(2R)-2-[formyl(phenylmethoxy)amino]methylhexanoic acid dicyclohexylamine

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R)-2-[formyl(phenylmethoxy)amino]methylhexanoic acid dicyclohexylamine
• 英文别名: (2R)-2-[[formyl(phenylmethoxy)amino]methyl]-hexanoic acid dicyclohexylamine salt；N-cyclohexylcyclohexanamine;(2R)-2-[[formyl(phenylmethoxy)amino]methyl]hexanoic acid
• 化学式: C₁₂H₂₃N*C₁₅H₂₁NO₄
• 分子量: 460.657
• InChiKey: IKSJKFRKPKLPRD-PFEQFJNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.71
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R)-2-[formyl(phenylmethoxy)amino]methylhexanoic acid dicyclohexylamine 在 palladium on activated charcoal 苯酐 、 双氧水 、 甲酸铵 、 尿素 作用下， 反应 4.0h， 生成 LBM-415
  参考文献：
  名称：

  β-Amino Amides from β-Lactams: Application to the Formal Synthesis of a Peptide-Deformylase Inhibitor

  摘要：

  描述了一种简单且实用的肽去甲酰化酶抑制剂1的合成方法，该方法使用酸催化的氨基醇解反应，将β-内酰胺12与哌啶6作为关键转化。此外，还报告了将β-羟酸转化为β-内酰胺的简化条件。

  DOI：

  10.1055/s-2006-951499
• 作为产物：
  描述：

  (2R)-2-({[(phenylmethyl)oxy]amino}methyl)hexanoic acid 以 正庚烷 、 乙酸酐 为溶剂， 生成 (2R)-2-[formyl(phenylmethoxy)amino]methylhexanoic acid dicyclohexylamine
  参考文献：
  名称：

  Synthesis and in vitro antibacterial activity of oxazolidine LBM-415 analogs as peptide deformylase inhibitors

  摘要：

  The drug resistant bacteria pose a severe threat to human health. The increasing resistance of those pathogens to traditional antibacterial therapy renders the identification of new antibacterial agents with novel antibacterial mechanisms an urgent need. In this study, a series of (2S)-N-substituted-1-[(formyhydroxyamino) methyl]-1-oxohexyl]-2-oxazolidinecarboxamides were designed, synthesized and evaluated for in vitro antibacterial activity. Most of these compounds displayed good activities against Gram-positive organisms comparable to reference agent LBM-415. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.097

文献信息

• [EN] PROCESS FOR PREPARING INTERMEDIATES USEFUL TO PREPARE CERTAIN ANTIBACTERIAL N-FORMYL HYDROXYLAMINES<br/>[FR] PROCEDE DE PREPARATION D'INTERMEDIAIRES SERVANT A PREPARER CERTAINES N-FORMYLE HYDROXYLAMINES ANTIBACTERIENNES
  申请人：NOVARTIS AG

  公开号：WO2005000835A1

  公开（公告）日：2005-01-06

  The present invention is directed to a process for preparing intermediates that are useful to prepare certain antibacterial N-formyl hydroxylamine compounds which are peptide deformylase inhibitors.

  本发明涉及一种用于制备中间体的方法，这些中间体可用于制备特定的抗菌N-甲酰羟胺化合物，这些化合物是肽去甲酰化酶抑制剂。
• A Practical Enantioselective Synthesis of a Novel Peptide Deformylase Inhibitor
  作者：Joel Slade、David Parker、Michael Girgis、Martin Mueller、James Vivelo、Hui Liu、Joginder Bajwa、Guang-Pei Chen、Joseph Carosi、Paul Lee、Apurva Chaudhary、Dana Wambser、Kapa Prasad、Kathryn Bracken、Karl Dean、Helmut Boehnke、Oljan Repič、Thomas J. Blacklock

  DOI：10.1021/op050165y

  日期：2006.1.1

  A practical synthesis of the peptide deformylase inhibitor LBM415, (2S)-N-(5-fluoro-1-oxido-2-pyridinyl)-1-[(2R)-2-[(formylhydroxyamino)methyl]-1-oxohexyl]-2-pyrrolidinecarboxamide, magnesium salt 11, is described. The key chiral intermediate, (2S)-N-(5-fluoro-2-pyridinyl)-1-[(2R)-2-[[formyl(phenylmethoxy)amino]methyl]-1-oxohexyl]-2-pyrrolidinecarboxamide 8, was made by coupling the corresponding amino

  肽去甲酰基酶抑制剂LBM415，（2 S）-N-（5-氟-1-氧化-2-吡啶基）-1-[（2 R）-2-[（甲酰基羟氨基）甲基] -1-的实用合成描述了氧己基] -2-吡咯烷甲酰胺，镁盐11。关键的手性中间体，（2 S）-N-（5-氟-2-吡啶基）-1-[（2 R）-2-[[甲酰基（苯基甲氧基）氨基]甲基] -1-氧己基] -2-吡咯烷甲酰胺8，按与相应的氨基酸偶联制成7与甲酰胺25从制备升-脯氨酸和2-氨基-5-氟吡啶。吡啶氮氧化后，对苄基进行选择性氢解得到原料药的游离酸，将其用氯化镁原位转化为镁盐。得到的产物的总产率为16％，ee＞ 99％。
• Process for preparing intermediates useful to prepare certain antibacterial n-formyl hydroxylamines
  申请人：Slade Joel

  公开号：US20070060753A1

  公开（公告）日：2007-03-15

  The present invention is directed to a process for preparing intermediates that are useful to prepare certain antibacterial N-formyl hydroxylamine compounds which are peptide deformylase inhibitors.
• PROCESS FOR PREPARING INTERMEDIATES USEFUL TO PREPARE CERTAIN ANTIBACTERIAL N-FORMYL HYDROXYLAMINES
  申请人：SLADE Joel

  公开号：US20090118515A1

  公开（公告）日：2009-05-07

  The present invention is directed to a process for preparing intermediates that are useful to prepare certain antibacterial N-formyl hydroxylamine compounds which are peptide deformylase inhibitors.
• β-Amino Amides from β-Lactams: Application to the Formal Synthesis of a Peptide-Deformylase Inhibitor
  作者：Kapa Prasad、Xinglong Jiang、Mahavir Prashad、Joel Slade、Oljan Repič、Thomas Blacklock

  DOI：10.1055/s-2006-951499

  日期：2006.11

  A facile and a practical synthesis of peptide-deformylase inhibitor 1 is described using an acid-catalyzed aminolysis of β-lactam 12 with pyrrolidine 6 as the key transformation. In addition, simplified conditions for the conversion of a β-hydroxy acid to a β-lactam are reported.

  描述了一种简单且实用的肽去甲酰化酶抑制剂1的合成方法，该方法使用酸催化的氨基醇解反应，将β-内酰胺12与哌啶6作为关键转化。此外，还报告了将β-羟酸转化为β-内酰胺的简化条件。