1-cyclopropyl-7-fluoro-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid | 157373-25-6

• 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: 1-cyclopropyl-7-fluoro-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid
• 英文别名: 1-cyclopropyl-7-fluoro-1,4-dihydro-8-methyl-4-oxo-3-quinolinecarboxylic acid；1-cyclopropyl-7-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid；1-cyclopropyl-7-fluoro-8-methyl-4-oxoquinoline-3-carboxylic acid
• CAS: 157373-25-6
• 化学式: C₁₄H₁₂FNO₃
• 分子量: 261.253
• InChiKey: STXGXKMSBSCFDC-UHFFFAOYSA-N

物化性质

• 沸点：
  427.9±45.0 °C(Predicted)
• 密度：
  1.495±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-(7S)-7-t-butoxycarbonylamino-7-methyl-5-azaspiro[2.4]heptane 、 1-cyclopropyl-7-fluoro-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid 在 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 168.0h， 生成
  参考文献：
  名称：

  WO2006/123792

  摘要：

  公开号：
• 作为产物：
  描述：

  ethyl 2-chloro-α-[(dimethylamino)methylene]-4-fluoro-3-methyl-β-oxo-benzenepropanoate 在 盐酸 、 potassium carbonate 作用下， 反应 5.25h， 生成 1-cyclopropyl-7-fluoro-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Potent 6-Desfluoro-8-methylquinolones as New Lead Compounds in Antibacterial Chemotherapy

  摘要：

  In a furtherance of our SAR study on the C-6 position of quinolone antibacterials, a series of 6-desfluoro-8-methylquinolones were synthesized and evaluated for their in vitro antimicrobial activity. As a result of this study, compounds with strong activity against Gram-positive bacteria, including ciprofloxacin-resistant and methicillin-resistant Staphylococcus aureus, were identified. The best Gram-positive antibacterial activity was exhibited by piperidinyl derivative 6c, which was 17 times more potent than ciprofloxacin and displayed extremely high activity against Streptococcus pneumoniae with an MIC value of less than or equal to 0.016 mu g/mL. Thus, we have shown that substituent combinations in the quinolone ring, excluding the C-6 fluorine atom, might produce powerful antibacterial agents.

  DOI：

  10.1021/jm960414w

文献信息

• Dehalogeno compounds
  申请人：——

  公开号：US20040063754A1

  公开（公告）日：2004-04-01

  3-(1-Aminocycloalkyl)pyrrolidinyl-substituted-6-dehalodeno(hydrogen-substituted)quinolon carboxylic acid derivatives having specific substitunets as represented by the following formula (I), its salts, and hydrates thereof exhibit a broad and potent antibacterial activity on gram-negative and gram-positive bacteria, in particular, resistant bacteria typified by gram-positive cocci, including MRSA, PRSP and VRE. Thus these compounds are usable as drugs. 1

  具有特定取代基的3-(1-氨基环烷基)吡咯烷基取代的6-去卤代(氢取代)喹诺酮羧酸衍生物及其盐和水合物，如下式(I)所示，表现出广谱和强效的抗菌活性，对革兰氏阴性菌和革兰氏阳性菌均有效，特别是对革兰氏阳性球菌等耐药菌，包括MRSA、PRSP和VRE有良好的抗菌活性。因此这些化合物可用作药物。
• Dehalogeno-compounds
  申请人：Takahashi Hisashi

  公开号：US20070123560A1

  公开（公告）日：2007-05-31

  3-(1-Aminocycloalkyl)pyrrolidinyl-substituted-6-dehalodeno(hydrogen-substituted)quinolon carboxylic acid derivatives having specific substituents as represented by the following formula (I), its salts, and hydrates thereof exhibit a broad and potent antibacterial activity on gram-negative and gram-positive bacteria, in particular, resistant bacteria typified by gram-positive cocci, including MRSA, PRSP and VRE. Thus these compounds are usable as drugs.

  具有特定取代基的3-(1-氨基环烷基)吡咯烷基取代的6-去卤代（氢取代）喹诺酮羧酸衍生物，其盐和水合物，如以下公式（I）所示，表现出广谱和强效的抗菌活性，对革兰氏阴性和革兰氏阳性细菌均有效，特别是对革兰氏阳性球菌等耐药菌，包括MRSA、PRSP和VRE。因此，这些化合物可用作药物。
• TRI-, TETRA-SUBSTITUTED-3-AMINOPYRROLIDINE DERIVATIVE
  申请人：TAKAHASHI Hisashi

  公开号：US20090253726A1

  公开（公告）日：2009-10-08

  A quinolone synthetic antibacterial agent and a therapeutic agent for an infection which exhibit broad spectrum and strong antibacterial activity for both Gram positive and Gram negative bacteria, and which are also highly safe are provided. The compound provided is represented by formula (I):

  提供了一种喹诺酮合成抗菌剂和治疗感染的药物，具有广谱和强大的抗菌活性，对革兰氏阳性和革兰氏阴性细菌均有作用，并且非常安全。所提供的化合物由式（I）表示。
• 6-H-4-Oxo-3-chinolinecarbonsäure und ihre Analoge als antibakterielle Mittel
  申请人：BAYER AG

  公开号：EP0607825A1

  公开（公告）日：1994-07-27

  Die Erfindung betrifft neue Chinolon- und Naphthyridoncarbonsäurederivate, die in der 6-Position Wasserstoff tragen der allgemeinen Formel I in welcher   Z   für Reste der Strukturen steht, der 6-Position Wasserstoff tragen, Verfahren zu ihrer Herstellung sowie diese enthaltende antibakterielle Mittel und Futterzusatzstoffe.

  本发明涉及新的喹诺酮和萘啶酮羧酸衍生物，其 6 位带氢，通式为 I 其中 Z 代表以下结构的基团 代表结构的残基 的残基、其制备方法以及含有这些残基的抗菌剂和饲料添加剂。
• FLUOROALKYLPYRROLIDINE DERIVATIVE
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP1857453A1

  公开（公告）日：2007-11-21

  This invention relates to a compound represented by the following formula (1) : its salt or a hydrate thereof. R1 represents hydrogen atom, an optionally substituted alkyl group containing 1 to 6 carbon atoms, a cycloalkyl group containing 3 to 6 carbon atoms, or a substituted carbonyl group derived from an amino acid, a dipeptide, or a tripeptide; R2 represents hydrogen atom, an optionally substituted alkyl group containing 1 to 6 carbon atoms, or a cycloalkyl group containing 3 to 6 carbon atoms; R3 represents an alkyl group containing 1 to 6 carbon atoms or a halogen-substituted alkyl group containing 1 to 6 carbon atoms; R4 represents a cycloalkyl group containing 3 to 6 carbon atoms or a halogen-substituted cycloalkyl group containing 3 to 6 carbon atoms; R5 represents hydrogen atom, phenyl group, acetoxymethyl group, pivaloyloxymethyl group, ethoxycarbonyl group, choline group, dimethylaminoethyl group, 5-indanyl group, phthalidyl group, 5-alkyl-2-oxo-1,3-dioxol-4-ylmethyl group, 3-acetoxy-2-oxobutyl group, or a phenylalkyl group comprising an alkylene group containing 1 to 6 carbon atoms and phenyl group; X1 and X2 independently represent hydrogen atom or a halogen atom; and X represents hydrogen atom or a halogen atom. This compound exhibits broad and strong antibacterial activity to both Gram positive and Gram negative bacteria as well as high safety, and therefore, this compound is useful as a quinolone antibacterial drug, and a prophylactic and/or therapeutic drug for an infectious disease.

  本发明涉及下式（1）所代表的化合物： 其盐或其水合物。 R1 代表氢原子、含有 1 至 6 个碳原子的任选取代的烷基、含有 3 至 6 个碳原子的环烷基或由氨基酸、二肽或三肽衍生的取代的羰基； R2 代表氢原子、含有 1 至 6 个碳原子的任选取代的烷基或含有 3 至 6 个碳原子的环烷基； R3 代表含 1-6 个碳原子的烷基或含 1-6 个碳原子的卤代烷基； R4 代表含有 3 至 6 个碳原子的环烷基或含有 3 至 6 个碳原子的卤代环烷基； R5代表氢原子、苯基、乙酰氧甲基、新戊酰氧甲基、乙氧基羰基、胆碱基、二甲基氨基乙基、5-茚基、酞基、5-烷基-2-氧代-1,3-二氧戊环-4-基甲基、3-乙酰氧基-2-氧代丁基、或由含 1 至 6 个碳原子的亚烷基和苯基组成的苯基烷基； X1 和 X2 各自代表氢原子或卤素原子；以及 X 代表氢原子或卤素原子。 该化合物对革兰氏阳性菌和革兰氏阴性菌均具有广泛而强大的抗菌活性，且安全性高，因此，该化合物可用作喹诺酮类抗菌药物，以及传染性疾病的预防和/或治疗药物。