2-(2-acetamidoethyl)morpholine | 147465-53-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 2-(2-acetamidoethyl)morpholine
• 英文别名: N-(2-morpholin-2-ylethyl)acetamide
• CAS: 147465-53-0
• 化学式: C₈H₁₆N₂O₂
• 分子量: 172.227
• InChiKey: PCLBAIUHBHBQTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-acetamidoethyl)morpholine 在 盐酸 、 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 11.0h， 生成 7-[2-(2-Amino-ethyl)-morpholin-4-yl]-1-cyclopropyl-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid; hydrochloride
  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
• 作为产物：
  描述：

  2-(2-aminoethyl)-4-benzylmorpholine 在 palladium on activated charcoal 一水合肼 作用下， 以 异丙醇 、 甲苯 为溶剂， 反应 4.5h， 生成 2-(2-acetamidoethyl)morpholine
  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

• SUBSTITUTED ALICYCLIC AMINE-CONTAINING MACROCYCLIC IMMUNOMODULATORS
  申请人：ABBOTT LABORATORIES

  公开号：EP0690713A1

  公开（公告）日：1996-01-10
• US5530119A
  申请人：——

  公开号：US5530119A

  公开（公告）日：1996-06-25
• US5561140A
  申请人：——

  公开号：US5561140A

  公开（公告）日：1996-10-01
• [EN] SUBSTITUTED ALICYCLIC AMINE-CONTAINING MACROCYCLIC IMMUNOMODULATORS<br/>[FR] IMMUNOMODULATEURS MACROCYCLIQUES SUBSTITUES CONTENANT DES AMINES ALICYCLIQUES
  申请人：ABBOTT LABORATORIES

  公开号：WO1994021254A1

  公开（公告）日：1994-09-29

  (EN) Compounds having formula (I), and pharmaceutically acceptable salts, esters, amides and prodrugs thereof, wherein one of R104 and R105 is hydrogen, and the other of R104 and R105 is a group having formula (II), as well as pharmaceutically compositions containing such compounds and methods of immunomodulative therapy utilizing the same.(FR) L'invention concerne des composés ayant la formule (I), et les sels, esters, amides et précurseurs de ces composés, acceptables sur le plan pharmaceutique. Dans cette formule, l'un d'entre R104 et R105 est l'hydrogène, et l'autre d'entre R104 et R105 est un radical ayant la formule (II). L'invention concerne également les compositions pharmaceutiques contenant de tels composés et des thérapies immunomodulatrices faisant appel à elles.
• Quinolone antimicrobial agents substituted with morpholines at the 7-position. Syntheses and structure-activity relationships
  作者：Kazuhiko Araki、Tsuyoshi Kuroda、Satoru Uemori、Akihiko Moriguchi、Yoshifumi Ikeda、Fumihiro Hirayama、Yoshito Yokoyama、Eiji Iwao、Takashi Yakushiji

  DOI：10.1021/jm00062a007

  日期：1993.5

  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.