tert-butyl 3-(tert-butoxycarbonyl)aminomethyl-4-(hydroxyimino)pyrrolidine-1-carboxylate | 175463-36-2

• 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: tert-butyl 3-(tert-butoxycarbonyl)aminomethyl-4-(hydroxyimino)pyrrolidine-1-carboxylate
• 英文别名: Tert-butyl 3-hydroxyimino-4-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidine-1-carboxylate
• CAS: 175463-36-2
• 化学式: C₁₅H₂₇N₃O₅
• 分子量: 329.396
• InChiKey: OINDMHMXFOQNJQ-UHFFFAOYSA-N

物化性质

• 沸点：
  470.1±30.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(tert-butoxycarbonyl)aminomethyl-4-(hydroxyimino)pyrrolidine-1-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 3.58h， 生成 7-[3-(benzylideneamino)methyl-4-(3',4'-methylenedixoybenzyloxyimino)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and in vitro antibacterial activity of gemifloxacin derivatives containing a substituted benzyloxime moiety

  摘要：

  A series of novel gemifloxacin (GMFX) derivatives containing a substituted benzyloxime moiety with remarkable improvement in lipophilicity were synthesized. The target compounds evaluated for their in vitro antibacterial activity against representative strains. Our results reveal that most of the target compounds have considerable potency against all of the tested Gram-positive strains including MRSA and MRSE (MIC: <0.008-8 mu g/mL), although they are generally less active than the references against the Gram-negative strains. In particular, compound 111 (MIC: <0.008-4 mu g/mL) was found to be 8-2048 and 2-128 times more potent than levofloxacin (LVFX) and GMFX against the Gram-positive strains, respectively. Moreover, against MRSA clinical isolates, 111 (MIC90: 1 mu g/mL) is 8-fold more active than GMFX, and 2-fold more active than GMFX and moxifloxacin against MRSE clinical isolates (MIC90: 4 mu g/mL). Crown Copyright (C) 2012 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.010
• 作为产物：
  描述：

  1-Boc-3-氰基-4-吡咯烷酮 在 吡啶 、 5%-palladium/activated carbon 、 盐酸羟胺 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、482.64 kPa 条件下， 反应 17.0h， 生成 tert-butyl 3-(tert-butoxycarbonyl)aminomethyl-4-(hydroxyimino)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis and antibacterial activity of naphthyridone derivatives containing mono/difluoro-methyloxime pyrrolidine scaffolds

  摘要：

  A series of novel naphthyridone derivatives containing mono/difluoro-methyloxime pyrrolidine scaffolds were designed and synthesized. These derivatives were initially evaluated for their in vitro antibacterial activity and compounds 13a1, b1 were chosen for further evaluation their in vivo activity against systemic infections in mice. The results indicate that all of the target compounds have considerable in vitro antibacterial activity. In the in vivo experiments, 13b1 was found to be more effective than the parent drug gemifloxacin against the tested five strains, and especially its activity (ED50:21.27 mg/kg) is 5.2-6.1 times more potent than gemifloxacin and ciprofloxacin against clinically important Gram-negative pathogen Pseudomonas aeruginosa. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.048

文献信息

• Novel quinoline carboxylic acid derivatives having 7-(4-amino-methyl-3-oxime) pyrrolidine substituents and processes for their preparation
  申请人：LG Chemical Limited

  公开号：EP0688772A1

  公开（公告）日：1995-12-27

  The present invention relates to a novel quinolone compound having an excellent antibacterial activity. More specifically, the present invention relates to a novel quinoline(naphthyridine)carboxylic acid derivative represented by the following formula (I), which has an 4-aminomethyl-3-oximepyrrolidine substituent on 7-position of the quinolone nucleus and shows a superior antibacterial activity in contrast to the known quinolone antibactrial agents having a weak activity against gram-positive bacterial strains and also has a broad antibacterial spectrum and a highly improved pharmacokinetic property : wherein R, R₁, R₂, R₃, R₄ and Q are defined as described in the specification.

  本发明涉及一种具有优异抗菌活性的新型喹诺酮化合物。更具体地说，本发明涉及一种由下式（I）表示的新型喹啉（萘啶）羧酸衍生物，该衍生物在喹诺酮核的 7 位上具有 4-氨基甲基-3-氧亚甲基吡咯烷取代基，与对革兰氏阳性细菌菌株活性较弱的已知喹诺酮类抗菌剂相比，显示出更优越的抗菌活性，并且具有广泛的抗菌谱和高度改进的药代动力学特性： 其中 R、R₁、R₂、R₃、R₄ 和 Q 的定义如说明书所述。
• Quinoline carboxylic acid derivatives having 7-(4-amino-methyl-3-oxime) pyrrolidine substituents and processes for their preparation
  申请人：LG Chemical Limited

  公开号：EP0688772B1

  公开（公告）日：1999-05-06
• Synthesis, antimycobacterial and antibacterial activity of l-[(1R,2S)-2-fluorocyclopropyl]naphthyridone derivatives containing an oxime-functionalized pyrrolidine moiety
  作者：Ju Huang、Hongtao Liu、Mingliang Liu、Rui Zhang、Linhu Li、Bin Wang、Minghua Wang、Chunlan Wang、Yu Lu

  DOI：10.1016/j.bmcl.2015.10.027

  日期：2015.11

  A series of novel 1-[(1R,2S)-2-fluorocyclopropyl]naphthyridone derivatives 21-24 containing an oxime-functionalized pyrrolidine moiety were designed, synthesized and evaluated for their biological activity. Our results reveal that compounds 21a, 21e and 21j show considerable activity against MTB H37Rv ATCC 27294 (MICs: <0.25 mu g/mL) and MDR-MTB 6133 (MICs: 0.03-0.054 lg/mL). The target compounds 21-24 are generally poor against the Gram-negative strains, but 21a-j and 22a-c have potent potency (MICs: <0.008-32 mu g/mL) against all of the tested Gram-positive strains including MRSA and MRSE with a few exceptions, and the most active compounds 21d, 21e and 22a-c (MICs: <0.008-32 mu g/mL) were found to be comparable to or better than moxifloxacin, and 2->250 times more potent than ciprofloxacin and levofloxacin. (C) 2015 Elsevier Ltd. All rights reserved.
• US5633262A
  申请人：——

  公开号：US5633262A

  公开（公告）日：1997-05-27
• US5698570A
  申请人：——

  公开号：US5698570A

  公开（公告）日：1997-12-16