tert-butyl 3-(1,3-benzodioxol-5-ylmethoxyimino)-4-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidine-1-carboxylate | 175463-46-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: tert-butyl 3-(1,3-benzodioxol-5-ylmethoxyimino)-4-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidine-1-carboxylate
• CAS: 175463-46-4
• 化学式: C₂₃H₃₃N₃O₇
• 分子量: 463.531
• InChiKey: ZAINCBHYIQVHKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 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-(1,3-benzodioxol-5-ylmethoxyimino)-4-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidine-1-carboxylate 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 1-[(1R,2S)-2-fluorocyclopropyl]-6-fluoro-7-[3-aminomethyl-4-(3,4-methylenedioxybenzyloxyimino)pyrrolidine-1-yl]-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid
  参考文献：
  名称：

  Synthesis, antimycobacterial and antibacterial activity of l-[(1R,2S)-2-fluorocyclopropyl]naphthyridone derivatives containing an oxime-functionalized pyrrolidine moiety

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2015.10.027
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 吡啶 、 10% Pd/C 、 盐酸羟胺 、 氢气 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 tert-butyl 3-(1,3-benzodioxol-5-ylmethoxyimino)-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