tert-butyl 3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-4-[(3,4,5-trimethoxyphenyl)methoxyimino]pyrrolidine-1-carboxylate | 1400792-94-0

• 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-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-4-[(3,4,5-trimethoxyphenyl)methoxyimino]pyrrolidine-1-carboxylate
• CAS: 1400792-94-0
• 化学式: C₂₅H₃₉N₃O₈
• 分子量: 509.6
• InChiKey: TVFPGQSYTGSCST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  117.15
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-4-[(3,4,5-trimethoxyphenyl)methoxyimino]pyrrolidine-1-carboxylate 以 乙醇 、 乙腈 为溶剂， 反应 3.5h， 生成 7-[3-aminomethyl-4-(3',4',5'-trimethxoybenzyloxyimino)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naph-thyridine-3-carboxylic acid dimesylate
  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：

  3,4,5-三甲氧基苄醇 在 三溴化磷 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.58h， 生成 tert-butyl 3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-4-[(3,4,5-trimethoxyphenyl)methoxyimino]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