9',10'-difluoro-7'-oxospiro-pyrido<1,2,3-de><1,4>benzoxazine>-6'-carboxylic acid | 113211-52-2

• 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: 9',10'-difluoro-7'-oxospiro-pyrido<1,2,3-de><1,4>benzoxazine>-6'-carboxylic acid
• 英文别名: 9,10-difluoro-7-oxo-2,7-dihydrospiro[[1,4]oxazino[2,3,4-ij]quinoline-3,1'-cyclopropane]-6-carboxylic Acid；6,7-difluoro-10-oxospiro[4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-2,1'-cyclopropane]-11-carboxylic acid
• CAS: 113211-52-2
• 化学式: C₁₄H₉F₂NO₄
• 分子量: 293.227
• InChiKey: PJSHLEDKHBXWOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  9',10'-difluoro-7'-oxospiro-pyrido<1,2,3-de><1,4>benzoxazine>-6'-carboxylic acid 、 N-甲基哌嗪 在 盐酸 作用下， 生成 9'-fluoro-10'-(4-methyl-1-piperazinyl)-7'-oxospiropyrido<1,2,3-de><1,4>benzoxazine>-6'-carboxylic acid monohydrochloride
  参考文献：
  名称：

  Synthesis and bacterial DNA gyrase inhibitory properties of a spirocyclopropylquinolone derivative

  摘要：

  A novel conformationally restricted 1-cyclopropylquinolone (1) that incorporates structural features of both ofloxacin and ciprofloxacin has been prepared. Compound 1 was found to be a DNA gyrase inhibitor having potency similar to ofloxacin but less than ciprofloxacin. The cellular inhibitory and in vivo antibacterial potencies of 1 were found to be less than those of the two reference agents.

  DOI：

  10.1021/jm00117a005
• 作为产物：
  描述：

  ethyl 3-ethoxy-2-(2,3,4,5-tetrafluorobenzoyl)acrylate 在 potassium carbonate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 9',10'-difluoro-7'-oxospiro-pyrido<1,2,3-de><1,4>benzoxazine>-6'-carboxylic acid
  参考文献：
  名称：

  Synthesis and bacterial DNA gyrase inhibitory properties of a spirocyclopropylquinolone derivative

  摘要：

  A novel conformationally restricted 1-cyclopropylquinolone (1) that incorporates structural features of both ofloxacin and ciprofloxacin has been prepared. Compound 1 was found to be a DNA gyrase inhibitor having potency similar to ofloxacin but less than ciprofloxacin. The cellular inhibitory and in vivo antibacterial potencies of 1 were found to be less than those of the two reference agents.

  DOI：

  10.1021/jm00117a005

文献信息

• [EN] SPIROCYCLIC AMINOQUINOLONES AS GSK-3 INHIBITORS<br/>[FR] AMINOQUINOLONES SPIROCYCLIQUES UTILISÉES EN TANT QU'INHIBITEURS DE GSK-3
  申请人：ACTIVX BIOSCIENCES INC

  公开号：WO2009035684A1

  公开（公告）日：2009-03-19

  Provided herein are spirocyclic aminoquinolones of formula I and compositions containing the compounds. The compounds and compositions provided herein are useful in the prevention, amelioration or treatment of GSK- 3 inhibitors mediated diseases. In Formula (I): X1 is O or NR8; A is bond or substituted or unsubstituted C1-C2 alkylene, wherein the substituents when present are selected from one to four Q2 groups; where Q2 is alkyl or haloalkyl; p is 0 or 1; and q is an integer of 0 to 2.

  本文提供了化学式I的螺环氨基喹啉类化合物和含有这些化合物的组合物。本文提供的化合物和组合物可用于预防、改善或治疗GSK-3抑制剂介导的疾病。在化学式(I)中：X1为O或NR8；A为键或取代或未取代的C1-C2烷基，其中取代基在存在时来自于一个到四个Q2基团；其中Q2为烷基或卤代烷基；p为0或1；q为0到2的整数。
• New "ofloxacin" type antibacterial agents. Incorporation of the spiro cyclopropyl group at N-1
  作者：John S. Kiely、Mel C. Schroeder、Josephine C. Sesnie

  DOI：10.1021/jm00118a026

  日期：1988.10

  The first example incorporating a spiro cyclopropyl group into an "ofloxacin" type of quinolone antibacterial agent has been prepared by potassium fluoride mediated ring closure of the hydroxymethyl cyclopropyl intermediate to give 9'-fluoro-7'-oxo-10'-(1-piperazinyl)spiro[cyclopropane-1,3'(2'H)-[7H] pyrido[1,2,3-de][1,4]benzoxazine]-6'-carboxylic acid. Analogues were made by substitution at C-7 by

  通过将氟化甲基介导的羟甲基环丙基中间体的闭环生成9'-氟-7'-氧代10'-（1-），制备了将螺环环丙基掺入“氧氟沙星”型喹诺酮抗菌剂的第一个实例。哌嗪基）螺[环丙烷-1,3'（2'H）-[7H]吡啶基[1,2,3-de] [1,4]苯并恶嗪] -6'-羧酸。通过在C-7处被各种复杂的胺取代来制备类似物。评估这些化合物的抗菌活性。与母体氧氟沙星相比，制备和检查的所有实施例均显示出体外最小抑菌值和体内小鼠保护作用减弱。
• Spirocyclic aminoquinolones as GSK-3 inhibitors
  申请人：Cociorva Oana

  公开号：US08476261B2

  公开（公告）日：2013-07-02

  Provided herein are spirocyclic aminoquinolones of formula I and compositions containing the compounds. The compounds and compositions provided herein are useful in the prevention, amelioration or treatment of GSK-3 inhibitors mediated diseases. In Formula (I): X1 is O or NR8; A is bond or substituted or unsubstituted C1-C2 alkylene, wherein the substituents when present are selected from one to four Q2 groups; where Q2 is alkyl or haloalkyl; p is 0 or 1; and q is an integer of 0 to 2.

  本文提供的是公式I的螺环氨基喹啉和含有该化合物的组合物。本文提供的化合物和组合物在预防、改善或治疗GSK-3抑制剂介导的疾病方面有用。在公式(I)中：X1为O或NR8；A为键或取代或未取代的C1-C2烷基，其中取代基在存在时从1到4个Q2基中选择；其中Q2为烷基或卤代烷基；p为0或1；q为0至2的整数。
• SPIROCYCLIC AMINOQUINOLONES AS GSK-3 INHIBITORS
  申请人：KYORIN PHARMACEUTICALS CO., LTD.

  公开号：US20140005184A1

  公开（公告）日：2014-01-02

  Provided herein are spirocyclic aminoquinolones of formula I and compositions containing the compounds. The compounds and compositions provided herein are useful in the prevention, amelioration or treatment of GSK-3 inhibitors mediated diseases.

  本文提供的是公式I的螺环氨基喹啉和含有这些化合物的组合物。这些化合物和组合物对预防、改善或治疗GSK-3抑制剂介导的疾病是有用的。
• SPIROCYCLIC AMINOQUINOLNES AS GSK-3 INHIBITORS
  申请人：Cociorva Oana

  公开号：US20110034436A1

  公开（公告）日：2011-02-10

  Provided herein are spirocyclic aminoquinolones of formula I and compositions containing the compounds. The compounds and compositions provided herein are useful in the prevention, amelioration or treatment of GSK-3 inhibitors mediated diseases. In Formula (I): X 1 is O or NR 8 ; A is bond or substituted or unsubstituted C 1 -C 2 alkylene, wherein the substituents when present are selected from one to four Q 2 groups; where Q 2 is alkyl or haloalkyl; p is 0 or 1; and q is an integer of 0 to 2.

  本文提供了公式I的螺环氨基喹啉酮和含有该化合物的组合物。本文提供的化合物和组合物在预防、改善或治疗GSK-3抑制剂介导的疾病方面具有用途。在公式(I)中：X1为O或NR8；A为键或取代或未取代的C1-C2烷基，其中取代基在存在时从1到4个Q2基中选择；其中Q2为烷基或卤代烷基；p为0或1；q为0到2的整数。