N-(t-butoxycarbonyloxy)-5-norbornene-endo-2,3-dicarboximide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(t-butoxycarbonyloxy)-5-norbornene-endo-2,3-dicarboximide
• 英文别名: (N-hydroxy-5-norbornene-2,3-dicarboxyl-imido)-tert-butyl-carbonate；N-(tert-butoxycarbonyloxy)-5-norbornene-endo-2,3-dicarboximide；Smtqmxcdeuezrs-ynfqojqrsa-；tert-butyl [(1R,2S,6R,7S)-3,5-dioxo-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl] carbonate
• 化学式: C₁₄H₁₇NO₅
• 分子量: 279.293
• InChiKey: SMTQMXCDEUEZRS-YNFQOJQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(t-butoxycarbonyloxy)-5-norbornene-endo-2,3-dicarboximide 在 N-甲基吗啉 、 三(2-氨基乙基)胺 、 zinc diacetate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 6.25h， 生成 6'-PNZ-2',3,3''-triBoc-sisomicin
  参考文献：
  名称：

  [EN] ANTIBACTERIAL AMINOGLYCOSIDE ANALOGS
  [FR] ANALOGUES D'AMINOGLYCOSIDES ANTIBACTÉRIENS

  摘要：

  结构（I）的化合物具有抗菌活性，包括立体异构体、药用可接受的盐和前药，其中Q1、Q2、Q3、R8和R9如本文所定义。还公开了与制备和使用这些化合物相关的方法，以及包含这些化合物的药物组合物。

  公开号：

  WO2009067692A1
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 N-hydroxy-5-norbomene-2,3-dicarboxylic acid imide 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以89.3%的产率得到N-(t-butoxycarbonyloxy)-5-norbornene-endo-2,3-dicarboximide
  参考文献：
  名称：

  [EN] TREATMENT OF URINARY TRACT INFECTIONS WITH ANTIBACTERIAL AMINOGLYCOSIDE COMPOUNDS
  [FR] TRAITEMENT DES INFECTIONS DES VOIES URINAIRES AVEC DES COMPOSÉS AMINOGLYCOSIDE ANTIBACTÉRIENS

  摘要：

  公开号：

  WO2010132777A3
• 作为试剂：
  描述：

  西索米星 在 甲醇 、 ammonium hydroxide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 N-(t-butoxycarbonyloxy)-5-norbornene-endo-2,3-dicarboximide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 tert-butyl ((2R,3R,4R,5R)-2-(((1S,2S,3R,4S,6R)-3-(((2S,3R)-6-(aminomethyl)-3-((tert-butoxycarbonyl)amino)-3,4-dihydro-2H-pyran-2-yl)oxy)-4-((tert-butoxycarbonyl)amino)-6-((S)-4-((tert-butoxycarbonyl)amino)-2-hydroxybutanamido)-2-hydroxycyclohexyl)oxy)-3,5-dihydroxy-5-methyltetrahydro-2H-pyran-4-yl)(methyl)carbamate
  参考文献：
  名称：

  ANTIBACTERIAL AMINOGLYCOSIDE DERIVATIVES

  摘要：

  本发明涉及一种新的抗菌氨基糖苷衍生物类，包括含有该类化合物的药物组合物，以及其在制备治疗细菌感染相关疾病的药物中的应用。具体公开了一种由公式（II）表示的化合物，其药物可接受的盐和异构体。

  公开号：

  EP3978506A1

文献信息

• 普拉唑米星或其盐的合成方法
  申请人：上海博璞诺科技发展有限公司

  公开号：CN110642907B

  公开（公告）日：2020-11-06

  本发明涉及普拉唑米星或其盐的合成方法，具体地，所述合成方法以化合物6为原料，依次经过交换反应、氨基保护反应、脱除PNZ保护基反应、还原氨化反应、降解反应和脱除氨基保护基反应6个步骤，最终制得了普拉唑米星或其盐，具体步骤详见说明书。本发明的合成方法具有步骤少、反应选择性高、操作简单、物料成本低等优点，非常适合工业化应用。
• Novel conjugates of polysaccharides and uses thereof
  申请人：Lapidot Aviva

  公开号：US20060166867A1

  公开（公告）日：2006-07-27

  Novel conjugates composed of a saccharide-containing moiety (e.g., aminoglycosides) covalently linked to a moiety containing two or more basic amino acid residues (e.g., a polyarginine) and processes of preparing same are disclosed. Further disclosed are pharmaceutical compositions containing these conjugates and uses of these conjugates as antiviral and antibacterial agents.

  揭示了由含有糖类的部分（例如氨基糖苷类）共价连接到含有两个或更多碱性氨基酸残基的部分（例如多精氨酸）组成的新型共轭物，以及制备这些共轭物的方法。进一步揭示了含有这些共轭物的药物组合物以及将这些共轭物用作抗病毒和抗菌剂的用途。
• Conjoint molecules of cephalosporins and aminoglycosides
  作者：Ioannis Grapsas、Stephen A. Lerner、Shahriar Mobashery

  DOI：10.1002/1521-4184(200109)334:8/9<295::aid-ardp295>3.0.co;2-3

  日期：2001.9

  A general synthetic route to conjoint molecules of cephalosporins and aminoglycosides is described. These molecules were designed as potential substrates for bacterial beta -lactamases, enzymes that hydrolyze the beta -lactam bond of cephalosporins. Hydrolysis of the beta -lactam bond was expected to release the Clo-appended aminoglycoside. Since beta -lactamases are sequestered in the periplasmic space of gram-negative bacteria, this sequence of events would liberate aminoglycoside inside such bacteria. It is expected that such local delivery of aminoglycosides would circumvent the inherent toxicity of aminoglycosides that occurs during systemic exposure within the mammalian host.
• N-(tert-Butoxycarbonyloxy)-5-norbornene-endo-2,3-dicarboximide, a Reagent for the Regioselective Introduction of the tert-Butoxycarbonyl (BOC) Protective Group at Unhindered Amines: Application to Amino glycoside Chemistry
  作者：Ioannis Grapsas、Young June Cho、Shahriar Mobashery

  DOI：10.1021/jo00086a055

  日期：1994.4
• Loss of individual electrostatic interactions between aminoglycoside antibiotics and resistance enzymes as an effective means to overcoming bacterial drug resistance
  作者：Juliatiek Roestamadji、Ioannis Grapsas、Shahriar Mobashery

  DOI：10.1021/ja00150a004

  日期：1995.11

  Aminoglycoside-modifying enzymes modify the structures of aminoglycoside antibiotics, rendering them ineffective, a process which confers resistance to the antibiotic. Electrostatic interactions (ion pairing and hydrogen bonding) are believed to be significant for both substrate recognition and catalysis by these enzymes. Regiospecific syntheses of seven distinct deaminated analogues of neamine and kanamycin A, two aminoglycoside antibiotics, are described. Each of these compounds would have impaired interaction with a different subsite of the enzyme active sites. All seven molecules were shown to be exceedingly poor substrates for two aminoglycoside-modifying enzymes, aminoglycoside 3'-phosphotransferases types Ia and IIa. The energetic contribution of interactions of the active-site functions with each of these amines on stabilization of the transition-state species has been evaluated to be in the range of 6-11 kcal/mol, the largest energy contribution recorded in the literature for such interactions. The biological activities of these analogues were the same against the resistant organisms harboring aminoglycoside 3'-phosphotransferases types Ia and IIa as those against the background strain without the resistant enzymes. Thus, these compounds are virtually unmodified by those enzymes in vivo. The principles described here should be of general interest for circumvention of resistance to other antibiotics, by redesigning the electrostatic interactions with their corresponding resistance enzymes.

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