New thiophene-derived α-aminophosphonic acids: Synthesis under microwave irradiations, antioxidant and antifungal activities, DFT investigations and SARS-CoV-2 main protease inhibition

Tlidjane, Hamida; Chafai, Nadjib; Chafaa, Salah; Bensouici, Chawki; Benbouguerra, Khalissa

doi:10.1016/j.molstruc.2021.131853

Cited by 33 publications

(11 citation statements)

References 47 publications

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“…On the other hand, the DFT calculations and Computer aided design of various derivatives of α-aminophosphonates have been widely described. [46][47][48][49] In this context, we have addressed and discussedthe DFT study based on B3LYP/6-31G (d, p) of four synthesized trimethoxy α-aminophosphonates derivatives (4 j, 4 k, 4 l and 4 m) as novel compounds. The HOMO and LUMO orbitals energies and the calculated molecular electrostatic potential (MEP) have been performed to examine the reactivity of the studied molecules.…”

Section: Introductionmentioning

confidence: 99%

“…On the other hand, the DFT calculations and Computer aided design of various derivatives of α ‐aminophosphonates have been widely described [46–49] . In this context, we have addressed and discussedthe DFT study based on B3LYP/6‐31G (d, p) of four synthesized trimethoxy α‐ aminophosphonates derivatives ( 4 j , 4 k , 4 l and 4 m ) as novel compounds.…”

Section: Introductionmentioning

confidence: 99%

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SB‐2 cationic resin: an efficient and reusable organocatalyst for the synthesis of α‐aminophosphonates, DFT calculations and, computer aided design in antifungal activity

Touil,

Guezane‐Lakoud,

Boukachabia

et al. 2024

ChemistrySelect

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SB‐2 cationic resin has been employed as an unexpected and reusable heterogeneous organocatalyst in multicomponents reaction for the synthesis of the α‐aminophosphonates derivatives that act as antifungal agents, this reaction proceeds under eco‐friendly and simple procedure by condensation in one pot of substituted aromatic aldehydes, anilines and diethylphosphite. Excellent isolated product yields are obtained (up to 70 %) for (4 a–o) within shorter reaction times in solvent‐free condition. The synthesized compounds were determined by spectroscopic analyses such as: NMR (1H, 13C and 31P), IR and HRMS.Molecular geometries, electronic properties, stability and reactivity such as: HOMO/LUMO, , dipole moment (6.1308<D<10.5829), electronegativity (2.3490<X<3.5892), electrophilicity (1.1046<ω<3.2185) and the calculated thermodynamic descriptors (Zero‐point Energies, Enthalpy and Gibbs Free Energy) of four trimethoxy α‐aminophosphonates derivatives (4 j, 4 k, 4 l and 4 m) were carried by DFT at B3LYP 6‐31G (d, p) basis set. Computer aided design by molecular docking of studied compounds revealed a good binding energy against 5HS1 receptor to be considered as antifungal candidates and compared with Voriconazole. In additionally, druglikeness parameters of selected compounds were found through in silico pharmacological ADME/T properties estimation.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

SB‐2 cationic resin: an efficient and reusable organocatalyst for the synthesis of α‐aminophosphonates, DFT calculations and, computer aided design in antifungal activity

Touil,

Guezane‐Lakoud,

Boukachabia

et al. 2024

ChemistrySelect

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“… 18 Of a variety of heterocycles, coumarin-, 19 – 24 1,2,4-triazole- 25 , 26 and thiophene-derived compounds have also been found to be of interest against COVID-19. 27 – 29 Thus, a combination of the above-mentioned heterocycles in a single molecule seems to be of value for the fabrication of an active agent used in the COVID-19 therapy.…”

Section: Introductionmentioning

confidence: 99%

A novel coumarin-triazole-thiophene hybrid: synthesis, characterization, ADMET prediction, molecular docking and molecular dynamics studies with a series of SARS-CoV-2 proteins

et al. 2023

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Synthesis, characterization and theoretical studies of a novel coumarin-triazole-thiophene hybrid 4-(((4-ethyl-5-(thiophen-2-yl)-4 H -1,2,4-triazol-3-yl)thio)methyl)-6,7-dimethyl-2 H -chromen-2-one ( 1 ), which was fabricated from 4-ethyl-5-(thiophen-2-yl)-4 H -1,2,4-triazole-3-thiol and 4-(chloromethyl)-6,7-dimethyl-2 H -chromen-2-one, are reported. The resulting compound was characterized by microanalysis, IR, 1 H, and 13 C APT NMR spectroscopy. The DFT calculations examined the structure and electronic properties of 1 in gas phase. Its reactivity descriptors and molecular electrostatic potential revealed the reactivity and the reactive centers of 1 . ADMET properties of 1 were evaluated using the respective online tools. It was established that 1 exhibit positive gastrointestinal absorption properties and negative human blood-brain barrier penetration. The Toxicity Model Report revealed that 1 belongs to toxicity class 4. Molecular docking was additionally applied to study the interaction of 1 with some SARS-CoV-2 proteins. It was established that the title compound is active against all the applied proteins with the most efficient interaction with Papain-like protease (PLpro). The interaction of 1 with the applied proteins was also studied using molecular dynamics simulations. Graphical abstract A novel coumarin-triazole-thiophene hybrid 4-(((4-ethyl-5-(thiophen-2-yl)-4H-1,2,4-triazol-3-yl)thio)methyl)-6,7-dimethyl-2H-chromen-2-one ( 1 ) is reported. The structure and electronic properties of 1 were examined by the DFT calculations. ADMET properties of 1 were also evaluated. Molecular docking and molecular dynamics simulations were applied to study interactions of 1 with a series of the SARS-CoV-2 proteins. Supplementary Information The online version contains supplementary material available at 10.1007/s12039-022-02127-0.

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“…In the past decade, organophosphorus and derivatives compounds have been of great interest and have found a wide range of applications in the areas of medicinal, industrial chemistry, and agricultural, based on their interesting biological and physical properties, as well as their utility as a synthetic intermediate. [1,4] Especially, α-aminophosphonates compounds exhibit excellent therapeutic and pharmaceutical properties, [5,10] due to their-isosteres with α-amino acids [11,12] such anticancer drugs, [13,14] haptens of catalytic antibodies, [15,16] antifungals, [17] anti-HIV agents, [18] enzymes inhibitors, [19] antiviral, [20,21] antiinflammatory, [22] anti-Alzheimer, [23] antioxidant, [24] antimalarial, [25] and inhibition of carbonic anhydrase. [26,27] The importance of αaminophosphonates is illustrated by the publications of several reviews per year.…”

Section: Introductionmentioning

confidence: 99%

A New family of Sulfamidophosphonates Derivatives: Microwave‐Accelerated Multicomponent Synthesis, Characterization and X‐Ray Crystallographic Study**

et al. 2023

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In this present study, we describe a simple, effective and greener one‐pot microwave‐assisted synthesis of novel α‐sulfamidophosphonates 4(a–l), and 5(a, b) that were rationally designed and synthesized following the principle of the superposition of bioactives substructures. This reaction was accomplished by the condensation of various aromatic aldehydes, sulfamide and diethyl phosphite via the Kabachnik‐Fields reaction using ethanol as solvent under catalyst‐free conditions. The corresponding products were obtained with good yields, in short reactions time and no side product was observed. All the newly synthesized compounds were systematically characterized by IR, 1H NMR, 13C NMR and 31P NMR analysis and the structures of the compounds 4 b and 4 c were further analyzed by single crystal X‐ray diffraction.

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New thiophene-derived α-aminophosphonic acids: Synthesis under microwave irradiations, antioxidant and antifungal activities, DFT investigations and SARS-CoV-2 main protease inhibition

Cited by 33 publications

References 47 publications

SB‐2 cationic resin: an efficient and reusable organocatalyst for the synthesis of α‐aminophosphonates, DFT calculations and, computer aided design in antifungal activity

SB‐2 cationic resin: an efficient and reusable organocatalyst for the synthesis of α‐aminophosphonates, DFT calculations and, computer aided design in antifungal activity

A novel coumarin-triazole-thiophene hybrid: synthesis, characterization, ADMET prediction, molecular docking and molecular dynamics studies with a series of SARS-CoV-2 proteins

A New family of Sulfamidophosphonates Derivatives: Microwave‐Accelerated Multicomponent Synthesis, Characterization and X‐Ray Crystallographic Study**

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