1-环丙基-6,8-二氟-7-(3-甲基哌嗪-1-基)-4-氧代-1,4-二氢喹啉-3-羧酸 | 103460-89-5

• 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-6,8-二氟-7-(3-甲基哌嗪-1-基)-4-氧代-1,4-二氢喹啉-3-羧酸
• 中文别名: 8-氟代加替沙星
• 英文名称: 1-cyclopropyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic acid
• 英文别名: gatifloxacin；AMQ2；F-GTFX；1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid；1-cyclopropyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid；1-Cyclopropyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid；1-cyclopropyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
• CAS: 103460-89-5；337514-35-9
• 化学式: C₁₈H₁₉F₂N₃O₃
• 分子量: 363.364
• InChiKey: ZHKOPMSOBOQYRH-UHFFFAOYSA-N

物化性质

• 熔点：
  222-250.66℃
• 沸点：
  566.9±50.0 °C(Predicted)
• 密度：
  1.447±0.06 g/cm3(Predicted)
• 溶解度：
  水基（轻微溶解），氯仿（轻微溶解，超声处理），DMSO（轻微溶解，加热）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  1-环丙基-6,8-二氟-7-(3-甲基哌嗪-1-基)-4-氧代-1,4-二氢喹啉-3-羧酸 在 potassium cyanide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以57%的产率得到7-(3-methylpiperazin-1-yl)-1-cyclopropyl-6,8-difluoroquinoline-4-one
  参考文献：
  名称：

  Preparation and antibacterial evaluation of decarboxylated fluoroquinolones

  摘要：

  Decarboxylated ciprofloxacin (3) has been reported in the literature to have antibacterial activities against Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, Bacillus subtilis, Enterobacter cloacae, Serratia marcescens and especially potent activity against Escherichia coli. Herein, we report our syntheses of 3 and five additional decarboxylated fluoroquinolones (FQs). We have re-evaluated the antibacterial activity of these FQs. In contrast to previously reported data, none of these decarboxylated fluoroquinolones showed significant antibacterial activity in our assays using both the broth dilution and agar methods. Our study confirmed that the presence of a carboxylic acid group at the 3-position of the fluoroquinolone scaffold is essential for antibacterial activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.060
• 作为产物：
  描述：

  1-环丙基-6,8-二氟-7-(3-甲基哌嗪-1-基)-4-氧代-1,4-二氢喹啉-3-羧酸乙酯 生成 1-环丙基-6,8-二氟-7-(3-甲基哌嗪-1-基)-4-氧代-1,4-二氢喹啉-3-羧酸
  参考文献：
  名称：

  IRIKURA, TSUTOMU;SUDZUEH, SEHJGO;XIRAI, KEHJDZI;ISIDZAKI, TAKAESI

  摘要：

  DOI：

文献信息

• Quinoline derivatives and processes for preparing the same
  申请人：——

  公开号：US05409933A1

  公开（公告）日：1995-04-25

  The present invention relates to novel quinoline derivatives of formula (I): ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, X, Y and Z are defined as in the specification, and pharmaceutically acceptable acid addition salts thereof, and also to processes for preparing these compounds. The present invention also provides an antibacterial composition comprising a compound of formula (I) or its acid addition salt as an active ingredient and pharmaceutically acceptable excipient. The novel quinoline derivatives of the present invention have an excellent antibacterial activity against bacteria or bacteroides.

  本发明涉及具有以下结构的新奎诺林衍生物（I）：其中R1、R2、R3、X、Y和Z如规范中所定义，以及其药学上可接受的酸盐，以及制备这些化合物的方法。本发明还提供一种抗菌组合物，包括式（I）的化合物或其酸盐加合物作为活性成分和药学上可接受的赋形剂。本发明的新奎诺林衍生物对细菌或类杆菌具有出色的抗菌活性。
• Quinolone and naphthyridine derivatives having at the 3-position a group other than a carboxy group, as antibacterials
  申请人：KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY

  公开号：EP0574231A1

  公开（公告）日：1993-12-15

  The present invention relates to novel quinoline derivatives of formula (I): wherein, R₁ is a straight chain or cyclic lower alkyl group having 1 to 3 carbon atoms, a straight chain or cyclic lower alkyl group having 1 to 3 carbon atoms which is substituted with a halogen atom, a phenyl group or a phenyl group substituted with one or two halogen atoms; R₂ is a hydrogen atom, a lower alkyl or amino group; R₃ is a halogen atom or a substituted or unsubstituted heterocyclic group represented by the following formula (A) which contains at least one nitrogen atom as a hetero atom in the ring; wherein, R₆, R₇, R₈ and R₉ are each hydrogen atoms or lower alkyl groups, or two of these groups may form a bond, m and n are 0 or 1, and Ca-Cb may not form a bond, or is single or double bond; X is nitrogen atom or C-R₄ wherein R₄ is hydrogen or halogen atom, or lower alkyl or lower alkoxy group; and Y and Z are each hydrogen atoms, or electron withdrawing groups, for example, ester, cyano, nitro, acyl or substituted acyl, substituted or unsubstituted amide, lower alkylsulfoxy or lower alkylsulfonyl group, and pharmaceutically acceptable acid addition salts thereof, and also to processes for preparing these compounds. The present invention also provides an antibacterial composition comprising a compound of formula (I) or its acid addition salt as an active ingredient and pharmaceutically acceptable excipients. The novel quinoline derivatives of the present invention have an excellent antibacterial activity against bacteria or bacteroides.

  本发明涉及具有以下式（I）的新型喹啉衍生物： 其中， R₁是具有1至3个碳原子的直链或环状较低烷基基团，具有1至3个碳原子的直链或环状较低烷基基团，其上取代有卤素原子，苯基或取代有一或两个卤素原子的苯基； R₂是氢原子，较低烷基或氨基团； R₃是卤素原子或由以下式（A）表示的取代或未取代的杂环基团，该基团至少包含一个氮原子作为环中的杂原子； 其中， R₆、R₇、R₈和R₉分别是氢原子或较低烷基基团，或其中两个基团可以形成键，m和n为0或1，Ca-Cb可能不形成键，或为单键或双键； X是氮原子或C-R₄，其中R₄是氢或卤素原子，或较低烷基或较低烷氧基团； Y和Z分别是氢原子或电子吸引基团，例如酯，氰基，硝基，酰基或取代酰基，取代或未取代酰胺，较低烷基磺氧基或较低烷基磺酰基团，以及其药学上可接受的酸盐，以及制备这些化合物的方法。 本发明还提供了一种抗菌组合物，其包括具有式（I）的化合物或其酸盐形式作为活性成分和药学上可接受的辅料。 本发明的新型喹啉衍生物对细菌或杆菌具有出色的抗菌活性。
• 8-alkoxyquinolonecarboxylic acid and salts thereof
  申请人：Kyorin Pharmaceutical Co., Ltd.

  公开号：US04980470A1

  公开（公告）日：1990-12-25

  Quinolonecarboxylic acid derivatives of the following formula: ##STR1## wherein R indicates a hydrogen atom or lower alkyl group, R.sup.1 indicates a lower alkyl group, R.sup.2 indicates a hydrogen atom, amino group or nitro group, X indicates a halogen atom, and Z indicates a halogen atom, piperazino group, N-methylpiperazino group, 3-methylpiperazino group, 3-hydroxypyrrolidino group, or pyrrolidino group of the following formula, ##STR2## (here, n is 0 or 1, R.sup.3 indicates a hydrogen atom or lower alkyl group, R.sup.4 indicates a hydrogen atom, lower alkyl group and R.sup.5 indicates a hydrogen atom, lower alkyl group, acyl group or alkoxycarbonyl group), the hydrates and pharmaceutically acceptable salts thereof are useful as antibacterial agents.

  喹诺酮羧酸衍生物的化学式如下：##STR1## 其中 R 表示氢原子或较低的烷基基团，R.sup.1 表示较低的烷基基团，R.sup.2 表示氢原子、氨基团或硝基团，X 表示卤素原子，Z 表示卤素原子、哌嗪基团、N-甲基哌嗪基团、3-甲基哌嗪基团、3-羟基吡咯啉基团或吡咯啉基团，如下所示：##STR2##（这里，n 为 0 或 1，R.sup.3 表示氢原子或较低的烷基基团，R.sup.4 表示氢原子、较低的烷基基团，R.sup.5 表示氢原子、较低的烷基基团、酰基基团或烷氧羰基基团），其水合物和药学上可接受的盐被用作抗菌剂。
• Novel heterocyclic antibacterial compounds
  申请人：——

  公开号：US20030181719A1

  公开（公告）日：2003-09-25

  The invention provides heterocyclic organic compounds that inhibit bacterial DNA polymerase IIIC and type II bacterial topoisomerase. The invention further provides compounds that are useful as intermediates in the synthesis of such heterocyclic organic compounds. Syntheses and uses of such heterocyclic organic molecules are also described.

  该发明提供了抑制细菌DNA聚合酶IIIC和类型II细菌拓扑异构酶的杂环有机化合物。该发明还提供了在合成这种杂环有机化合物中作为中间体有用的化合物。该发明还描述了这种杂环有机分子的合成和用途。
• Quinolinecarboxylic acid derivatives
  申请人：KYORIN PHARMACEUTICAL CO., LTD.

  公开号：EP0178388A1

  公开（公告）日：1986-04-23

  57 Quinolonecarboxylic acid derivatives of the following formula, wherein R' is hydrogen atom or lower alkyl group, R2 is hydrogen atom or methyl group and Y is chlorine or fluorine atom, the hydrates and pharmaceutically acceptable salts thereof, are useful as an antibacterial agent.

  57 下式的喹啉羧酸衍生物、 其中 R' 为氢原子或低级烷基，R2 为氢原子或甲基，Y 为氯原子或氟原子，其水合物和药学上可接受的盐类可用作抗菌剂。