(S,Z)-N-benzylidene-4-(benzyloxycarbonylamino)-4-carboxybutan-1-amine oxide | 250215-09-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S,Z)-N-benzylidene-4-(benzyloxycarbonylamino)-4-carboxybutan-1-amine oxide
• 英文别名: N-[(4S)-4-carboxy-4-(phenylmethoxycarbonylamino)butyl]-1-phenylmethanimine oxide
• CAS: 250215-09-9；444154-85-2
• 化学式: C₂₀H₂₂N₂O₅
• 分子量: 370.405
• InChiKey: JSDVOGKKRRBQQG-GFHXCNCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S,Z)-N-benzylidene-4-(benzyloxycarbonylamino)-4-carboxybutan-1-amine oxide 在 盐酸 、 potassium acetate 、 potassium hydrogencarbonate 、 溶剂黄146 、 三氟乙酸 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 4.75h， 生成 N²-benzyloxycarbonyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithine
  参考文献：
  名称：

  Practical Synthesis of Hydroxamate-Derived Siderophore Components by an Indirect Oxidation Method and Syntheses of a DIG−Siderophore Conjugate and a Biotin−Siderophore Conjugate

  摘要：

  A practical large-scale synthesis of hydroxamate-derived siderophore components (30 and 40) that utilizes an efficient indirect oxidation method is described and applied to the syntheses of nonradioactive labeled siderophores. Oxidation of imines derived from L-ornithine (17) and its tripeptide (19) afforded oxaziridines that were isomerized to stable-nitrones (16 and 18). Acid-catalyzed hydrolysis of nitrones provided hydroxylamines that were converted to the desired hydroxamic acids (30 and 40) suitable for constructing siderophore-drug conjugates (2). The entire synthetic sequence required no chromatographic separation. DIG- and biotin-labeled ferrichrome analogues designed to detect and isolate ferrichrome receptors in various microbes were also synthesized.

  DOI：

  10.1021/jo990769y
• 作为产物：
  描述：

  Cbz-L-鸟氨酸 在 氢氧化钾 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (S,Z)-N-benzylidene-4-(benzyloxycarbonylamino)-4-carboxybutan-1-amine oxide
  参考文献：
  名称：

  Practical Synthesis of Hydroxamate-Derived Siderophore Components by an Indirect Oxidation Method and Syntheses of a DIG−Siderophore Conjugate and a Biotin−Siderophore Conjugate

  摘要：

  A practical large-scale synthesis of hydroxamate-derived siderophore components (30 and 40) that utilizes an efficient indirect oxidation method is described and applied to the syntheses of nonradioactive labeled siderophores. Oxidation of imines derived from L-ornithine (17) and its tripeptide (19) afforded oxaziridines that were isomerized to stable-nitrones (16 and 18). Acid-catalyzed hydrolysis of nitrones provided hydroxylamines that were converted to the desired hydroxamic acids (30 and 40) suitable for constructing siderophore-drug conjugates (2). The entire synthetic sequence required no chromatographic separation. DIG- and biotin-labeled ferrichrome analogues designed to detect and isolate ferrichrome receptors in various microbes were also synthesized.

  DOI：

  10.1021/jo990769y

文献信息

• ANTIBACTERIAL AGENTS
  申请人：Moser Heinz E.

  公开号：US20100190766A1

  公开（公告）日：2010-07-29

  Antibacterial compounds of formula (I) are provided: as well as stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of such compounds.

  提供化学式(I)的抗菌化合物：以及其立体异构体，药学上可接受的盐，酯和前药；包含这些化合物的制药组合物；通过给予这些化合物的途径治疗细菌感染的方法；以及制备这些化合物的过程。
• Antibacterial agents
  申请人：Achaogen, Inc.

  公开号：EP2662353A2

  公开（公告）日：2013-11-13

  Antibacterial compounds of formula (I) are provided, as well as stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of such compounds.

  提供了式 (I) 的抗菌化合物及其立体异构体、药学上可接受的盐、酯和原药；包含此类化合物的药物组合物；通过服用此类化合物治疗细菌感染的方法；以及制备此类化合物的工艺。
• BACTERIAL SIDEROPHORE GRAMIBACTIN
  申请人：Leibniz-Institut für Naturstoff-Forschung und Infektionsbiologi - Hans-Knöll-Institut

  公开号：US20210054028A1

  公开（公告）日：2021-02-25

  A peptide siderophore, includes one or more N-nitroso-hydroxylamine ligands. The peptide siderophore can include two side chains, each with a N-nitroso-hydroxylamine ligand, and a further side chain with one or more hydroxy carboxylic acid, hydroxamate, catecholate and/or salicylate ligands. The siderophore can be cyclic. A bacterial cell can express the peptide siderophore, and a composition can include the peptide siderophore, for example in the form of its corresponding iron-complex or bacteria. A method for promoting plant growth, promoting root growth or development, improving stress tolerance in a plant, increasing crop yields of a plant, delivering nitric oxide (NO) to a plant, and/or enhancing chlorophyll production in a plant includes administering the peptide siderophore, bacteria expressing the peptide siderophore or a composition including the peptide siderophore to the plant.
• [EN] ANTIBACTERIAL AGENTS<br/>[FR] AGENTS ANTIBACTÉRIENS
  申请人：ACHAOGEN INC

  公开号：WO2008154642A2

  公开（公告）日：2008-12-18

  [EN] Antibacterial compounds of formula (I) are provided, as well as stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of such compounds.
  [FR] L'invention propose des composés antibactériens de formule (I), ainsi que des stéréoisomères, des sels pharmaceutiques acceptables, des esters et des promédicaments de ceux-ci ; des compositions pharmaceutiques comportant de tels composés ; des procédés de traitement d'infections bactériennes par l'administration de tels composés ; et des procédés pour la préparation de tels composés.
• Practical Synthesis of Hydroxamate-Derived Siderophore Components by an Indirect Oxidation Method and Syntheses of a DIG−Siderophore Conjugate and a Biotin−Siderophore Conjugate
  作者：Yun-Ming Lin、Marvin J. Miller

  DOI：10.1021/jo990769y

  日期：1999.10.1

  A practical large-scale synthesis of hydroxamate-derived siderophore components (30 and 40) that utilizes an efficient indirect oxidation method is described and applied to the syntheses of nonradioactive labeled siderophores. Oxidation of imines derived from L-ornithine (17) and its tripeptide (19) afforded oxaziridines that were isomerized to stable-nitrones (16 and 18). Acid-catalyzed hydrolysis of nitrones provided hydroxylamines that were converted to the desired hydroxamic acids (30 and 40) suitable for constructing siderophore-drug conjugates (2). The entire synthetic sequence required no chromatographic separation. DIG- and biotin-labeled ferrichrome analogues designed to detect and isolate ferrichrome receptors in various microbes were also synthesized.