Discovery of Novel α-Aminophosphonates with Hydrazone as Potential Antiviral Agents Combined With Active Fragment and Molecular Docking

Tian, Jing; Ji, Renjing; Wang, Huan; Li, Siyu; Zhang, Guoping

doi:10.3389/fchem.2022.911453

Cited by 14 publications

(6 citation statements)

References 40 publications

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“…Several α -aminophosphonate derivatives, exhibiting interesting biological properties, have previously been synthesized ( El-Boraey et al, 2015 ; Gundluru et al, 2021 ; Tian et al, 2022 ). Many studies have reported their potential as antiviral agents ( Hu et al, 2008 ; Song et al, 2010 ; Amira et al, 2021 ).…”

Section: Resultsmentioning

confidence: 99%

Theoretical exploration on structures, bonding aspects and molecular docking of α-aminophosphonate ligated copper complexes against SARS-CoV-2 proteases

et al. 2022

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Recent years have witnessed a growing interest in the biological activity of metal complexes of α-aminophosphonates. Here for the first time, a detailed DFT study on five α-aminophosphonate ligated mononuclear/dinuclear CuII complexes is reported using the dispersion corrected density functional (B3LYP-D2) method. The electronic structures spin densities, FMO analysis, energetic description of spin states, and theoretical reactivity behaviour using molecular electrostatic potential (MEP) maps of all five species are reported. All possible spin states of the dinuclear species were computed and their ground state S values were determined along with the computation of their magnetic coupling constants. NBO analysis was also performed to provide details on stabilization energies. A molecular docking study was performed for the five complexes against two SARS-CoV-2 coronavirus protein targets (PDB ID: 6LU7 and 7T9K). The docking results indicated that the mononuclear species had a higher binding affinity for the targets compared to the dinuclear species. Among the species investigated, species I showed the highest binding affinity with the SARS-CoV-2 Omicron protease. NPA charge analysis showed that the heteroatoms of model species III had a more nucleophilic nature. A comparative study was performed to observe any variations and/or correlations in properties among all species.

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Section: Resultsmentioning

confidence: 99%

Theoretical exploration on structures, bonding aspects and molecular docking of α-aminophosphonate ligated copper complexes against SARS-CoV-2 proteases

et al. 2022

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“…The treatment, protection, and passivation of compound 60 against TMV were 33.2%, 65.1%, and 45.7%, while, for compound 61 against TMV, they were 74.3%, 78.7%, and 94.3%. Molecular docking found that benzothiazole rings are important for the antiviral activity of these compounds, and the hydrazone’s structure can affect the compounds’ antiviral activity [ 100 ]. The combination of benzothiazoles with diesters or amino phosphonate had good antiviral activity, which showed the advantage of the skeleton structure in antiviral activity.…”

Section: Antiviral Activitymentioning

confidence: 99%

Research Progress of Benzothiazole and Benzoxazole Derivatives in the Discovery of Agricultural Chemicals

Zou

Zhang

Xing

et al. 2023

IJMS

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Benzoxazole and benzothiazole have a broad spectrum of agricultural biological activities, such as antibacterial, antiviral, and herbicidal activities, which are important fused heterocyclic scaffold structures in agrochemical discovery. In recent years, great progress has been made in the research of benzoxazoles and benzothiazoles, especially in the development of herbicides and insecticides. With the widespread use of benzoxazoles and benzothiazoles, there may be more new products containing benzoxazoles and benzothiazoles in the future. We systematically reviewed the application of benzoxazoles and benzothiazoles in discovering new agrochemicals in the past two decades and summarized the antibacterial, fungicidal, antiviral, herbicidal, and insecticidal activities of the active compounds. We also discussed the structural–activity relationship and mechanism of the active compounds. This work aims to provide inspiration and ideas for the discovery of new agrochemicals based on benzoxazole and benzothiazole.

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“…Compounds containing an aminophosphonic unit display a wide spectrum of biological activity ( Figure 4 ), e.g., antiproliferative [ 28 , 29 , 30 , 31 ], antimicrobial [ 32 , 33 , 34 ], antiviral [ 35 , 36 ], antioxidant [ 37 , 38 , 39 , 40 ], anti-inflammatory [ 37 , 41 , 42 ] and they act as inhibitors of various enzymes such as acetylcholinesterase [ 43 , 44 , 45 ], aminopeptidases [ 46 , 47 ] or α-glucosidase [ 48 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Enantiomerically Enriched Protected 2-Amino-, 2,3-Diamino- and 2-Amino-3-Hydroxypropylphosphonates

2023

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Simple and efficient strategies for the syntheses of enantiomerically enriched functionalized diethyl 2-amino-, 2,3-diamino- and 2-amino-3-hydroxypropylphosphonates have been developed starting from, respectively, N-protected (aziridin-2-yl)methylphosphonates, employing a regioselective aziridine ring-opening reaction with corresponding nucleophiles. Diethyl (R)- and (S)-2-(N-Boc-amino)propylphosphonates were obtained via direct regiospecific hydrogenolysis of the respective enantiomer of (R)- and (S)-N-Boc-(aziridin-2-yl)methylphosphonates. N-Boc-protected (R)- and (S)-2,3-diaminopropylphosphonates were synthesized from (R)- and (S)-N-Bn-(aziridin-2-yl)methylphosphonates via a regiospecific ring-opening reaction with neat trimethylsilyl azide and subsequent reduction of (R)- and (S)-2-(N-Boc-amino)-3-azidopropylphosphonates using triphenylphosphine. On the other hand, treatment of the corresponding (R)- and (S)-N-Bn-(aziridin-2-yl)methylphosphonates with glacial acetic acid led regiospecifically to the formation of (R)- and (S)-2-(N-Bn-amino)-3-acetoxypropylphosphonates.

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Discovery of Novel α-Aminophosphonates with Hydrazone as Potential Antiviral Agents Combined With Active Fragment and Molecular Docking

Cited by 14 publications

References 40 publications

Theoretical exploration on structures, bonding aspects and molecular docking of α-aminophosphonate ligated copper complexes against SARS-CoV-2 proteases

Theoretical exploration on structures, bonding aspects and molecular docking of α-aminophosphonate ligated copper complexes against SARS-CoV-2 proteases

Research Progress of Benzothiazole and Benzoxazole Derivatives in the Discovery of Agricultural Chemicals

Synthesis of Enantiomerically Enriched Protected 2-Amino-, 2,3-Diamino- and 2-Amino-3-Hydroxypropylphosphonates

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