BB-3554

• 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: BB-3554
• 英文别名: For-N(OH)bAla(2S-Bu)-Gly(tBu)-NMe2；(2S)-N-[(2S)-1-(dimethylamino)-3,3-dimethyl-1-oxobutan-2-yl]-2-[[formyl(hydroxy)amino]methyl]hexanamide
• 化学式: C₁₆H₃₁N₃O₄
• 分子量: 329.44
• InChiKey: AVDLWYHBABSSHC-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  90
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  正己酸乙酯 在 palladium on activated charcoal sodium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 氢气 、 sodium ethanolate 、 sodium acetate 、 sodium cyanoborohydride 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 BB-3554
  参考文献：
  名称：

  Structure–activity relationships of the peptide deformylase inhibitor BB-3497: modification of the methylene spacer and the P1′ side chain

  摘要：

  Structural modifications to the peptide deformylase inhibitor BB-3497 are described. In this paper, we describe the initial SAR around this lead for modifications to the methylene spacer and the P1' side chain. Enzyme inhibition and antibacterial activity data revealed that the optimum distance between the N-formyl hydroxylamine metal binding group and the P1' side chain is one unsubstituted methylene unit. Additionally, lipophilic P1' side chains that closely mimic the methionine residue in the substrate provided compounds with the best microbiological profile. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00532-8

文献信息

• Asymmetric synthesis of bb-3497—A potent peptide deformylase inhibitor
  作者：Lisa M Pratt、R.Paul Beckett、Stephen J Davies、Steven B Launchbury、Andrew Miller、Zoe M Spavold、Richard S Todd、Mark Whittaker

  DOI：10.1016/s0960-894x(01)00509-1

  日期：2001.10

  By screening a library of metalloenzyme inhibitors, the N-formyl-hydroxylamine derivative BB-3497 was identified as a potent inhibitor of Escherichia coli peptide deformylase with antibacterial activity both in vitro and in vivo. The homochiral synthesis of BB-3497, involving a novel asymmetric Michael addition reaction is described. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Structure–activity relationships of the peptide deformylase inhibitor BB-3497: modification of the methylene spacer and the P1′ side chain
  作者：Stephen J. Davies、Andrew P. Ayscough、R.Paul Beckett、Ryan A. Bragg、John M. Clements、Sheila Doel、Christine Grew、Steven B. Launchbury、Gemma M. Perkins、Lisa M. Pratt、Helen K. Smith、Zoë M. Spavold、S.Wayne Thomas、Richard S. Todd、Mark Whittaker

  DOI：10.1016/s0960-894x(03)00532-8

  日期：2003.8

  Structural modifications to the peptide deformylase inhibitor BB-3497 are described. In this paper, we describe the initial SAR around this lead for modifications to the methylene spacer and the P1' side chain. Enzyme inhibition and antibacterial activity data revealed that the optimum distance between the N-formyl hydroxylamine metal binding group and the P1' side chain is one unsubstituted methylene unit. Additionally, lipophilic P1' side chains that closely mimic the methionine residue in the substrate provided compounds with the best microbiological profile. (C) 2003 Elsevier Ltd. All rights reserved.