scholarly journals Synthetic Methods of Phosphonopeptides

Molecules ◽  
2020 ◽  
Vol 25 (24) ◽  
pp. 5894
Author(s):  
Jiaxi Xu
Keyword(s):  
Enzyme Inhibitors ◽  
Condensation Reaction ◽  
Catalytic Antibodies ◽  
Synthetic Methods ◽  
Coupling Reagents ◽  
Efficient Strategy ◽  
Peptide Esters ◽  
Aminoalkylphosphonic Acid

Phosphonopeptides are phosphorus analogues of peptides and have been widely applied as enzyme inhibitors and antigens to induce catalytic antibodies. Phosphonopeptides generally contain one aminoalkylphosphonic acid residue and include phosphonopeptides with C-terminal aminoalkylphosphonic acids and phosphonopeptides with a phosphonamidate bond. The phosphonamidate bond in the phosphonopeptides is generally formed via phosphonylation with phosphonochloridates, condensation with coupling reagents and enzymes, and phosphinylation followed by oxidation. Pseudo four-component condensation reaction of amides, aldehydes, alkyl dichlorophosphites, and amino/peptide esters is an alternative, convergent, and efficient strategy for synthesis of phosphonopeptides through simultaneous construction of aminoalkylphosphonic acids and formation of the phosphonamidate bond. This review focuses on the synthetic methods of phosphonopeptides containing a phosphonamidate bond.

Double Ring-Closing Approach for the Synthesis of 2,3,6,7-Substituted Anthracene Derivatives

2020 ◽  
Author(s):  
Birgit Meindl ◽  
Katharina Pfennigbauer ◽  
Berthold Stöger ◽  
Martin Heeney ◽  
Florian Glöcklhofer
Keyword(s):  
Wittig Reaction ◽  
Condensation Reaction ◽  
Synthetic Methods ◽  
Anthracene Derivative ◽  
Double Ring ◽  
Mild Conditions ◽  
Wide Range ◽  
Anthracene Derivatives

Anthracene derivatives have been used for a wide range of applications and many different synthetic methods for their preparation have been developed. However, despite continued synthetic efforts, introducing substituents in some positions has remained difficult. Here we present a method for the synthesis of 2,3,6,7-substituted anthracene derivatives, one of the most challenging anthracene substitution patterns to obtain. The method is exemplified by the preparation of 2,3,6,7-anthracenetetracarbonitrile and employs a newly developed, stable protected 1,2,4,5-benzenetetracarbaldehyde as the precursor. The precursor can be obtained in two scalable synthetic steps from 2,5-dibromoterephthalaldehyde and is converted into the anthracene derivative by a double intermolecular Wittig reaction under very mild conditions followed by a deprotection and intramolecular double ring-closing condensation reaction. Further modification of the precursor is expected to enable the introduction of additional substituents in other positions and may even enable the synthesis of fully substituted anthracene derivatives by the presented approach.<br>

Chalcones: As potent α-amylase enzyme inhibitors; synthesis, in vitro, and in silico studies

2020 ◽  
Vol 16 ◽  
Author(s):  
Mahboob Ali ◽  
Momin Khan ◽  
Khair Zaman ◽  
Abdul Wadood ◽  
Maryam Iqbal ◽  
...  
Keyword(s):  
In Silico ◽  
Enzyme Inhibitors ◽  
Biological Activities ◽  
Condensation Reaction ◽  
Type Ii Diabetes Mellitus ◽  
Spectroscopic Techniques ◽  
Chalcone Derivatives ◽  
In Silico Studies ◽  
Wide Range

: Background: The inhibition of α-amylase enzyme is one of the best therapeutic approach for the management of type II diabetes mellitus. Chalcone possesses a wide range of biological activities. Objective: In the current study chalcone derivatives (1-17) were synthesized and evaluated their inhibitory potential against α-amylase enzyme. Method: For that purpose, a library of substituted (E)-1-(naphthalene-2-yl)-3-phenylprop-2-en-1-ones was synthesized by ClaisenSchmidt condensation reaction of 2-acetonaphthanone and substituted aryl benzaldehyde in the presence of base and characterized via different spectroscopic techniques such as EI-MS, HREI-MS, 1H-, and 13C-NMR. Results: Sixteen synthetic chalcones were evaluated for in vitro porcine pancreatic α-amylase inhibition. All the chalcones demonstrated good inhibitory activities in the range of IC50 = 1.25 ± 1.05 to 2.40 ± 0.09 μM as compared to the standard commercial drug acarbose (IC50 = 1.34 ± 0.3 μM). Conclusion: Chalcone derivatives (1-17) were synthesized, characterized, and evaluated for their α-amylase inhibition. SAR revealed that electron donating groups in the phenyl ring have more influence on enzyme inhibition. However, to insight the participation of different substituents in the chalcones on the binding interactions with the α-amylase enzyme, in silico (computer simulation) molecular modeling analyses were carried out.

Domino Suzuki coupling and condensation reaction: an efficient strategy towards synthesis of phenanthridines

2015 ◽  
Vol 56 (2) ◽  
pp. 353-355 ◽  
Author(s):  
Munmun Ghosh ◽  
Atiur Ahmed ◽  
Raju Singha ◽  
Jayanta K. Ray
Keyword(s):  
Condensation Reaction ◽  
Suzuki Coupling ◽  
Efficient Strategy

scholarly journals Domino Suzuki-Miyaura Cross-Coupling and Oxidative Condensation Reaction: An Approach Towards Synthesis of Phenanthridine and Its Analogues

2021 ◽  
Author(s):  
Yasin Nuree ◽  
Jayanta Ray
Keyword(s):  
Mutagenic Activity ◽  
Condensation Reaction ◽  
Platinum Complex ◽  
Cross Coupling ◽  
Core Structure ◽  
Synthetic Methods ◽  
Dna Intercalation ◽  
Oxidative Condensation ◽  
The Core ◽  
Anti Tumor Activity

Phenanthridines belong to a very important class of nitrogen containing heterocylic compounds and constitute core structure of many natural alkaloids such as trisphaeridine and nitidine. Quarternarybenzo[c]phenanthridine alkaloids (QBA) represented by sanguinarine(SA), chelerythrine (CHE), and fagaronine (FA) exhibit antifungal and nematocidal properties and also serve as the core structure of broad range of medicinally active molecules showing anti-tumor activity, anti-viral property, anti-neoplastic or mutagenic activity through DNA-intercalation. Phenanthridines are also utilized for the synthesis of compounds of therapeutic interests such as anticancer platinum complex typified by phenanthriplatin antibacterial, anti-infectives, antprotozoal, antituberculosis, antitrypanosomiasis compounds. Although conventional synthetic methods towards their development showed their own advantages, they generally involved either multistep processes with low yield, or starting materials which are not readily available or requirement of prefunctionalization. Hence herein we present the development of an efficient and convenient synthetic methodology towards these versatile compounds. <br>

scholarly journals A New Wave of Amide Bond Formations for Peptide Synthesis

Synthesis ◽  
2019 ◽  
Vol 51 (11) ◽  
pp. 2261-2277 ◽  
Author(s):  
Karlijn Hollanders ◽  
Bert Maes ◽  
Steven Ballet
Keyword(s):  
Carboxylic Acid ◽  
Short Review ◽  
Synthetic Methods ◽  
Amide Bond ◽  
Acid Activation ◽  
New Wave ◽  
Coupling Reagents ◽  
Amide Bonds ◽  
Peptide Chemistry ◽  
Made In

The construction of peptidic amide bonds has become a daily laboratory practice by virtue of well-established ‘coupling reagents’. Nonetheless, inherent limitations connected to these classical coupling methods in terms of waste, safety and expense have yet to be conquered. Research efforts have been devoted to synthetic methods able to surpass these limitations. This short review focuses on the advances made in these ‘non-classical’ methods for amide bond formation with a specific application in peptide chemistry. It consists of two main sections: (i) novel carboxylic activation reagents, and (ii) carboxylic acid and amine surrogates.1 Introduction2 Alternative Carboxylic acid Activation Reagents3 Carboxylic Acid and Amine Surrogates4 Conclusion and Perspectives

scholarly journals Fluorinated phenylalanines: synthesis and pharmaceutical applications

2020 ◽  
Vol 16 ◽  
pp. 1022-1050 ◽  
Author(s):  
Laila Fathy Awad ◽  
Mohammed Salah Ayoup
Keyword(s):  
Amino Acids ◽  
Drug Research ◽  
Enzyme Inhibitors ◽  
Therapeutic Proteins ◽  
Aromatic Amino Acids ◽  
Therapeutic Agents ◽  
Synthetic Methods ◽  
Pharmaceutical Applications ◽  
Recent Advances ◽  
Synthetic Approaches

Recent advances in the chemistry of peptides containing fluorinated phenylalanines (Phe) represents a hot topic in drug research over the last few decades. ᴅ- or ʟ-fluorinated phenylalanines have had considerable industrial and pharmaceutical applications and they have been expanded also to play an important role as potential enzyme inhibitors as well as therapeutic agents and topography imaging of tumor ecosystems using PET. Incorporation of fluorinated aromatic amino acids into proteins increases their catabolic stability especially in therapeutic proteins and peptide-based vaccines. This review seeks to summarize the different synthetic approaches in the literature to prepare ᴅ- or ʟ-fluorinated phenylalanines and their pharmaceutical applications with a focus on published synthetic methods that introduce fluorine into the phenyl, the β-carbon or the α-carbon of ᴅ-or ʟ-phenylalanines.

scholarly journals Catalytic antibodies and enzyme inhibitors

1994 ◽  
Vol 66 (4) ◽  
pp. 703-708 ◽  
Author(s):  
K. D. Janda
Keyword(s):  
Enzyme Inhibitors ◽  
Catalytic Antibodies

scholarly journals NOVEL COMPOUNDS FROM CONDENSATION REACTION BETWEEN 2-ACETYLPYRIDINE AND 2-FORMYLPYRIDINE. SYNTHESIS, CRYSTAL STRUCTURE AND BIOLOGICAL EVALUATION

2019 ◽  
Author(s):  
Roman Vasile Rusnac ◽  
Maria Stefan Botnaru ◽  
Nicanor Barba ◽  
Peter Alexei Petrenko ◽  
Yurii Chumakov ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Condensation Reaction ◽  
Biological Properties ◽  
Biological Evaluation ◽  
Synthetic Methods ◽  
Space Group ◽  
X Ray ◽  
Wide Range ◽  
Atr Spectroscopy ◽  
C Nmr

Two new carbonyl compounds (5-6) were synthesized and spectrally characterized. The reaction mechanism for obtaining the new carbonyl compounds (5-6) was proposed following the analisis retrosintetis reactions of the products and confirmed by 1H and 13C-NMR. Synthesized carbonyl compounds (3-6) can serve as precursors (carbonyls) in the synthesis of thiosemicarbazones, which exhibit a wide range of biological properties. Due the condensation reaction between 2-acetylpyridine and 2-formylpyridine, catalysed with Na2CO3 in aqueous solution and microwave irradiation at 480 W, the product 1,3-bis(pyridin-2-yl)prop-2-en-1-one (3) in a good yield is obtained. By separation on the silica gel column, three products (4-6) were removed. Characterization of novel condensation products between 2-acetylpyridine and 2-formylpyridine was performed by FTIR-ATR spectroscopy, 1H and 13C-NMR spectroscopy, and further confirmed by single crystal X-ray diffraction. Compound (5) crystallise in the space group P-1 and compound (6) in the space group P21/c. Based on the spectral data and X-ray crystallography analysis of the eliminated products, the succession of reactions resulting in compounds (3-6) from (1) and (2) were proposed. Finally, synthetic methods for the preparation of substituted cyclohexanol derivatives have also been proposed. The obtained compounds exhibit moderate antimicrobial and antifungal activity. Antioxidant activity of compounds (4-6) was also studied.

Double Ring-Closing Approach for the Synthesis of 2,3,6,7-Substituted Anthracene Derivatives

2020 ◽  
Author(s):  
Birgit Meindl ◽  
Katharina Pfennigbauer ◽  
Berthold Stöger ◽  
Martin Heeney ◽  
Florian Glöcklhofer
Keyword(s):  
Wittig Reaction ◽  
Condensation Reaction ◽  
Synthetic Methods ◽  
Anthracene Derivative ◽  
Double Ring ◽  
Mild Conditions ◽  
Wide Range ◽  
Anthracene Derivatives

Anthracene derivatives have been used for a wide range of applications and many different synthetic methods for their preparation have been developed. However, despite continued synthetic efforts, introducing substituents in some positions has remained difficult. Here we present a method for the synthesis of 2,3,6,7-substituted anthracene derivatives, one of the most challenging anthracene substitution patterns to obtain. The method is exemplified by the preparation of 2,3,6,7-anthracenetetracarbonitrile and employs a newly developed, stable protected 1,2,4,5-benzenetetracarbaldehyde as the precursor. The precursor can be obtained in two scalable synthetic steps from 2,5-dibromoterephthalaldehyde and is converted into the anthracene derivative by a double intermolecular Wittig reaction under very mild conditions followed by a deprotection and intramolecular double ring-closing condensation reaction. Further modification of the precursor is expected to enable the introduction of additional substituents in other positions and may even enable the synthesis of fully substituted anthracene derivatives by the presented approach.<br>

scholarly journals Domino Suzuki-Miyaura Cross-Coupling and Oxidative Condensation Reaction: An Approach Towards Synthesis of Phenanthridine and Its Analogues

2021 ◽  
Author(s):  
Yasin Nuree ◽  
Jayanta Ray
Keyword(s):  
Mutagenic Activity ◽  
Condensation Reaction ◽  
Platinum Complex ◽  
Cross Coupling ◽  
Core Structure ◽  
Synthetic Methods ◽  
Dna Intercalation ◽  
Oxidative Condensation ◽  
The Core ◽  
Anti Tumor Activity

Phenanthridines belong to a very important class of nitrogen containing heterocylic compounds and constitute core structure of many natural alkaloids such as trisphaeridine and nitidine. Quarternarybenzo[c]phenanthridine alkaloids (QBA) represented by sanguinarine(SA), chelerythrine (CHE), and fagaronine (FA) exhibit antifungal and nematocidal properties and also serve as the core structure of broad range of medicinally active molecules showing anti-tumor activity, anti-viral property, anti-neoplastic or mutagenic activity through DNA-intercalation. Phenanthridines are also utilized for the synthesis of compounds of therapeutic interests such as anticancer platinum complex typified by phenanthriplatin antibacterial, anti-infectives, antprotozoal, antituberculosis, antitrypanosomiasis compounds. Although conventional synthetic methods towards their development showed their own advantages, they generally involved either multistep processes with low yield, or starting materials which are not readily available or requirement of prefunctionalization. Hence herein we present the development of an efficient and convenient synthetic methodology towards these versatile compounds. <br>

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