A pyrazinamide-benzenesulfonohydrazide hybrid N'-(phenylsulfonyl)pyrazine-2-carbohydrazonamide: Experimental and theoretical insights
Küçük Resim Yok
Tarih
2024
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Elsevier Ltd
Erişim Hakkı
info:eu-repo/semantics/closedAccess
Özet
A pyrazinamide-benzenesulfonohydrazide hybrid N'-(phenylsulfonyl)pyrazine-2-carbohydrazonamide (1), which was studied by physical measurements and computational tools, is reported. Compound 1 was synthesized using a metallic Na-assisted interaction of 2-cyanopyrazine with benzenesulfonylhydrazine in dry methanol. Our newly developed synthetic approach allowed to obtain the title compound witht the yield of 74%, which is more than twice higher in comparison to the previously reported synthesis using pyrazine-2-carbohydrazonamide and benzenesulfonyl chloride. Molecules of the title compound are linked via N–H⋯O, C–H⋯Ph, S=O⋯2-pyrazine and π⋯π interactions. As it was found by the Hirshfeld surface analysis, molecules of 1 interact through H⋯X (X = H, C, N and O) contacts. Electronic properties of 1 were revealed using the Density Functional Theory (DFT) computations. 1 was expected to be a fourth-class toxicity, and it does not penetrate the blood-brain barrier, while can potentially be absorbed by the gastrointestinal tract. It was predicted that compound 1, which demonstrated the strongest activity against PLpro, Nsp3_range 207–379 MES and Nsp16_SAM site, are of interest to suppress activity of the SARS-CoV-2 proteins. Although the Ki value is slightly higher, the ligand efficiency scores for complex PLpro–1 were found to be characteristic for a Hit. © 2024 Elsevier Ltd
Açıklama
Anahtar Kelimeler
ADMET, Benzenesulfonylhydrazine, DFT, Hirshfeld Surface Analysis, Pyrazine, X-Ray
Kaynak
Tetrahedron
WoS Q Değeri
Q2
Scopus Q Değeri
Q3
Cilt
162
Sayı
Künye
Alizadeh, V., Garcia-Santos, I., Castiñeiras, A., Mahmoudi, G., & Safin, D. A. (2024). A pyrazinamide-benzenesulfonohydrazide hybrid N'-(phenylsulfonyl) pyrazine-2-carbohydrazonamide: experimental and theoretical insights. Tetrahedron, 134066.
