On the Synthesis of Phosphonamidate Peptides

Musiol, Hans‐Juergen; Grams, Frank; Rudolph‐Boehner, S.; Moröder, Luis

doi:10.1021/jo00100a007

Cited by 38 publications

(30 citation statements)

References 3 publications

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“…The quinoline scaffold, especially the 8-hydroxyquinoline scaffold can be considered as a privileged structure, [1][2][3] because quinoline-based compounds demonstrate a wide spectrum of biological activities such as anti-inflammatory, cardiovascular, anticonvulsant, antiproliferative, antiprotozoal, antifungal and antibacterial activities. [2,[5][6][7][8][9][10][11][12][13][14][15] They are able to affect specifically many different target structures in cells and are known metal chelators. Thus, their mechanisms of action can be considered as complex, [2,[4][5][6]13,14] which meets the modern definition of socalled multi-target agents.…”

Section: Introductionmentioning

confidence: 99%

8‐Hydroxyquinoline‐2‐Carboxanilides as Antiviral Agents Against Avian Influenza Virus

Kos

Kapustíková

et al. 2019

ChemistrySelect

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Series of thirty‐two mono‐, di‐ and tri‐substituted 8‐hydroxyquinoline‐2‐carboxanilides were prepared by microwave‐assisted synthesis. The compounds were characterized, and their lipophilicity was experimentally determined. Primary in vitro screening of the cytotoxicity of all the synthesized compounds was performed using adenocarcinomic human alveolar basal epithelial cells (A549), and determined nontoxic compounds were then tested for their activity against highly pathogenic H5N1 avian influenza virus. 8‐Hydroxy‐N‐(3,4,5‐trichlorophenyl)quinoline‐2‐carboxamide, N‐(3‐chloro‐2‐fluorophenyl)‐8‐hydroxyquinoline‐2‐carboxamide and N‐(3,4‐dichlorophenyl)‐8‐hydroxyquinoline‐2‐carboxamide demonstrated the highest activity within the investigated series (IC50 = 11.3, 21.2 and 31.2 μM, respectively), while N‐(4‐chloro‐2‐fluorophenyl)‐8‐hydroxyquinoline‐2‐carboxamide expressed the highest cytotoxic effect (CC50 = 31.6 μM). In general, the inhibitory activity of the compounds depends on the position of halogen substituents on the anilide ring and is also affected by the lipophilicity and electron properties of individual substituents of the anilide part of the molecule. The structure‐activity relationships are discussed.

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Section: Introductionmentioning

confidence: 99%

8‐Hydroxyquinoline‐2‐Carboxanilides as Antiviral Agents Against Avian Influenza Virus

Kos

Kapustíková

et al. 2019

ChemistrySelect

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“…Both uronium (TBTU) and phosphonium (PyBOP) reagent‐mediated couplings gave mixtures of two different species, as indicated by MALDI‐MS analysis. For example, in the reaction with allyl amine, the peaks at m / z 1770.31, 1544.42, and 1333.48 could be identified, respectively, as the desired hexa‐, penta‐, and tetra‐acylated allyl amides 6 , whereas the peaks at m / z 1887.12 and 1661.25, respectively, indicated the hexa‐ and penta‐acylated species of the by‐product 8 (in the form of either the phosphate diester or the more stable, rearranged phosphoramidate) (Figure ).…”

Section: Resultsmentioning

confidence: 99%

A Semisynthetic Approach to New Immunoadjuvant Candidates: Site‐Selective Chemical Manipulation of Escherichia coli Monophosphoryl Lipid A

D’Alonzo

Cipolletti

Tarantino

et al. 2016

Chemistry A European J

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A semisynthetic approach to novel lipid A derivatives from Escherichia coli (E. coli) lipid A is reported. This methodology stands as an alternative to common approaches based exclusively on either total synthesis or extraction from bacterial sources. It relies upon the purification of the lipid A fraction from fed-batch fermentation of E. coli, followed by its structural modification through tailored, site-selective chemical reactions. In particular, modification of the lipid pattern and functionalization of the phosphate group as well as of the sole primary hydroxyl group were accomplished, highlighting the unusual reactivity of the molecule. Preliminary investigations of the immunostimulating activity of the new semisynthetic lipid A derivatives show that some of them stand out as promising, new immunoadjuvant candidates.

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“…We know that the BOP reagent is highly efficient for amide formation, carboxylate activation going through an acyloxyphosphonium intermediate to a benzotriazoyl active ester [15]. On the other hand, the BOP reagent is not recommended for phosphonamidate formation [16]. In addition, we have seen that the phosphonic monoester reacts with BOP to form the mixed diester in the presence of an alcohol at high yield [13].…”

Section: Resultsmentioning

confidence: 99%

Recent advances in phosphono- and phosphinopeptide synthesis

Jouin¹,

Coste²,

Galéotti³

et al. 1995

Lett Pept Sci

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Phosphopeptides have been described as protease inhibitors as well as haptens for the preparation of abzymes exhibiting esterase activity. Phosphono-or phosphinopeptides have previously been prepared by solution synthesis, starting from the fully protected phosphoester dipeptide analogue. We have compared the reactivity of phosphonic versus carboxylic acid using BOP-or PyBOP-mediated activation. These reagents have been efficiently used for the preparation of mixed phosphonate diesters in the presence of an alcohol by phosphonic acid activation. We demonstrate their efficiency for solid phase synthesis of phosphonopeptides (or phosphinopeptides) in the presence of an amine by carboxy acid activation, starting from an unprotected phosphodipeptide analogue. In contrast, the efficient BroP-mediated monoesterification of c~-amino-phosphonic acid is not suitable for phosphonopeptide preparation by SPPS.

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On the Synthesis of Phosphonamidate Peptides

Cited by 38 publications

References 3 publications

8‐Hydroxyquinoline‐2‐Carboxanilides as Antiviral Agents Against Avian Influenza Virus

8‐Hydroxyquinoline‐2‐Carboxanilides as Antiviral Agents Against Avian Influenza Virus

A Semisynthetic Approach to New Immunoadjuvant Candidates: Site‐Selective Chemical Manipulation of Escherichia coli Monophosphoryl Lipid A

Recent advances in phosphono- and phosphinopeptide synthesis

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