(3R)-3-[1-(tert-butoxycarbonyl-N-methylamino)cyclopropan-1-yl]pyrrolidine | 431058-53-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3R)-3-[1-(tert-butoxycarbonyl-N-methylamino)cyclopropan-1-yl]pyrrolidine
• 英文别名: 3-(R)-[1-[N-(tert-butoxycarbonyl)-N-(methyl)amino]cyclopropyl]pyrrolidine；3-(R)-[1-(tert-butoxycarbonylmethylamino)cyclopropyl]pyrrolidine；1,1-Dimethylethyl N-methyl-N-[1-(3R)-3-pyrrolidinylcyclopropyl]carbamate；tert-butyl N-methyl-N-[1-[(3R)-pyrrolidin-3-yl]cyclopropyl]carbamate
• CAS: 431058-53-6
• 化学式: C₁₃H₂₄N₂O₂
• 分子量: 240.346
• InChiKey: VHUSJZPIQCMYND-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R)-3-[1-(tert-butoxycarbonyl-N-methylamino)cyclopropan-1-yl]pyrrolidine 、 difluoroborane {6,7-difluoro-1-[(1R,2S)-2-fluorocyclopropan-1-yl]-1,4-dihydro-8-methoxy-4-oxoquinolin-3-yl}carboxylate 在 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 25.0h， 生成
  参考文献：
  名称：

  Design, synthesis and biological evaluations of novel 7-[3-(1-aminocycloalkyl)pyrrolidin-1-yl]-6-desfluoro-8-methoxyquinolones with potent antibacterial activity against multi-drug resistant Gram-positive bacteria

  摘要：

  A series of novel 6-desfluoro [des-F(6)] and 6-fluoro-1-[(1R,2S)-2-fluorocyclopropan-1-yl]-8-methoxyquinolones bearing 3-(1-aminocycloalkyl)pyrrolidin-1-yl substituents at the C-7 position (1-6) was synthesized to obtain potent drugs for nosocomial infections caused by Gram-positive pathogens. The des-F(6) compounds 4-6 exhibited at least four times more potent activity against representative Gram-positive bacteria than ciprofloxacin or moxifloxacin. Among the derivatives, 7-[(3R)-3-(1-aminocyclopropan-1-yl)pyrrolidin-1-yl] derivative 4, which showed favorable profiles in preliminary toxicological and non-clinical pharmacokinetic studies, exhibited potent antibacterial activity against clinically isolated Gram-positive pathogens that had become resistant to one or more antibiotics. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.026
• 作为产物：
  描述：

  (3R)-3-[1-(tert-butoxycarbonyl-N-methylamino)cyclopropan-1-yl]-1-[(S)-1-phenylethyl]pyrrolidine 在 palladium-carbon 氢气 、 乙醇 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以As a result, 4.38 g (quantitative) of the title compound was obtained in the form of a colorless syrup的产率得到(3R)-3-[1-(tert-butoxycarbonyl-N-methylamino)cyclopropan-1-yl]pyrrolidine
  参考文献：
  名称：

  Dehalogeno compounds

  摘要：

  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。

  公开号：

  US20040063754A1

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。
• DEHALOGENO COMPOUNDS
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP1336611B1

  公开（公告）日：2007-09-05
• 8-CYANOQUINOLONECARBOXYLIC ACID DERIVATIVE
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP1669354B1

  公开（公告）日：2013-03-20
• US7902226B2
  申请人：——

  公开号：US7902226B2

  公开（公告）日：2011-03-08