Synthesis, characterized, QSAR studies and molecular docking of some phosphonates as COVID-19 inhibitors

Gholivand, Khodayar; Barzegari, Azam; Mohammadpanah, Fahimeh; Yaghoubi, Rouhollah; Roohzadeh, Roohollah; Valmoozi, Ali Asghar Ebrahimi

doi:10.1016/j.poly.2022.115824

Cited by 6 publications

(8 citation statements)

References 40 publications

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“…This spectrum shows a multiplet signal at 3.40 ppm related to the NH proton. In the 13 C NMR spectrum of 1, the carbon atoms of the CH 2 groups of five-membered ring are found as two singlet signals at 22.86 and 52.64 ppm, and as a doublet signal at 34.06 ppm with 3 J(P,C) = 6.0 Hz.…”

Section: Ir and Nmr Studymentioning

confidence: 99%

“…Infrared (IR) spectra were prepared by using a Bruker ALPHA FT-IR spectrometer by a KBr disk. 1 H, 13 C, 31 P{ 1 H} NMR spectra were recorded by a NMR Bruker Avance 300 MHz spectrometers and chemical shifts were determined relative to TMS (for 1 H and 13 C) and 85 % H 3 PO 4 (for 31 P) as external standards.…”

Section: Experimental Spectroscopymentioning

confidence: 99%

“…For 2, the 1 H NMR spectrum shows a multiplet peak at the chemical shift of 4.20 ppm for the NÀ H proton and the aromatic hydrogens appear as four multiplet peaks in the range 6.88-8.74 ppm. In the 13…”

Section: Ir and Nmr Studymentioning

confidence: 99%

“…[19,21] With this insight in mind, we present in this study the structures of three new amidophosphoric acid esters, [OCH 2 C-(CH 3 ) 2 CH 2 O]P(O)[X], (X=HNC 5 H 9 (1), NHC 5 H 4 N (2) and NC 4 H 8 (3)) (Scheme 1) determined from single-crystal X-ray crystallography. The spectroscopic properties of these compounds are investigated by FT-IR and 1 H/ 13 C/ 31 P-NMR spectroscopy. The various intermolecular interactions and features of the supramolecular assemblies are examined by 3D Hirshfeld surface maps and 2D fingerprint plots along with the calculated enrichment ratios.…”

Section: Introductionmentioning

confidence: 99%

“…Clinical trials of new anti‐coronavirus drugs request a long time and equipment; therefore computer‐aided drug discovery such as molecular docking simulation which tests the binding interactions between the target protein of virus and the tested drug compound are being used to evaluate the activity of a drug and to accelerate the choice of potential drugs for clinical trials [10,11] . Some suitable antiviral drugs based on phosphoramides and phosphonates such as Tenofovir, Sofosbuvir and Remdesivir have been proposed as anti‐coronavirus agent [12–15] . Moreover, some phosphates‐based compounds were suggested as possible inhibitors against SARS‐CoV‐2 [16] .…”

Section: Introductionmentioning

confidence: 99%

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Structural and Molecular Packing study of Three New Amidophosphoric Acid Esters and Assessment of Their Inhibiting Activity Against SARS‐CoV‐2 by Molecular Docking

2022

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Three new compounds of amidophosphoric acid esters with a [OCH2C(CH3)2CH2O]P(O)[X] segment (where X=cyclopentylamido (1), 2‐aminopyridinyl (2) and pyrrolidinyl (3)) were synthesized and studied using FT‐IR and 31P/13C/1H NMR spectroscopies and single‐crystal X‐ray diffraction analysis. The compounds crystallize in the triclinic space groups Ptrue1‾ for 1 and 3 and in the orthorhombic space group Pca21 for 2, where the asymmetric unit consists of three symmetrically‐independent molecules for 1 and one molecule for 2 and 3. The intermolecular interactions and supramolecular assemblies are assessed by Hirshfeld surface analysis and enrichment ratios. The results reveal that the substituent effect plays an important role in directing the supramolecular structures. The presence of the aromatic substituent aminopyridine in 2 providing the C−H…π interactions leads to a larger variety in interactions including H…H, H…O/O…H, H…C/C…H and H…N/N…H contacts, whereas the packings of the compounds 1 and 3 bearing aliphatic substituents only include H…H and H…O/O…H contacts. The enrichment ratios affirm the importance of O…H/H…O contacts reflecting the hydrogen bond N−H…O interactions to be the enriched contacts. Compounds 1–3 were also investigated along with five similar reported structures with a [OCH2C(CH3)2CH2O]P(O) segment for their inhibitory behavior against SARS‐CoV‐2. The molecular docking results illustrate that the presence of the aromatic amido substituent versus the aliphatic type provides a more favorable condition for their biological activities.

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Section: Ir and Nmr Studymentioning

confidence: 99%

Section: Experimental Spectroscopymentioning

confidence: 99%

Section: Ir and Nmr Studymentioning

confidence: 99%