(2S)-N-(cyclopentylmethyl)-N-(2-(hydroxyamino)-2-oxo-ethyl)-2-((2-methoxyphenyl)carbamoylamino)-3,3-dimethyl-butanamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (2S)-N-(cyclopentylmethyl)-N-(2-(hydroxyamino)-2-oxo-ethyl)-2-((2-methoxyphenyl)carbamoylamino)-3,3-dimethyl-butanamide
• 英文别名: 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl)carbamoyl)-2,2-dimethylpropyl)-3-(2-methoxyphenyl)urea；(S)-N-(Cyclopentylmethyl)-N-(2-(Hydroxyamino)-2-Oxoethyl)-2-(3-(2-Methoxyphenyl)ureido)-3,3-Dimethylbutanamide；(2S)-N-(cyclopentylmethyl)-N-[2-(hydroxyamino)-2-oxoethyl]-2-[(2-methoxyphenyl)carbamoylamino]-3,3-dimethylbutanamide
• 化学式: C₂₂H₃₄N₄O₅
• 分子量: 434.536
• InChiKey: SGGVRJBZDBEGBH-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  120
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(cyclopentylmethyl-((2S)-2-((2-methoxyphenyl)carbamoylamino)-3,3-dimethyl-butanoyl)amino)acetic acid ethyl ester 在 羟胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以0.022 g的产率得到(2S)-N-(cyclopentylmethyl)-N-(2-(hydroxyamino)-2-oxo-ethyl)-2-((2-methoxyphenyl)carbamoylamino)-3,3-dimethyl-butanamide
  参考文献：
  名称：

  Peptide deformylase inhibitors with retro-amide scaffold: Synthesis and structure–activity relationships

  摘要：

  Peptide deformylase (PDF) is a metalloprotease catalyzing the removal of a formyl group from newly synthesized proteins. Thus inhibition of PDF activity is considered to be one of the most effective antibiotic strategies. Reported herein are the synthesis and structure-activity relationship studies of retro-amide inhibitors based on actinonin, a naturally occurring PDF inhibitor. Analysis of the structure-activity relationships led to the discovery of 7a, which exhibits potent enzyme inhibition and antibacterial activity against Streptococcus pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.088

文献信息

• [EN] DEFORMYLASE INHIBITOR, PROCESS FOR PREPARING THE SAME, AND ANTIBACTERIAL COMPOSITION COMPRISING THE SAME<br/>[FR] INHIBITEUR DE DEFORMYLASE, PROCEDE D'ELABORATION, ET COMPOSITION ANTIBACTERIENNE RENFERMANT CET INHIBITEUR
  申请人：PROMEDITECH INC

  公开号：WO2004087643A1

  公开（公告）日：2004-10-14

  Provided are a novel compound useful for a deformylase inhibitor with excellent antibacterial activity or a pharmaceutically acceptable salt thereof, a process for preparing the same, and an antibacterial composition including the same as an active ingredient. The deformylase inhibitor effectively acts against a broad spectrum of bacteria, including bacteria with resistance to existing antibacterial agents.

  提供了一种新型化合物，用作脱甲酰酶抑制剂，具有出色的抗菌活性，或其药用盐，以及制备该化合物的方法，以及包含该化合物作为活性成分的抗菌组合物。脱甲酰酶抑制剂有效地对抗广谱细菌，包括对现有抗菌剂产生抗性的细菌。
• Peptide deformylase inhibitors with retro-amide scaffold: Synthesis and structure–activity relationships
  作者：Seung Kyu Lee、Kwang Hyun Choi、Sang Jae Lee、Se Won Suh、B. Moon Kim、Bong Jin Lee

  DOI：10.1016/j.bmcl.2010.06.088

  日期：2010.8

  Peptide deformylase (PDF) is a metalloprotease catalyzing the removal of a formyl group from newly synthesized proteins. Thus inhibition of PDF activity is considered to be one of the most effective antibiotic strategies. Reported herein are the synthesis and structure-activity relationship studies of retro-amide inhibitors based on actinonin, a naturally occurring PDF inhibitor. Analysis of the structure-activity relationships led to the discovery of 7a, which exhibits potent enzyme inhibition and antibacterial activity against Streptococcus pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis. (C) 2010 Elsevier Ltd. All rights reserved.