1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-[2-(methylaminomethyl)morpholino]-4-oxoquinoline-3-carboxylic acid | 122910-81-0

• 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-6,8-difluoro-1,4-dihydro-7-[2-(methylaminomethyl)morpholino]-4-oxoquinoline-3-carboxylic acid
• 英文别名: 3-Quinolinecarboxylic acid, 1,4-dihydro-1-cyclopropyl-6,8-difluoro-7-(2-((methylamino)methyl)-4-morpholinyl)-4-oxo-；1-cyclopropyl-6,8-difluoro-7-[2-(methylaminomethyl)morpholin-4-yl]-4-oxoquinoline-3-carboxylic acid
• CAS: 122910-81-0
• 化学式: C₁₉H₂₁F₂N₃O₄
• 分子量: 393.39
• InChiKey: NTBFOBUDTNNTGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  82.1
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-[2-(methylaminomethyl)morpholino]-4-oxoquinoline-3-carboxylic acid 生成 1-Cyclopropyl-6,8-difluoro-7-[2-(methylaminomethyl)morpholin-4-yl]-4-oxoquinoline-3-carboxylic acid;hydrochloride
  参考文献：
  名称：

  ARAKI, KAZUHIKO;KURODA, TSUYOSHI;UEMORI, SATORU;MORIGUCHI, AKIHIKO;IKEDA,+

  摘要：

  DOI：
• 作为产物：
  描述：

  4-苄基-2-(氯甲基)吗啉 在 palladium on activated charcoal 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium iodide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 18.0h， 生成 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-[2-(methylaminomethyl)morpholino]-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Quinolone antimicrobial agents substituted with morpholines at the 7-position. Syntheses and structure-activity relationships

  摘要：

  A series of novel 7-substituted 1-cyclopropyl-6,8-difluoro- 1,4-dihydro-4-oxo-3-quinolinecarboxylic acids have been prepared and tested for antibacterial activities and for convulsive activities in combination with nonsteroidal antiinflammatory drug. Structure-activity relationships revealed that 7-(2-(aminomethyl)morpholino) derivative 28 had a better Gram-positive activity than the reference quinolones, such as ciprofloxacin, norfloxacin, and ofloxacin. Its Gram-negative activity was equipotent with those of norfloxacin and ofloxacin but was inferior to that of ciprofloxacin. In mouse systemic infection models, 28 showed an excellent therapeutic efficacy which might result from the potent antibacterial activity and suitable physicochemical properties. Convulsive activities of 7-morpholino derivatives in combination with nonsteroidal antiinflammatory drug fenbufen or its metabolite biphenylacetic acid markedly diminished as compared to those of 7-piperazino derivatives in the electrophysiological, biochemical, and behavioral experiments. These results suggest that 28 (Y-26611) is a novel quinolone with reduced neurotoxic excitatory adverse reaction.

  DOI：

  10.1021/jm00062a007

文献信息

• Quinolonecarboxylic acid compounds and pharmaceutical use thereof
  申请人：Yoshitomi Pharmaceutical Industries, Ltd.

  公开号：US04889857A1

  公开（公告）日：1989-12-26

  A quinolonecarboxylic acid compound of the formula: ##STR1## wherein R.sup.1 is an alkyl group, a cycloalkyl group, a haloalkyl group, an alkenyl group, mono- or di-alkylamino groups, a phenyl group or a phenyl group substituted by one to three substituents selected from the group consisting of a halogen atom, an alkyl group, an alkoxy group, a hydroxy group, a nitro group or an amino group, R.sup.2 is a hydrogen atom, an alkyl group, a cycloalkyl group, an acyl group or an alkoxycarbonyl group, R.sup.3 is a hydrogen atom, an alkyl group or an aralkyl group, or R.sup.2 and R.sup.3 together with the adjacent nitrogen atom form a heterocyclic ring, R.sup.4 is a hydrogen atom or an alkyl group, R.sup.5 is a hydrogen atom, an alkyl group, an aralkyl group or an ester residue which is readily hydrolyzable in vivo, X is a hydrogen atom, a halogen atom or an alkyl group, n is interger of 1 to 3, and a salt thereof, and pharmaceutical use thereof. The compounds exhibit antibacterial activites and are useful for the treatment of various infectious diseases.

  一种喹诺酮羧酸化合物，其结构式如上：##STR1##其中，R1为烷基、环烷基、卤代烷基、烯基、单或双烷基氨基、苯基或被一个至三个选自卤素、烷基、烷氧基、羟基、硝基或氨基的取代基取代的苯基；R2为氢、烷基、环烷基、酰基或烷氧羰基；R3为氢、烷基或芳烷基，或者R2和R3与相邻的氮原子一起形成杂环；R4为氢或烷基；R5为氢、烷基、芳烷基或体内易水解的酯残基；X为氢、卤素或烷基；n为1至3的整数；及其盐，以及其在医药上的用途。这些化合物具有抗菌活性，可用于治疗各种感染性疾病。
• ARAKI, KAZUHIKO;KURODA, TSUYOSHI;UEMORI, SATORU;MORIGUCHI, AKIHIKO;IKEDA,+
  作者：ARAKI, KAZUHIKO、KURODA, TSUYOSHI、UEMORI, SATORU、MORIGUCHI, AKIHIKO、IKEDA,+

  DOI：——

  日期：——
• ARAKI, KADZUXIKO;KURODA, TAKEHSI;UEHMORI, SATORU;MORIGUTI, AKIXIKO;IKEHDA+
  作者：ARAKI, KADZUXIKO、KURODA, TAKEHSI、UEHMORI, SATORU、MORIGUTI, AKIXIKO、IKEHDA+

  DOI：——

  日期：——
• JPH02138278A
  申请人：——

  公开号：JPH02138278A

  公开（公告）日：1990-05-28
• JPH03148276A
  申请人：——

  公开号：JPH03148276A

  公开（公告）日：1991-06-25