A pyrazinamide-benzenesulfonohydrazide hybrid N'-(phenylsulfonyl)pyrazine-2-carbohydrazonamide: Experimental and theoretical insights

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dc.authoridGhodrat Mahmoudi / 0000-0002-4846-5283
dc.authorscopusidGhodrat Mahmoudi / 15765751200
dc.authorwosidGhodrat Mahmoudi / AAB-6892-2022
dc.contributor.authorAlizadeh, Vali
dc.contributor.authorGarcia Santos, Isabel
dc.contributor.authorCastiñeiras, Alfonso
dc.contributor.authorMahmoudi, Ghodrat
dc.contributor.authorSafin, Damir A
dc.date.accessioned2025-04-18T08:43:06Z
dc.date.available2025-04-18T08:43:06Z
dc.date.issued2024
dc.departmentİstinye Üniversitesi, Mühendislik ve Doğa Bilimleri Fakültesi, Kimya Bölümü
dc.description.abstractA 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
dc.identifier.citationAlizadeh, 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.
dc.identifier.doi10.1016/j.tet.2024.134066
dc.identifier.issn10.1016/j.tet.2024.134066
dc.identifier.scopus2-s2.0-85196283998
dc.identifier.scopusqualityQ3
dc.identifier.urihttp://dx.doi.org/10.1016/j.tet.2024.134066
dc.identifier.urihttps://hdl.handle.net/20.500.12713/6596
dc.identifier.volume162
dc.identifier.wosWOS:001325327000001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakScopus
dc.indekslendigikaynakWeb of Science
dc.institutionauthorMahmoudi, Ghodrat
dc.institutionauthoridGhodrat Mahmoudi / 0000-0002-4846-5283
dc.language.isoen
dc.publisherElsevier Ltd
dc.relation.ispartofTetrahedron
dc.relation.publicationcategoryKitap Bölümü - Uluslararası
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectADMET
dc.subjectBenzenesulfonylhydrazine
dc.subjectDFT
dc.subjectHirshfeld Surface Analysis
dc.subjectPyrazine
dc.subjectX-Ray
dc.titleA pyrazinamide-benzenesulfonohydrazide hybrid N'-(phenylsulfonyl)pyrazine-2-carbohydrazonamide: Experimental and theoretical insights
dc.typeArticle

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