tert-butyl 3-[(2-chloro-3,4-dimethoxyphenyl)methoxyimino]-4-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidine-1-carboxylate | 1400793-01-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl 3-[(2-chloro-3,4-dimethoxyphenyl)methoxyimino]-4-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidine-1-carboxylate
• CAS: 1400793-01-2
• 化学式: C₂₄H₃₆ClN₃O₇
• 分子量: 514.019
• InChiKey: UXXNFPJHVIIIDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  107.92
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-[(2-chloro-3,4-dimethoxyphenyl)methoxyimino]-4-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidine-1-carboxylate 以 乙醇 、 乙腈 为溶剂， 反应 3.5h， 生成 7-[3-(benzylideneamino)methyl-4-(2'-chloro-3',4'-dimethxoybenzyloxyimino)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：

  tert-butyl 3-(tert-butoxycarbonyl)aminomethyl-4-oxopyrrolidine-1-carboxylate 在 吡啶 、 盐酸羟胺 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 tert-butyl 3-[(2-chloro-3,4-dimethoxyphenyl)methoxyimino]-4-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidine-1-carboxylate
  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

文献信息

• Synthesis and in vitro antibacterial activity of gemifloxacin derivatives containing a substituted benzyloxime moiety
  作者：Lianshun Feng、Kai Lv、Mingliang Liu、Shuo Wang、Jing Zhao、Xuefu You、Sujie Li、Jue Cao、Huiyuan Guo

  DOI：10.1016/j.ejmech.2012.07.010

  日期：2012.9

  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.