BB 3497 | 235784-88-0

• 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 3497
• 英文别名: BB-3497；2R-[(formyl-hydroxy-amino)-methyl]-hexanoic acid (1S-dimethylcarbamoyl-2,2-dimethyl-propyl)-amide；2-[(Formyl-hydroxy-amino)-methyl]-hexanoic acid (1-dimethylcarbamoyl-2,2-dimethyl-propyl)-amide；(2R)-N-[(2S)-1-(dimethylamino)-3,3-dimethyl-1-oxobutan-2-yl]-2-[[formyl(hydroxy)amino]methyl]hexanamide
• CAS: 235784-88-0
• 化学式: C₁₆H₃₁N₃O₄
• 分子量: 329.44
• InChiKey: AVDLWYHBABSSHC-CHWSQXEVSA-N

物化性质

• 密度：
  1.077±0.06 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  calcium chloride 、 BB 3497 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 24.0h， 生成 2R-[(formyl-hydroxy-amino)-methyl]-hexanoic acid (1S-dimethylcarbamoyl-2,2-dimethyl-propyl)-amide calcium salt
  参考文献：
  名称：

  [EN] CRYSTALLINE N-FORMYL HYDROXYLAMINE COMPOUNDS
  [FR] COMPOSES N-FORMYL-HYDROXYLAMINE CRISTALLINS

  摘要：

  某些N-甲酰羟胺化合物，例如N-[1-氧代-2-烷基-3-(N-羟甲酰胺基)-丙基]-(羰基氨基-芳基或-杂环芳基)-氮杂环4-7烷或硫杂环4-7烷或咪唑氮杂环4-7烷，在治疗细菌感染方面是有用的。公开了该式(I)化合物的晶体盐，其中M是一价或二价金属；a为1/2或1。

  公开号：

  WO2004087133A1
• 作为产物：
  描述：

  (2R)-2-({[(phenylmethyl)oxy]amino}methyl)hexanoic acid 在 palladium on activated charcoal N-羟基-7-氮杂苯并三氮唑 、 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 BB 3497
  参考文献：
  名称：

  Asymmetric synthesis of bb-3497—A potent peptide deformylase inhibitor

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(01)00509-1

文献信息

• Peptide deformylase inhibitors as novel antibiotics
  申请人：Pei Dehua

  公开号：US20070259812A1

  公开（公告）日：2007-11-08

  A macrocyclic peptide deformylase (PDF) inhibitor comprising a peptide or peptide mimetic having three residues, P1′, P2′, and P3′, wherein P2′ connects P1′ and P3′, wherein P1′ and P3′ each have a side chain, and wherein the side chains on P1′ and P3′ are crosslinked to form the macrocyclic PDF inhibitor. The side chains of P1′ and P3′ interact with the PDF active site, and preferably, P2′ has a side chain that interacts with a solvent. Also provided are methods of inhibiting the growth of a bacterium, the methods comprising contacting the bacterium with an anti-bacterial effective amount of the inventive macrocyclic PDF inhibitor. Additionally, a method of treating a bacterial infection in a subject comprising administering an effective amount of a macrocyclic PDF inhibitor to a subject in need of treatment. Additionally, methods of preparing macrocyclic PDF inhibitors comprising a) choosing an acyclic base molecule, having at least some PDF inhibitory activity, the acyclic base molecule having a first residue having a first side chain that interacts with the PDF active site and a second residue having a second that interacts with the PDF active site; and b) crosslinking the first side chain and the second side chain to form a macrocyclic PDF inhibitor.

  一种环状肽变形酶（PDF）抑制剂，包括一个具有三个残基P1'、P2'和P3'的肽或肽类似物，其中P2'连接P1'和P3'，P1'和P3'各具有一个侧链，P1'和P3'的侧链交叉连接形成环状PDF抑制剂。P1'和P3'的侧链与PDF活性位点相互作用，优选地，P2'具有与溶剂相互作用的侧链。还提供了抑制细菌生长的方法，该方法包括使用本发明的环状PDF抑制剂与细菌接触以达到抗菌的有效量。此外，还提供了一种治疗受感染者细菌感染的方法，包括向需要治疗的受感染者施用有效量的环状PDF抑制剂。此外，还提供了制备环状PDF抑制剂的方法，包括：a）选择具有至少一定程度PDF抑制活性的非环状基分子，其中该非环状基分子具有第一个残基，该第一个残基具有与PDF活性位点相互作用的第一个侧链，以及第二个残基，该第二个残基具有与PDF活性位点相互作用的第二个侧链；和b）交叉连接第一个侧链和第二个侧链以形成环状PDF抑制剂。
• PEPTIDE DEFORMYLASE INHIBITORS AS NOVEL ANTIBIOTICS
  申请人：Pei Dehua

  公开号：US20090203631A1

  公开（公告）日：2009-08-13

  A macrocyclic peptide deformylase (PDF) inhibitor comprising a peptide or peptide mimetic having three residues, P 1′, P 2′, and P 3′, wherein P 2′ connects P 1′ and P 3′, wherein P 1′ and P 3′ each have a side chain, and wherein the side chains on P 1′ and P 3′ are crosslinked to form the macrocyclic PDF inhibitor. The side chains of P 1′ and P 3′ interact with the PDF active site, and preferably, P 2′ has a side chain that interacts with a solvent. Also provided are methods of inhibiting the growth of a bacterium, the methods comprising contacting the bacterium with an anti-bacterial effective amount of the inventive macrocyclic PDF inhibitor. Additionally, a method of treating a bacterial infection in a subject comprising administering an effective amount of a macrocyclic PDF inhibitor to a subject in need of treatment. Additionally, methods of preparing macrocyclic PDF inhibitors comprising a) choosing an acyclic base molecule, having at least some PDF inhibitory activity, the acyclic base molecule having a first residue having a first side chain that interacts with the PDF active site and a second residue having a second that interacts with the PDF active site; and b) crosslinking the first side chain and the second side chain to form a macrocyclic PDF inhibitor.

  一种宏环肽脱甲基酶（PDF）抑制剂，包括一个具有三个残基P1'、P2'和P3'的肽或肽类似物，其中P2'连接P1'和P3'，P1'和P3'各自具有一个侧链，并且P1'和P3'的侧链交叉连接以形成宏环PDF抑制剂。P1'和P3'的侧链与PDF活性位点相互作用，最好的情况是，P2'具有与溶剂相互作用的侧链。还提供了一种抑制细菌生长的方法，该方法包括将具有抗菌有效量的创新宏环PDF抑制剂与细菌接触。此外，还提供了一种治疗受感染者的细菌感染的方法，包括向需要治疗的受试者施用有效量的宏环PDF抑制剂。此外，还提供了制备宏环PDF抑制剂的方法，包括a）选择一个具有至少一定程度的PDF抑制活性的非环状基分子，该非环状基分子具有一个具有与PDF活性位点相互作用的第一侧链的第一残基和一个具有与PDF活性位点相互作用的第二侧链的第二残基；并且b）交叉连接第一侧链和第二侧链以形成宏环PDF抑制剂。
• Crystalline n-formyl hydroxylamine compounds
  申请人：Slade Joel

  公开号：US20070135353A1

  公开（公告）日：2007-06-14

  Certain N-formyl hydroxylamine compounds, such as N-[1-oxo-2-alkyl-3-(N-hydroxyformamido)-propyl]-(carbonylamino-aryl or -heteroaryl)-azacyclo 4-7 alkanes or thiazacyclo 4-7 alkanes or imidazacyclo 4-7 alkanes are useful in the treatment of bacterial infections. Disclosed are crystalline salts of such compounds of formula (I), wherein M is a mono- or di-valent metal; a is ½ or 1.
• US7208595B2
  申请人：——

  公开号：US7208595B2

  公开（公告）日：2007-04-24
• US7323448B2
  申请人：——

  公开号：US7323448B2

  公开（公告）日：2008-01-29