bis(2-pyridylmethyl)glycinamide | 186192-75-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: bis(2-pyridylmethyl)glycinamide
• 英文别名: 2-[Bis(pyridin-2-ylmethyl)amino]acetamide
• CAS: 186192-75-6
• 化学式: C₁₄H₁₆N₄O
• 分子量: 256.307
• InChiKey: LKDDETQVRHUNMP-UHFFFAOYSA-N

物化性质

• 沸点：
  433.5±40.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  72.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  iron(III) chloride hexahydrate 、 bis(2-pyridylmethyl)glycinamide 、 sodium perchlorate 在 NEt₃ 作用下， 以 甲醇 为溶剂， 以20%的产率得到
  参考文献：
  名称：

  双核铁（III）与含酰胺配体配合物催化H 2 O 2氧化环己烷中高活性的化学起源

  摘要：

  两种含氧代桥[Fe 2 OCl 2 L 2 ] [ClO 4 ] 2 ·2H 2 O 1 [L = N，N-双（2-吡啶基甲基）甘氨酰胺]的双核铁（III）配合物的晶体结构和测定了[Fe 2 OCl 2 L 2 ] [ClO 4 ] 2 2（L ＝N- {2- [双（2-（吡啶基甲基）氨基]乙基）吗啉。它们的结构特征与相应的线性双核络合物[Fe 2 OCl 2（tpa）2 ] [ClO 4 ] 2，其中tpa是三（2-吡啶基甲基）胺；配体充当四齿三脚架，Fe–O（酰胺）和平均Fe–N（吗啉）距离分别为2.165（6）和2.45（1）Å。在H 2 O 2存在下，配合物1对环己烷的羟基化具有更高的活性，而其他两种配合物的活性可忽略不计。相反，所有三种配合物都表现出高活性的H 2 O 2分解。这些结果表明，用于环己烷氧化的活性物质可能是铁（ III）-过氧化物加合物（ I），应不同于H 2 O

  DOI：

  10.1039/dt9960004479

文献信息

• [EN] INHIBITORS OF METALLO-BETA-LACTAMASE (MBL) COMPRISING A ZINC CHELATING MOIETY<br/>[FR] INHIBITEURS DE MÉTALLO-BÊTA-LACTAMASE (MBL) COMPRENANT UNE FRACTION DE CHÉLATION DU ZINC
  申请人：UNI I OSLO

  公开号：WO2015049546A1

  公开（公告）日：2015-04-09

  The invention provides compounds according to formula I: A - L - B wherein A represents a lipophilic chelating moiety which is selective for Zn2+ ions; L is a covalent bond or a linker; and B is a vector which is either a moiety capable of interacting with one or more biological structures found in a bacterium (preferably in a bacterial cell wall), for example a penicillin-binding protein such as a metallo-β- lactamase or DD-transferase, or a moiety capable of enhancing transport of the compound across a bacterial cell membrane. Such compounds find use in a method of treating and/or preventing a bacterial infection in a human or non-human mammal. In such a method, the compound of formula I may be administered in combination with (either simultaneously, separately, or sequentially) a β-lactam antibiotic.

  该发明提供了符合以下公式I的化合物：A - L - B，其中A代表选择性对Zn2+离子的亲脂螯合基团；L是共价键或连接物；B是矢量，可以是能与细菌中的一个或多个生物结构相互作用的基团（最好是在细菌细胞壁中找到的），例如金黄色葡萄球菌结合蛋白（例如金属β-内酰胺酶或DD-转移酶），或者是能增强化合物穿过细菌细胞膜的基团。这种化合物可用于治疗和/或预防人类或非人哺乳动物的细菌感染的方法。在这种方法中，公式I的化合物可以与（同时、分开或顺序地）β-内酰胺类抗生素一起给予。
• Inhibitors of Metallo-Beta-Lactamase (MBL) Comprising a Zinc Chelating Moiety
  申请人：UNIVERSITETET I OSLO

  公开号：US20160244431A1

  公开（公告）日：2016-08-25

  Compounds according to formula I are provided: A-L-B wherein A represents a lipophilic chelating moiety which is selective for Zn 2+ ions; L is a covalent bond or a linker; and B is a vector which is either a moiety capable of interacting with one or more biological structures found in a bacterium (preferably in a bacterial cell wall), for example a penicillin-binding protein such as a metallo-β-lactamase or DD-transferase, or a moiety capable of enhancing transport of the compound across a bacterial cell membrane. A method of treating and/or preventing a bacterial infection in a human or non-human mammal employing such compounds are also provided. In such a method, the compound of formula I may be administered in combination with (either simultaneously, separately, or sequentially) a β-lactam antibiotic.

  提供符合公式I的化合物：A-L-B，其中A代表亲脂性螯合基团，该基团选择性地与Zn2+离子结合；L是共价键或连接剂；B是载体，可以是与细菌中的一个或多个生物结构相互作用的基团（优选在细菌细胞壁中），例如与金属β-内酰胺酶或DD转移酶等青霉素结合蛋白相互作用的基团，或者是增强化合物穿过细菌细胞膜的基团。还提供了一种使用这些化合物治疗和/或预防人类或非人哺乳动物细菌感染的方法。在这种方法中，公式I的化合物可以与β-内酰胺类抗生素（同时、分别或顺序）联合使用。
• Inhibitors of metallo-beta-lactamase (MBL) comprising a zinc chelating moiety
  申请人：Universitetet I Oslo

  公开号：US10227327B2

  公开（公告）日：2019-03-12

  Compounds according to formula I are provided: A-L-B wherein A represents a lipophilic chelating moiety which is selective for Zn2+ ions; L is a covalent bond or a linker; and B is a vector which is either a moiety capable of interacting with one or more biological structures found in a bacterium (preferably in a bacterial cell wall), for example a penicillin-binding protein such as a metallo-β-lactamase or DD-transferase, or a moiety capable of enhancing transport of the compound across a bacterial cell membrane. A method of treating and/or preventing a bacterial infection in a human or non-human mammal employing such compounds are also provided. In such a method, the compound of formula I may be administered in combination with (either simultaneously, separately, or sequentially) a β-lactam antibiotic.

  提供了符合式 I 的化合物： A-L-B 其中 A 代表对 Zn2+ 离子具有选择性的亲脂性螯合分子；L 是共价键或连接体；B 是载体，它可以是能够与细菌（最好是细菌细胞壁）中的一种或多种生物结构（例如青霉素结合蛋白，如金属-β-内酰胺酶或 DD-转移酶）相互作用的分子，也可以是能够增强化合物在细菌细胞膜上转运的分子。还提供了一种利用此类化合物治疗和/或预防人类或非人类哺乳动物细菌感染的方法。在这种方法中，式 I 化合物可与β-内酰胺类抗生素（同时、分别或依次）联合给药。
• Models for Amide Ligation in Nonheme Iron Enzymes
  作者：Sanjay K. Mandal、Lawrence Que

  DOI：10.1021/ic970541y

  日期：1997.11.1

  Lipoxygenase and isopenicillin N synthase belong to an emerging class of mononuclear nonheme iron(II) enzymes involved in dioxygen activation.(1) Though these two enzymes catalyze very different reactions, they possess common structural features. Crystal structures(2,3) of these enzymes (Figure 1) show the divalent metal centers to be coordinated to a 2-His-1-carboxylate facial triad(1c) as well as an amide Ligand. These enzymes represent the first examples of amide ligation to iron in biology, a feature not anticipated by prior spectroscopic studies. The amide ligand appears to play a role in catalysis, as indicated by site-directed mutagenesis studies of the two (4,5) To determine the effects of an amide ligand an enzymes. the properties of an iron center, we have synthesized iron complexes of the tetradentate ligand bis(2-pyridylmethyl)glycinamide(BPh4). [Fe-II(BPGm)(0(2)CCH(3))(CH3OH)](BPh4) (1) represents the first example of a complex with a ligand combination that corresponds closely to the coordination environments found for the metal centers in lipoxygenase and isopenicillin N synthase. For comparison, we also report the structures of [Fe-II(TPA)(O2CC(CH3)(3))(CH3OH)](BPh4) (2, TPA = tris(2-pyridylmethyl)amine) and [Fe-2(III)(mu-O)(mu-O2CCH3)-(BPGm)(2)](ClO4)(3) (3) and their properties.
• INHIBITORS OF METALLO-BETA-LACTAMASE (MBL) COMPRISING A ZINC CHELATING MOIETY
  申请人：Universitetet I Oslo

  公开号：EP3052135B1

  公开（公告）日：2018-07-18