(S)-1-((R)-2-((N-((4-methoxybenzyl)oxy)formamido)methyl)hexanoyl)-4-methylenepyrrolidine-2-carboxylic acid | 1256162-57-8

• 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: (S)-1-((R)-2-((N-((4-methoxybenzyl)oxy)formamido)methyl)hexanoyl)-4-methylenepyrrolidine-2-carboxylic acid
• CAS: 1256162-57-8
• 化学式: C₂₂H₃₀N₂O₆
• 分子量: 418.49
• InChiKey: OKCBSBODTHUPIF-QUCCMNQESA-N

物化性质

• 沸点：
  613.6±65.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 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：
  96.38
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-1-((R)-2-((N-((4-methoxybenzyl)oxy)formamido)methyl)hexanoyl)-4-methylenepyrrolidine-2-carboxylic acid 在 氯甲酸乙酯 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 (S)-1-((R)-2-((N-hydroxyformamido)methyl)hexanoyl)-4-methylene-N-phenylpyrrolidine-2-carboxamide
  参考文献：
  名称：

  Design, synthesis and antibacterial activity of 3-methylenepyrrolidine formyl hydroxyamino derivatives as novel peptide deformylase inhibitors

  摘要：

  The synthesis and antibacterial activity of 3-methylenepyrrolidine formyl hydroxyamino derivatives are reported. The antibacterial activities of these derivatives were evaluated to discover SAR at P-1' and P-3' positions, and most of these derivatives exhibit better in vitro antibacterial activity than existing drugs against drug-resistant clinical isolates including MRSA, PRSP, and Haemophilus influenzae. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.102
• 作为产物：
  描述：

  4-亚甲基-L-脯氨酸甲酯 在 N-甲基吗啉 、 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 (S)-1-((R)-2-((N-((4-methoxybenzyl)oxy)formamido)methyl)hexanoyl)-4-methylenepyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Design, synthesis and antibacterial activity of 3-methylenepyrrolidine formyl hydroxyamino derivatives as novel peptide deformylase inhibitors

  摘要：

  The synthesis and antibacterial activity of 3-methylenepyrrolidine formyl hydroxyamino derivatives are reported. The antibacterial activities of these derivatives were evaluated to discover SAR at P-1' and P-3' positions, and most of these derivatives exhibit better in vitro antibacterial activity than existing drugs against drug-resistant clinical isolates including MRSA, PRSP, and Haemophilus influenzae. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.102

文献信息

• Synthesis, antibacterial activity, and biological evaluation of formyl hydroxyamino derivatives as novel potent peptide deformylase inhibitors against drug-resistant bacteria
  作者：Shouning Yang、Wei Shi、Dong Xing、Zheng Zhao、Fengping Lv、Liping Yang、Yushe Yang、Wenhao Hu

  DOI：10.1016/j.ejmech.2014.07.106

  日期：2014.10

  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.