1-cyclopropyl-6-fluoro-1,4-dihydro-7-[3'-hydroxy-1'-azetidinyl]-4-oxo-3-quinolinecarboxylic acid

• 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: 1-cyclopropyl-6-fluoro-1,4-dihydro-7-[3'-hydroxy-1'-azetidinyl]-4-oxo-3-quinolinecarboxylic acid
• 英文别名: 1-cyclopropyl-6-fluoro-7-(3-hydroxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid；1-cyclopropyl-6-fluoro-7-(3-hydroxyazetidin-1-yl)-4-oxoquinoline-3-carboxylic acid
• 化学式: C₁₆H₁₅FN₂O₄
• 分子量: 318.305
• InChiKey: GNVVASBFANKIRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  81.1
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  氮杂环丁烷-3-醇 、 1-环丙基-6,7-二氟-1,4-二氢-4-氧喹啉-3-羧酸 在 吡啶 、 三乙胺 作用下， 反应 3.0h， 以27%的产率得到1-cyclopropyl-6-fluoro-1,4-dihydro-7-[3'-hydroxy-1'-azetidinyl]-4-oxo-3-quinolinecarboxylic acid
  参考文献：
  名称：

  7-Azetidinylquinolones as antibacterial agents. Synthesis and structure-activity relationships

  摘要：

  A series of novel antibacterial quinolones and naphthyridones has been prepared which contain 7-azetidinyl substituents in place of the usual piperazine or aminopyrrolidine groups. These azetidinyl derivatives were evaluated for in vitro activity by determining minimum inhibitory concentrations against a variety of bacteria. In vivo efficacy in the mouse infection model and blood levels in the mouse were determined for several compounds. The influence on the structure-activity relationships of varying substituents in the azetidine ring and at position 8 (CH, CF, CCl, N) and N-1 (ethyl, fluoroethyl, cyclopropyl, tert-butyl, 4-fluorophenyl, and 2,4-difluorophenyl) was also studied. Compounds with outstandingly broad-spectrum activity, particularly against Gram-positive organisms, improved in vivo efficacy, and high blood levels were identified in this work. 7-Azetidinyl-8-chloroquinolones were considered as warranting further development.

  DOI：

  10.1021/jm00059a002
• 作为试剂：
  描述：

  7-氯-6-氟-1-环丙基-1,4-二氢-4-氧-3-喹啉羧酸 、 3-羟基氮杂环丁烷盐酸盐 、 三乙胺 、 溶剂黄146 在 N,N-二甲基甲酰胺 、 1-cyclopropyl-6-fluoro-1,4-dihydro-7-[3'-hydroxy-1'-azetidinyl]-4-oxo-3-quinolinecarboxylic acid 作用下， 以 二甲基亚砜 、 水 为溶剂， 反应 6.0h， 生成 1-cyclopropyl-6-fluoro-1,4-dihydro-7-[3'-hydroxy-1'-azetidinyl]-4-oxo-3-quinolinecarboxylic acid
  参考文献：
  名称：

  Derivatives of 7-(1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic

  摘要：

  本发明涉及新的杂环化合物，它们是7-(1-氮杂环基)-1,4-二氢-4-氧代-3-喹啉羧酸的衍生物，其特点在于它们符合公式(I) ##STR1## 本发明还涉及这些化合物的制备以及它们作为药物的应用。

  公开号：

  US04927926A1

文献信息

• Azetidinyl quinolone carboxylic acids and esters
  申请人：PFIZER INC.

  公开号：EP0314362A2

  公开（公告）日：1989-05-03

  Compounds of the formula wherein R¹ is hydroxy, alkoxy of 1 to 6 carbon atoms, or NR⁴R⁵, wherein R⁴ and R⁵ are independently selected from hydrogen and alkyl of 1 to 6 carbon atoms; R² is hydrogen, hydroxy, alkanoylamino of 1 to 6 carbon atoms, morpholino, halogen, cyano, hydroxyalkyl of 1 to 6 carbon atoms, COOR⁶ wherein R⁶ is hydrogen or alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms or NR⁷R⁸ wherein R⁷ and R⁸ are independently selected from hydrogen, alkyl of 1 to 6 carbon atoms, aminoalkyl of 2 to 6 carbon atoms, alkylaminoalkyl wherein each alkyl group is independently selected from alkyl groups having 2 to 6 carbon atoms, and dialkylamino­alkyl wherein each alkyl group is independently selected from alkyl groups having one to six carbon atoms; and R³ is hydrogen, alkyl of 1 to 6 carbon atoms, phenyl or substituted phenyl wherein the phenyl group may be substituted with one or two substituents selected from the group consisting of alkyl of 1 to 6 carbon atoms, nitro, amino, halogen, (e.g., fluoro, chloro, bromo, or iodo), haloalkyl of 1 or 2 carbon atoms and up to 5 halogen atoms (e.g., fluoro, chloro, bromo or iodo), hydroxyl, or alkoxy of 1 to 6 atoms;and pharmaceutically acceptable salts thereof. The compounds have antibacterial activity.

  式中的化合物 其中 R¹ 是羟基、1 至 6 个碳原子的烷氧基或 NR⁴R⁵，其中 R⁴ 和 R⁵ 独立选自氢和 1 至 6 个碳原子的烷基； R² 是氢、羟基、1 至 6 个碳原子的烷酰氨基、吗啉基、卤素、氰基、1 至 6 个碳原子的羟烷基、COOR⁶（其中 R⁶ 是氢或 1 至 6 个碳原子的烷基）、1 至 6 个碳原子的烷氧基或 NR⁷R⁸（其中 R⁷ 和 R⁸ 独立选自氢）、1至6个碳原子的烷基、2至6个碳原子的氨基烷基、烷基氨基烷基（其中每个烷基独立选自2至6个碳原子的烷基）和二烷基氨基烷基（其中每个烷基独立选自1至6个碳原子的烷基）；和 R³ 是氢、1 至 6 个碳原子的烷基、苯基或取代的苯基，其中苯基可被一个或两个取代基取代，取代基可选自由 1 至 6 个碳原子的烷基、硝基、氨基、卤素（例如：氟、氯、溴）组成的组、1至6个碳原子的烷基、硝基、氨基、卤素（如氟、氯、溴或碘）、1或2个碳原子和多达5个卤素原子（如氟、氯、溴或碘）的卤代烷基、羟基或烷氧基；及其药学上可接受的盐类。这些化合物具有抗菌活性。
• Dérivés des acides 7-(1-azétidinyl)-1,4-dihydro-4-oxoquinoléine-3-carboxyliques, leur préparation et leur application en tant que médicaments
  申请人：LABORATORIOS DEL DR. ESTEVE, S.A.

  公开号：EP0324298B1

  公开（公告）日：1992-12-23
• US4927926A
  申请人：——

  公开号：US4927926A

  公开（公告）日：1990-05-22
• US5039683A
  申请人：——

  公开号：US5039683A

  公开（公告）日：1991-08-13
• Derivatives of 7-(1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic
  申请人：Laboratorios del Dr. Esteve S.A.

  公开号：US04927926A1

  公开（公告）日：1990-05-22

  The present invention relates to new heterocyclic compounds, derivatives of 7-(1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids, characterized in that they correspond to formula (I) ##STR1## The invention also relates to the preparation of these compounds and their applications as medicines.

  本发明涉及新的杂环化合物，即7-(1-氮杂环丙基)-1,4-二氢-4-氧代-3-喹啉羧酸衍生物，其特征在于它们符合以下式（I）##STR1## 本发明还涉及这些化合物的制备以及它们作为药物的应用。