| 1189347-71-4

• 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
• CAS: 1189347-71-4
• 化学式: C₆₆H₅₆Cl₂N₁₀O₂₃
• 分子量: 1428.13
• InChiKey: DSVQEIXICIIPPD-DAMZFLOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  101.0
• 可旋转键数：
  6.0
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  517.98
• 氢给体数：
  17.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 在 盐酸 作用下， 反应 2.0h， 以41%的产率得到
  参考文献：
  名称：

  Diazo Transfer−Click Reaction Route to New, Lipophilic Teicoplanin and Ristocetin Aglycon Derivatives with High Antibacterial and Anti-influenza Virus Activity: An Aggregation and Receptor Binding Study

  摘要：

  Semisynthetic, lipophilic ristocetin and teicoplanin derivatives were prepared starting from ristocetin aglycon and teicoplanin psi-aglycon (N-acetyl-D-glucosaminyl aglycoteicoplanin). The terminal amino functions of the aglycons were converted into azido form by triflic azide. Copper catalyzed 1,3-dipolar cycloaddition reaction with lipophilic alkynes resulted in the title compounds. Two of the teicoplanin derivatives showed very good MIC and MBC values against various Gram-positive bacteria, including vanA enterococci. The aggregation and interaction of a n-decyl derivative with bacterial cell wall components Was Studied. One of the lipophilic ristocetin derivatives displayed favorable anti-influenza virus activity.

  DOI：

  10.1021/jm900950d
• 作为产物：
  描述：

  teicoplanin pseudoaglycone 在 triflic azide 、 copper(II) sulfate 、 三乙胺 作用下， 以 吡啶 、 水 为溶剂， 以77%的产率得到
  参考文献：
  名称：

  Diazo Transfer−Click Reaction Route to New, Lipophilic Teicoplanin and Ristocetin Aglycon Derivatives with High Antibacterial and Anti-influenza Virus Activity: An Aggregation and Receptor Binding Study

  摘要：

  Semisynthetic, lipophilic ristocetin and teicoplanin derivatives were prepared starting from ristocetin aglycon and teicoplanin psi-aglycon (N-acetyl-D-glucosaminyl aglycoteicoplanin). The terminal amino functions of the aglycons were converted into azido form by triflic azide. Copper catalyzed 1,3-dipolar cycloaddition reaction with lipophilic alkynes resulted in the title compounds. Two of the teicoplanin derivatives showed very good MIC and MBC values against various Gram-positive bacteria, including vanA enterococci. The aggregation and interaction of a n-decyl derivative with bacterial cell wall components Was Studied. One of the lipophilic ristocetin derivatives displayed favorable anti-influenza virus activity.

  DOI：

  10.1021/jm900950d

文献信息

• Nano-sized clusters of a teicoplanin ψ-aglycon-fullerene conjugate. Synthesis, antibacterial activity and aggregation studies
  作者：Szilvia Tollas、Ilona Bereczki、Attila Sipos、Erzsébet Rőth、Gyula Batta、Lajos Daróczi、Sándor Kéki、Eszter Ostorházi、Ferenc Rozgonyi、Pál Herczegh

  DOI：10.1016/j.ejmech.2012.06.054

  日期：2012.8

  Glycopeptide antibiotic derivative teicoplanin ψ-aglycone has been bound covalently to a fullerenopyrrolidine derivative using azide-alkyne 1,3-dipolar cycloaddition reaction. The aggregation of the antibiotic-fullerene conjugate in aqueous solution has been studied. The conjugate exhibited antibacterial activity against enterococci resistant to teicoplanin.

  糖肽抗生素衍生物替考拉宁ψ-糖苷配基已经通过叠氮化物-炔烃1,3-偶极环加成反应与富勒烯吡咯烷衍生物共价结合。已经研究了抗生素-富勒烯缀合物在水溶液中的聚集。该结合物显示出对替考拉宁耐药的肠球菌的抗菌活性。
• Two Novel Semisynthetic Lipoglycopeptides Active against Staphylococcus aureus Biofilms and Cells in Late Stationary Growth Phase
  作者：Vladimir Vimberg、Leona Zieglerova、Aninda Mazumdar、Zsolt Szűcs、Aniko Borbás、Pál Herczegh、Gabriela Balikova Novotna

  DOI：10.3390/ph14111182

  日期：——

  The increase in antibiotic resistance among Gram-positive bacteria underscores the urgent need to develop new antibiotics. New antibiotics should target actively growing susceptible bacteria that are resistant to clinically accepted antibiotics including bacteria that are not growing or are protected in a biofilm environment. In this paper, we compare the in vitro activities of two new semisynthetic glycopeptide antibiotics, MA79 and ERJ390, with two clinically used glycopeptide antibiotics—vancomycin and teicoplanin. The new antibiotics effectively killed not only exponentially growing cells of Staphylococcus aureus, but also cells in the stationary growth phase and biofilm.

  革兰氏阳性细菌抗生素耐药性的增加强调了开发新抗生素的紧迫性。新的抗生素应该针对活跃生长且对临床接受的抗生素产生抗性的细菌，包括在生物膜环境中不生长或受保护的细菌。在本文中，我们比较了两种新的半合成糖肽类抗生素MA79和ERJ390与两种临床使用的糖肽类抗生素万古霉素和替考普兰在体外活性的差异。新的抗生素不仅有效地杀死了金黄色葡萄球菌的指数生长细胞，还能杀死停滞生长期和生物膜中的细胞。
• Semisynthetic teicoplanin derivatives as new influenza virus binding inhibitors: Synthesis and antiviral studies
  作者：Ilona Bereczki、Máté Kicsák、Laura Dobray、Anikó Borbás、Gyula Batta、Sándor Kéki、Éva Nemes Nikodém、Eszter Ostorházi、Ferenc Rozgonyi、Evelien Vanderlinden、Lieve Naesens、Pál Herczegh

  DOI：10.1016/j.bmcl.2014.06.018

  日期：2014.8

  In order to obtain new, cluster-forming antibiotic compounds, teicoplanin pseudoaglycone derivatives containing two lipophilic n-octyl chains have been synthesized. The compounds proved to be poor anti-bacterials, but, surprisingly, they exhibited potent anti-influenza virus activity against influenza A strains. This antiviral action was related to inhibition of the binding interaction between the virus and the host cell. Related analogs bearing methyl substituents in lieu of the octyl chains, displayed no anti-influenza virus activity. Hence, an interaction between the active, dually n-octylated compounds and the lipid bilayer of the host cell can be postulated, to explain the observed inhibition of influenza virus attachment. (C) 2014 Elsevier Ltd. All rights reserved.