7-(3-氨基哌啶-1-基)-1-环丙基-6-氟-8-甲氧基-4-氧代喹啉-3-羧酸 | 127294-64-8

• 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: 7-(3-氨基哌啶-1-基)-1-环丙基-6-氟-8-甲氧基-4-氧代喹啉-3-羧酸
• 中文别名: (3S)-3-(乙酰氧基)-4-(三甲基氨)丁酸酯
• 英文名称: 7-(3-amino-piperidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
• 英文别名: 7-(3-aminopiperidin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid；3-Quinolinecarboxylic acid, 1,4-dihydro-7-(3-amino-1-piperidinyl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-；7-(3-aminopiperidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid
• CAS: 127294-64-8
• 化学式: C₁₉H₂₂FN₃O₄
• 分子量: 375.4
• InChiKey: RWZYKNVFWKZWDX-UHFFFAOYSA-N

物化性质

• 沸点：
  608.8±55.0 °C(Predicted)
• 密度：
  1.431±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  96.1
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  7-(3-aminopiperidin-1-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 在 盐酸 作用下， 以 水 为溶剂， 生成 7-(3-氨基哌啶-1-基)-1-环丙基-6-氟-8-甲氧基-4-氧代喹啉-3-羧酸
  参考文献：
  名称：

  Novel quinolonecarboxylic acid derivatives

  摘要：

  本发明的新型化合物由通式(1)表示：##STR1##其中R1是氢原子或氨基，R2是氟原子或甲氧基，R3是氢原子或含有1至3个碳原子的低级烷基，n是0或1。通式(1)的化合物表现出比已知的喹诺酮类抗生素如氧氟沙星和诺氟沙星更高的抗菌活性和更少的副作用。此外，具有通式(1)的化合物减少了通常伴随6,8-二氟喹啉类抗生素的的光毒性。

  公开号：

  US05051509A1

文献信息

• [EN] RIFAMYCIN IMINO DERIVATIVES EFFECTIVE AGAINST DRUG-RESISTANT MICROBES<br/>[FR] DERIVES DE RIFAMYCINE IMINO EFFICACES CONTRES DES MICROBES PHARMACORESISTANTS
  申请人：CUMBRE INC

  公开号：WO2005070941A1

  公开（公告）日：2005-08-04

  The present invention relates to rifamycin 3-iminomethylenyl (-CH=N-) derivatives having antimicrobial activities, including activities against drug-resistant microorganisms. The claimed rifamycin derivative has a rifamycin moiety covalently linked to a linker through an iminomethylenyl (-CH=N-) group at the C-3 carbon of the rifamycin moiety and the linker is, in turn, covalently linked to a quinolone structure or its pharmacophore within the DNA gyrase and topoisomerase IV inhibitor family. The inventive rifamycins are novel and exhibit activity against both rifampin and ciprofloxacin-resistant microorganisms.

  本发明涉及具有抗微生物活性的利福霉素3-亚甲基亚胺基(-CH=N-)衍生物，包括对耐药微生物的活性。所述的利福霉素衍生物具有一个利福霉素基团，通过亚甲基亚胺基(-CH=N-)在利福霉素基团的C-3碳上与一个连接剂共价连接，而连接剂又与DNA旋转酶和拓扑异构酶IV抑制剂家族中的奎诺酮结构或其药效团共价连接。这种创新的利福霉素是新颖的，并对利福平和环丙沙星耐药微生物表现出活性。
• C-25 carbamate rifamycin derivatives with activity against drug-resistant microbes
  申请人：Combrink Keith

  公开号：US20050256096A1

  公开（公告）日：2005-11-17

  Compounds of the current invention relate to rifamycin derivatives having antimicrobial activities, including activities against drug-resistant microorganisms. More specifically, compounds of the current invention relate to C-25 carbamate derivatives of rifamycin having another functional group or pharmacophore covalently attached to this position through a carbamate linkage. The resulting compounds exert their antimicrobial activity through a dual-function mechanism and therefore exhibit reduced frequency of resistance.

  当前发明的化合物涉及具有抗微生物活性的利福霉素衍生物，包括针对耐药微生物的活性。更具体地说，当前发明的化合物涉及利福霉素的C-25氨基甲酸酯衍生物，通过氨基甲酸酯键连接到该位置的另一个功能基团或药效团。由此产生的化合物通过双重功能机制发挥其抗微生物活性，因此表现出较低的抗药性频率。
• Rifamycin derivatives effective against drug-resistant microbes
  申请人：Ma Zhenkun

  公开号：US20050261262A1

  公开（公告）日：2005-11-24

  Rifamycin derivatives having antimicrobial activities, including activities against drug-resistant microorganisms are claimed in this invention. The inventive rifamycin derivatives are uniquely designed in that they have a rifamycin moiety covalently linked to a linker group through the C-3 carbon of the rifamycin moiety and the linker is, in turn covalently linked to a therapeutic moiety or antibacterial agent/pharmacophore. The therapeutic moiety can be a quinolone, an oxazolidinone, a macrolide, an aminoglycoside, a tetracycline core or a structure/pharmacophore associated with an antibacterial agent.

  本发明涉及具有抗微生物活性的利福霉素衍生物，包括对耐药微生物的活性。本发明的利福霉素衍生物独特地设计在于，它们具有利福霉素基团通过利福霉素基团的C-3碳与连接基团共价连接，并且连接基团进一步与治疗性基团或抗菌剂/药效团共价连接。治疗性基团可以是喹诺酮、噁唑烷酮、大环内酯、氨基糖苷、四环素核心或与抗菌剂相关的结构/药效团。
• Rifamycin imino derivatives effective against drug-resistant microbes
  申请人：Ding Z. Charles

  公开号：US20050209210A1

  公开（公告）日：2005-09-22

  The present invention relates to rifamycin 3-iminomethylenyl (—CH═N—) derivatives having antimicrobial activities, including activities against drug-resistant microorganisms. The claimed rifamycin derivative has a rifamycin moiety covalently linked to a linker through an iminomethylenyl (—CH═N—) group at the C-3 carbon of the rifamycin moiety and the linker is, in turn, covalently linked to a quinolone structure or its pharmacophore within the DNA gyrase and topoisomerase IV inhibitor family. The inventive rifamycins are novel and exhibit activity against both rifampin and ciprofloxacin-resistant microorganisms.

  本发明涉及具有抗微生物活性的利福霉素3-亚甲基亚胺基(—CH═N—)衍生物，包括对耐药微生物的活性。所述利福霉素衍生物具有利福霉素基团通过亚甲基亚胺基(—CH═N—)与连接基团共价连接于利福霉素基团的C-3碳，并且连接基团与DNA酶解酶和拓扑异构酶IV抑制剂家族中的喹诺酮结构或其药效团共价连接。本发明的利福霉素是新颖的，并且对利福平和环丙沙星耐药微生物均有活性。
• The Synthesis, Structure-Activity, and Structure-Side Effect Relationships of a Series of 8-Alkoxy- and 5-Amino-8-alkoxyquinolone Antibacterial Agents
  作者：Joseph P. Sanchez、Rocco D. Gogliotti、John M. Domagala、Stephen J. Gracheck、Michael D. Huband、Josephine A. Sesnie、Michael A. Cohen、Martin A. Shapiro

  DOI：10.1021/jm00022a013

  日期：1995.10

  A series of 1-cyclopropyl-6-fluoro-8-alkoxy (8-methoxy and 8-ethoxy)-quionoline-3-carboxylic acids and 1-cyclopropyl-5-amino-6-fluoro-8-alkoxyquinoline-3-carboxylic acids has been prepared and evaluated for antibacterial activity. In addition, they were also compared to quinolones with classic substitution at C-8 (H, F, Cl) and the naphthyridine nucleus in a phototoxicity and mammalian cell cytotoxicity assay. The series of 8-methoxyquinolones had antibacterial activity against Gram-positive, Gram-negative, and anaerobic bacteria equivalent to the most active 8-substituted compounds (8-F and 8-Cl). There was also a concomitant reduction in several of the potential side effects (i.e., phototoxicity and clonogenicity) compared to the most active quinolones with classic substitution at C-8. The 8-ethoxy derivatives had an even better safety profile but were significantly less active (2-3 dilutions) in the antibacterial assay.