methyl (S)-1-((R)-2-((N-((4-methoxybenzyl)oxy)formamido)methyl)hexanoyl)-2,5-dihydro-1H-pyrrole-2-carboxylate | 1201518-40-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (S)-1-((R)-2-((N-((4-methoxybenzyl)oxy)formamido)methyl)hexanoyl)-2,5-dihydro-1H-pyrrole-2-carboxylate
• CAS: 1201518-40-2
• 化学式: C₂₂H₃₀N₂O₆
• 分子量: 418.49
• InChiKey: ARYHFMIDRYTESZ-QUCCMNQESA-N

物化性质

• 沸点：
  563.2±60.0 °C(predicted)
• 密度：
  1.183±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  30.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  85.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (S)-1-((R)-2-((N-((4-methoxybenzyl)oxy)formamido)methyl)hexanoyl)-2,5-dihydro-1H-pyrrole-2-carboxylate 在 lithium hydroxide monohydrate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 16.0h， 生成 (S)-1-((R)-2-((N-hydroxyformamido)methyl)hexanoyl)-N-((S)-1-phenylethyl)-2,5-dihydro-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Synthesis, antibacterial activity, and biological evaluation of formyl hydroxyamino derivatives as novel potent peptide deformylase inhibitors against drug-resistant bacteria

  摘要：

  Peptide deformylase (PDF) has been identified as a promising target for novel antibacterial agents. In this study, a series of novel formyl hydroxyamino derivatives were designed and synthesized as PDF inhibitors and their antibacterial activities were evaluated. Among the potent PDF inhibitors (1o, 1q, 1o', 1q', and 1x), in vivo studies showed that compound 1q possesses mild toxicity, a good pharmacokinetic profile and protective effects. The good in vivo efficacy and low toxicity suggest that this class of compounds has potential for development and use in future antibacterial drugs. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.106
• 作为产物：
  描述：

  (R)-2-((4-methoxybenzyloxyamino)methyl)hexanoic acid 在 N-甲基吗啉 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 methyl (S)-1-((R)-2-((N-((4-methoxybenzyl)oxy)formamido)methyl)hexanoyl)-2,5-dihydro-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Synthesis, antibacterial activity, and biological evaluation of formyl hydroxyamino derivatives as novel potent peptide deformylase inhibitors against drug-resistant bacteria

  摘要：

  Peptide deformylase (PDF) has been identified as a promising target for novel antibacterial agents. In this study, a series of novel formyl hydroxyamino derivatives were designed and synthesized as PDF inhibitors and their antibacterial activities were evaluated. Among the potent PDF inhibitors (1o, 1q, 1o', 1q', and 1x), in vivo studies showed that compound 1q possesses mild toxicity, a good pharmacokinetic profile and protective effects. The good in vivo efficacy and low toxicity suggest that this class of compounds has potential for development and use in future antibacterial drugs. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.106

文献信息

• Design, synthesis, and antibacterial activity of 2,5-dihydropyrrole formyl hydroxyamino derivatives as novel peptide deformylase inhibitors
  作者：Wei Shi、Yuejiao Duan、Yu Qian、Ming Li、Liping Yang、Wenhao Hu

  DOI：10.1016/j.bmcl.2010.04.123

  日期：2010.6

  The synthesis and antibacterial activity of 2,5-dihydropyrrole formyl hydroxyamino derivatives are reported. The antibacterial activities of these derivatives were evaluated, and some of these derivatives showed better in vitro antibacterial activity than existing drugs, including penicillin, ciprofloxacin, vancomycin, and linezolid. (C) 2010 Elsevier Ltd. All rights reserved.