘啶上侧链对革兰氏阴性生物的体外活性的相对增强比cf更大，b更大，g更大。由8个取代基赋予取代的喹诺酮核的活性的顺序为：F大于Cl大于萘啶大于H大于苯并恶嗪大于NH2大于NO2。这些趋势在体内得以保留。

  DOI：

  10.1021/jm00400a016

文献信息

• 7-Substituted-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids; 7-substituted-1-cyclopropyl-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acids; their derivatives; and a process for preparing the compounds
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0153163A2

  公开（公告）日：1985-08-28

  Compound of formula where X is CH, CCl, CF, C-OH, CO-alkyl having from one to three carbons, C-NH-alkyl having from one to three carbons, or N; Y is H, F, Cl or Br; R2 is alkyl having from one to four carbon atoms, vinyl, haloalkyl, or hydroxyalkyl having from two to four carbon atoms or cycloalkyl having three to six carbon atoms. Also described are methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufac- ture of the compounds. The compounds are useful as antibacterial agents.

  式中 X 为 CH、CCl、CF、C-OH、具有一至三个碳原子的 CO-烷基、具有一至三个碳原子的 C-NH- 烷基或 N；Y 为 H、F、Cl 或 Br；R2 为具有一至四个碳原子的烷基、具有二至四个碳原子的乙烯基、卤代烷基或羟基烷基或具有三至六个碳原子的环烷基。 还描述了其制造、配制和用于治疗细菌感染的方法，包括描述了用于制造这些化合物的某些新型中间体。 这些化合物可用作抗菌剂。
• Novel antimicrobial lactam-quinolones
  申请人：Norwich Eaton Pharmaceuticals, Inc.

  公开号：EP0366189A2

  公开（公告）日：1990-05-02

  Antimicrobial lactam-quinolone compounds comprising a lactam-containing moiety linked to a quinolone moiety, of the formula: wherein (1) A', A2, A3, R1, R4 and R6 generally form any of a variety of quinolone, naphthyridine or related cyclic moieties known in the art to have animicrobial activity; and (2) R' or R3 contain a linking moiety, linking the quinolone moiety to a lactam-containing moiety having the formula: wherein (3) R10, R11, R12, R13, and R14, together with bonds "a" and "b", form any of a variety of lactam-containing moieties known in the art to have antimicrobial activity; and (4) the linking moiety includes (for example) carbamate, dithiocarbamate, urea, thiourea, isouronium, isothiouronium, guanidine, carbonate, trithiocarbonate, reversed carbamate, xanthate, reversed isouronium, reversed dithiocarbamate, reversed isothiouronium, amine, imine, ammonium, heteroarylium, ether, thioether, phosphone, phosphoramide, phosphate, sulfonamide, ester, thioester, amide, and hydrazide groups.

  抗菌内酰胺-喹诺酮化合物，包括与喹诺酮分子相连的含内酰胺分子，其分子式为 其中 (1) A'、A2、A3、R1、R4 和 R6 通常构成本领域已知的具有抗菌活性的各种喹诺酮、萘啶或相关环状分子中的任一种；以及 (2) R' 或 R3 含有连接基团，将喹诺酮基团与具有以下式子的含内酰胺基团连接起来： 其中 (3) R10、R11、R12、R13 和 R14 与键 "a "和 "b "一起构成本领域已知的具有抗菌活性的各种含内酰胺分子中的任一种；以及 (4) 连接分子包括（例如）氨基甲酸酯、二硫代氨基甲酸酯、脲、硫脲、异乌拉 铵、异硫乌拉铵、胍、碳酸盐、三硫代碳酸盐、反向氨基甲酸酯、黄原酸盐、反向异乌拉 铵、反向二硫代氨基甲酸酯、反向二硫代氨基甲酸酯、反向二硫代氨基甲酸酯、反向二硫代氨基甲酸酯、反向二硫代氨基甲酸酯、反向二硫代氨基甲酸酯、反向二硫代氨基甲酸酯、反转二硫代氨基甲酸酯、反转异硫脲、胺、亚胺、铵、杂芳脲、醚、硫醚、膦、磷酰胺、磷酸盐、磺酰胺、酯、硫酯、酰胺和酰肼基团。
• Novel antimicrobial quinolonyl lactam esters
  申请人：Norwich Eaton Pharmaceuticals, Inc.

  公开号：EP0366641A2

  公开（公告）日：1990-05-02

  Antimicrobial quinolonyl lactam esters comprising a lactam-containing moiety linked, by an ester group, to the 3-carboxy group of a quinolone moiety. These compounds are of the formula: wherein (1) R3, R4, and R5, together with bonds "a" and "b", form certain lactam-containing moieties similar to those known in the art to have antimicrobial activity; and (2) A, R6, R7, and R8 form any of a variety of quinolone or napthyridine structures similar to those known in the art to have antimicrobial activity.

  抗菌喹烯酮内酰胺酯，包含一个通过酯基与喹烯酮分子的 3-羧基相连的含内酰胺分子。这些化合物的结构式如下 其中 (1) R3、R4 和 R5 与键 "a "和 "b "一起形成某些含内酰胺的分子，类似于本领域已知的具有抗菌活性的分子；以及 (2) A、R6、R7 和 R8 形成各种喹诺酮或萘啶结构中的任何一种，类似于本领域已知的具有抗菌活性的结构。
• Novel antimicrobial quinolonyl lactams
  申请人：Norwich Eaton Pharmaceuticals, Inc.

  公开号：EP0366193A2

  公开（公告）日：1990-05-02

  Antimicrobial quinolonyl lactam compounds comprising a lactam-containing moiety linked, by a non-ester linking moiety, to the 3-carboxy group of a quinolone moiety. These compounds are of the formula: wherein (1) R3, R4, and R5, together with bonds "a" and "b", form any of a variety of lactam-containing moieties similar to those known in the art to have antimicrobial activity; (2) A, R6, R7, and R8 form any of a variety of quinolone or naphthyridine structures similar to those known in the art to have antimicrobial activity; and (3) Y, together with R5, form a variety of non-ester linking moieties between the lactam-containing moiety and the quinolone moiety.

  抗菌喹烯酮内酰胺化合物，其包含的内酰胺分子通过非酯连接分子与喹烯酮分子的 3-羧基相连。这些化合物的结构式如下 其中 (1) R3、R4 和 R5，与键 "a "和 "b "一起，构成与本领域已知的具有抗菌活性的含内酰胺分子类似的各种含内酰胺分子中的任何一种； (2) A、R6、R7 和 R8 形成各种喹诺酮或萘啶结构中的任何一种，类似于本领域已知的具有抗菌活性的结构；以及 (3) Y 与 R5 一起在含内酰胺的分子和喹诺酮分子之间形成各种非酯连接分子。
• Novel antimicrobial dithiocarbamoyl quinolones
  申请人：Norwich Eaton Pharmaceuticals, Inc.

  公开号：EP0366643A2

  公开（公告）日：1990-05-02

  Antimicrobial dithiocarbamoyl quinolone compounds of the general formula: wherein (1) A¹, A², A³, R¹, R³, R⁴, and R⁶ form any of a variety of quinolone and related heterocyclic structures similar to those known in the art to have antimicrobial activity; and (2) (1) R¹ is X, R³ is X, or both R¹ and R³ are X; and (2) X is -R¹⁵-N(R¹⁶)(R¹⁷) or -R¹⁵-R¹⁸-N(R¹⁹)(R¹⁷), where (a) (1) R¹⁵ is nil, alkyl, a carbocyclic ring, or a heterocyclic ring; and (2) R¹⁶ is hydrogen; alkyl; alkenyl; a carbocyclic ring; a heterocyclic ring; or (3) when X is R¹⁵-N(R¹⁶)(R¹⁷), R¹⁶ and R¹⁵ may together comprise a heterocyclic ring including the nitrogen atom to which R¹⁵ and R¹⁶ are bonded; (b) R¹⁷ is C(=S)-S-M, where M is a pharmaceutically-­acceptable salt or biohydrolyzable ester; and (c) (1) R¹⁸ is alkyl, a carbocyclic ring, or a heterocyclic ring; and (2) R¹⁹ is hydrogen; alkyl; alkenyl; a carbocyclic ring; a heterocyclic ring; or (3) R¹⁸ and R¹⁹ may together comprise a heterocyclic ring including the nitrogen atom to which R¹⁸ and R¹⁹ are bonded; and pharmaceutically-acceptable salts and biohydrolyzable esters thereof, and hydrates thereof.

  通式如下的二硫代氨基甲酰基喹诺酮类抗菌化合物 其中 (1) A¹、A²、A³、R¹、R³、R⁴ 和 R⁶ 构成各种喹诺酮和相关杂环结构中的任何一种，这些结构与本领域已知的具有抗菌活性的结构相似；以及 (2) (1) R¹ 是 X，R³ 是 X，或 R¹ 和 R³ 都是 X；以及 (2) X 是-R¹⁵-N(R¹⁶)(R¹⁷)或-R¹⁵-R¹⁸-N(R¹⁹)(R¹⁷)，其中 (a) (1) R¹⁵ 是零、烷基、碳环或杂环；且 (2) R¹⁶ 是氢；烷基；烯基；碳环；杂环；或 (3) 当 X 为 R¹⁵-N(R¹⁶)(R¹⁷) 时，R¹⁶ 和 R¹⁵ 可共同组成一个杂环，包括 R¹⁵ 和 R¹⁶ 所键合的氮原子； (b) R¹⁷ 是 C(=S)-S-M，其中 M 是药学上可接受的盐或可生物水解的酯；以及 (c) (1) R¹⁸ 是烷基、碳环或杂环；且 (2) R¹𠞙 是氢；烷基；烯基；碳环；杂环；或 (3) R¹⁸ 和 R¹𠞙 可共同组成一个杂环，包括与 R¹⁸ 和 R¹𠞙 键合的氮原子； 及其药学上可接受的盐和生物可水解酯，以及其水合物。