N-hydroxy-3-phenyl-N'-(2-phenylethyl)propanimidamide

• 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: N-hydroxy-3-phenyl-N'-(2-phenylethyl)propanimidamide
• 化学式: C₁₇H₂₀N₂O
• 分子量: 268.359
• InChiKey: ODEVFGSNLSJGKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  44.6
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-phenethyl-3-phenylpropanethioamide 在 silver tetrafluoroborate 、 羟胺 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以87%的产率得到N-hydroxy-3-phenyl-N'-(2-phenylethyl)propanimidamide
  参考文献：
  名称：

  GLYCOPEPTIDE ANTIBIOTIC ANALOGS EFFECTIVE AGAINST VANCOMYCIN-RESISTANT BACTERIAL STRAINS

  摘要：

  公开号：

  EP2739289B1

文献信息

• [EN] GLYCOPEPTIDE ANTIBIOTIC ANALOGS EFFECTIVE AGAINST VANCOMYCIN-RESISTANT BACTERIAL STRAINS<br/>[FR] ANALOGUES D'ANTIBIOTIQUES GLYCOPEPTIDIQUES EFFICACES CONTRE DES SOUCHES BACTÉRIENNES RÉSISTANTES À LA VANCOMYCINE
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2013022763A1

  公开（公告）日：2013-02-14

  The invention is directed to glycopeptide antibiotics and their aglycones that are engineered to overcome bacterial resistance by replacement of a single, specific peptide carboxamide group in the core peptide of the glycopeptide antibiotic with an amidine group. The amidine pseudopeptide analog of the glycopeptide is effective in killing vancomycin-resistant bacteria at therapeutically achievable concentrations in a patient. For example, a [ψ[C(=NH)NH]Tpg4]-vancomycin aglycon designed to exhibit the dual binding to D-Ala-D-Ala and D-Ala-D-Lac needed to reinstate activity against vancomycin-resistant bacteria has been shown to overcome a common mode of bacterial resistance to the "last resort" antibiotics of the glycopeptide class. The pseudopeptide amidine analogs can be prepared from corresponding pseudopeptide thioamide analogs, which can be prepared synthetically, semi-synthetically, or biosynthetically.

  本发明涉及糖肽抗生素及其无糖基物，通过将糖肽抗生素的核心肽中的单一、特定的肽羧酰胺基团替换为氨基亚胺基团，以克服细菌抗药性的工程化。糖肽的氨基亚胺伪肽类似物在患者体内的治疗可达浓度下有效地杀灭万古霉素耐药菌。例如，设计用于表现对D-Ala-D-Ala和D-Ala-D-Lac双重结合所需的[ψ[C(=NH)NH]Tpg4]-万古霉素无糖基物已被证明能克服糖肽类“最后一道防线”抗生素常见的细菌耐药机制。伪肽氨基亚胺类似物可以从相应的伪肽硫酰胺类似物中制备，这些类似物可以通过合成、半合成或生物合成制备。
• Silver(I)-Promoted Conversion of Thioamides to Amidines: Divergent Synthesis of a Key Series of Vancomycin Aglycon Residue 4 Amidines That Clarify Binding Behavior to Model Ligands
  作者：Akinori Okano、Robert C. James、Joshua G. Pierce、Jian Xie、Dale L. Boger

  DOI：10.1021/ja302808p

  日期：2012.5.30

  Development of a general Ag(I)-promoted reaction for the conversion of thioamides to amidines is disclosed. This reaction was employed to prepare a key series of vancomycin aglycon residue 4 substituted amidines that were used to clarify their interaction with model ligands of peptidoglycan precursors and explore their resulting impact on antimicrobial properties.
• US9879049B2
  申请人：——

  公开号：US9879049B2

  公开（公告）日：2018-01-30
• GLYCOPEPTIDE ANTIBIOTIC ANALOGS EFFECTIVE AGAINST VANCOMYCIN-RESISTANT BACTERIAL STRAINS
  申请人：The Scripps Research Institute

  公开号：EP2739289B1

  公开（公告）日：2020-05-06