N-demethylfleroxacin | 79660-71-2

• 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: N-demethylfleroxacin
• 英文别名: fleroxacin；1-(2-fluoroethyl)-6,8-difluoro-7-piperazin-1-yl-quinoline-4(1H)-one-3-carboxylic acid；6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxo-7-(1-piperazinyl)-quinoline-3-carboxylic acid；Demethylfleroxacin；6,8-Difluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid；6,8-difluoro-1-(2-fluoroethyl)-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid
• CAS: 79660-71-2
• 化学式: C₁₆H₁₆F₃N₃O₃
• 分子量: 355.317
• InChiKey: HFMBQTZRNSPHRY-UHFFFAOYSA-N

物化性质

• 沸点：
  561.9±50.0 °C(Predicted)
• 密度：
  1.437±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-chloro-4-nitro-1-(oxiran-2-ylmethyl)-1H-imidazole 、 N-demethylfleroxacin 以 乙醇 为溶剂， 反应 16.0h， 以42%的产率得到7-(4-(3-(2-chloro-4-nitro-1H-imidazol-1-yl)-2-hydroxypropyl)piperazin-1-yl)-6,8-difluoro-1-(2-fluoroethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Design, Synthesis, Antibacterial Evaluation and Docking Study of Novel 2-Hydroxy-3-(nitroimidazolyl)-propyl-derived Quinolone

  摘要：

  A novel series of 2‐hydroxy‐3‐(nitroimidazolyl)‐propyl‐derived quinolones 6a–o were synthesized and evaluated for their in vitro antibacterial activity. Most of the target compounds exhibited potent activity against Gram‐positive strains. Among them, moxifloxacin analog 6n displayed the most potent activity against Gram‐positive strains including S. epidermidis (MIC = 0.06 μg/mL), MSSE (MIC = 0.125 μg/mL), MRSE (MIC = 0.03 μg/mL), S. aureus (MIC = 0.125 μg/mL), MSSA (MIC = 0.125 μg/mL), (MIC = 2 μg/mL). Its activity against MRSA was eightfold more potent than reference drug gatifloxacin. Finally, docking study of the target compound 6n revealed that the binding model of quinolone nucleus was similar to that of gatifloxacin and the 2‐hydroxy‐3‐(nitroimidazolyl)‐propyl group formed two additional hydrogen bonds.

  DOI：

  10.1111/cbdd.12395
• 作为产物：
  描述：

  6,7,8-trifluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxo-3-quinoline carboxylic acid 生成 N-demethylfleroxacin
  参考文献：
  名称：

  IRIKURA, TSUTOMU;KOGA, XIROSI;MURAYAMA, CATOPY

  摘要：

  DOI：

文献信息

• 一种脱N-甲基氟罗沙星的丙烯酮衍生物及其制备方法和应用
  申请人：郑州工业应用技术学院

  公开号：CN111320578A

  公开（公告）日：2020-06-23

  本发明公开了一种脱N‑甲基氟罗沙星的丙烯酮衍生物及其制备方法和应用，采用如下式Ⅰ化学结构通式：式I中，芳香环Ar为苯环或取代苯环或呋喃环或吡啶环。本发明的一种脱N‑甲基氟罗沙星的丙烯酮衍生物，实现了氟喹啉酮骨架与丙烯酮骨架的有效拼合，进而构筑了新的氟喹诺酮“类查尔酮”化合物，从而增加了新化合物的抗肿瘤活性及抗耐药性，并降低对正常细胞的毒副作用，可以作为抗肿瘤活性物质开发全新结构的抗肿瘤药物。
• Penam antibacterial compounds
  申请人：Hoffmann-La Roche Inc.

  公开号：US05159077A1

  公开（公告）日：1992-10-27

  Antibacterial compounds of the formula ##STR1## in which R.sub.1 is a cyclic or secondary acyclic amino group which independently has antibacterial activity: R.sub.2 is hydrogen, lower alkoxy, lower alkylthio or formamido; R.sub.3 is hydrogen or an organic group bonded through carbon, oxygen, sulfur or nitrogen; R.sub.4 is an electronegative acidic group; or R.sub.3 and R.sub.4 together form a heterocycle; and R.sub.5 is a hydrogen or lower alkyl, except when R.sub.3 and R.sub.4 form a heterocycle, in which case R.sub.5 is hydrogen only; and methods of using same.

  公式为##STR1##的抗菌化合物，其中R.sub.1是一个具有抗菌活性的环状或次级无环氨基基团：R.sub.2是氢、低烷氧基、低烷基硫基或甲酰胺基；R.sub.3是氢或通过碳、氧、硫或氮键合的有机基团；R.sub.4是一个电负酸性基团；或者R.sub.3和R.sub.4一起形成一个杂环；R.sub.5是氢或低烷基，除非R.sub.3和R.sub.4形成一个杂环，在这种情况下，R.sub.5仅为氢；以及使用相同方法。
• Cephalosporin antibacterial compounds
  申请人：Hoffmann-La Roche Inc.

  公开号：US05162523A1

  公开（公告）日：1992-11-10

  Antibacterial compounds of the formula ##STR1## in which R.sub.1 is a cyclic or secondary acyclic amino group which independently has antibacterial activity; R.sub.2 is hydrogen, lower alkoxy, lower alkylthio or formamido; R.sub.3 is hydrogen or an organic group bonded through carbon, oxygen, sulfur or nitrogen; R.sub.4 is an electronegative acidic group; or R.sub.3 and R.sub.4 together form a heterocycle; and R.sub.5 is hydrogen or lower alkyl, except when R.sub.3 and R.sub.4 form a heterocycle, in which case R.sub.5 is hydrogen only; and methods of using same.

  该公式中的抗菌化合物为##STR1##其中R.sub.1是具有抗菌活性的环状或次级非环状氨基基团；R.sub.2是氢、较低的烷氧基、较低的烷基硫基或甲酰氨基基团；R.sub.3是氢或通过碳、氧、硫或氮键合的有机基团；R.sub.4是电负酸性基团；或R.sub.3和R.sub.4一起形成一个杂环；R.sub.5是氢或较低的烷基，除非R.sub.3和R.sub.4形成一个杂环，在这种情况下R.sub.5仅为氢；以及使用方法。
• 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。
• Beta-Lactam Derivatives
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0409081A1

  公开（公告）日：1991-01-23

  β-Lactam compounds of the formula in which R₁ is a cyclic or secondary acyclic amino group which independently has antibacterial activity; R₂ is hydrogen, lower alkoxy, lower alkylthio or formamido; R₃ is hydrogen or an organic group bonded through carbon, oxygen, sulfur or nitrogen; R₄ is an electronegative acidic group; or R₃ and R₄ together form a heterocycle; and R₅ is hydrogen or lower alkyl, except when R₃ and R₄ form a heterocycle, in which case R₅ is hydrogen only; and readily hydrolyzable esters and pharmaceutically acceptable salts of these compounds, and hydrates of any of the foregoing. The products have antibacterial activity.

  式中β-内酰胺化合物 其中 R₁ 是独立具有抗菌活性的环状或仲间无环氨基； R₂ 是氢、低级烷氧基、低级烷硫基或甲酰胺基； R₃ 是氢或通过碳、氧、硫或氮键合的有机基团； R₄ 是电负性酸性基团；或 R₃ 和 R₄ 共同形成杂环；以及 R₅ 是氢或低级烷基，除非 R₃ 和 R₄ 构成杂环，在这种情况下，R₅ 仅是氢； 以及这些化合物的易水解酯和药学上可接受的盐，以及上述任何一种化合物的水合物。 这些产品具有抗菌活性。