A novel tetrazole-1,8-naphthyridine-amide hybrid: First structurally characterized tetrazolo[1,5-a]-derivative of naphthyridines with a luminescence activity, potency against COVID-19, and anticancer activity

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dc.authoridNath, Sourav/0009-0003-5264-7965
dc.authoridSahin, Onur/0000-0003-3765-3235
dc.authoridBorah, Pranab/0000-0002-5476-1636
dc.authoridADHIKARI, SUMAN/0000-0002-6382-5400
dc.contributor.authorAdhikari, Suman
dc.contributor.authorNath, Sourav
dc.contributor.authorSen, Tanushree
dc.contributor.authorRaza, Rameez
dc.contributor.authorSahin, Onur
dc.contributor.authorEftekhari-Sis, Bagher
dc.contributor.authorMahmoudi, Ghodrat
dc.date.accessioned2025-03-23T19:39:18Z
dc.date.available2025-03-23T19:39:18Z
dc.date.issued2025
dc.departmentSinop Üniversitesi
dc.description.abstractThis contribution is devoted to a novel tetrazole-1,8-naphthyridine-amide hybrid N-(tetrazolo[1,5-a][1,8] naphthyridin-8-yl)butyramide (1), which was produced from N-(7-chloro-1,8-naphthyridin-2-yl)butyramide by reacting with NaN3. In the crystalline state, molecules of 1 exhibited C-H center dot center dot center dot O intramolecular bonds and produced a 1D chain through N-H center dot center dot center dot N and C-H center dot center dot center dot N contacts. Chains produce a supramolecular 2D layer due to pi center dot center dot center dot pi interactions. In the UV-vis spectrum, 1 exhibits bands up to similar to 360 nm and is emissive with a broad band from about 335 to 450 nm, with the maximum at 365 nm. Fine features of 1 were revealed using the density functional theory (DFT) calculations in water. The computed geometrical parameters are in accordance with the experimental values. The frontier electronic orbitals were found on the molecule except for the propyl fragment, and 1 was determined as a strong electrophile. The computed absorption, distribution, metabolism, elimination and toxicity (ADMET) features predicted positive gastrointestinal absorption (GA) activity and negative human blood-brain barrier (BBB) property of 1. Compound 1 in silico tested to inhibit some of the severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) proteins. Papain-like protease (PLpro) and Nonstructural protein 3 (Nsp3_range 207-379-MES) were established to interact with 1 more efficiently. The PLpro complex with 1 exhibits a ligand efficiency scores for a Hit. The present study also delved into elucidating the cytotoxic potential of compound 1 in Dalton's Lymphoma (DL) malignant cancer cell lines, aiming to explore its anticancer efficacy. Furthermore, this investigation extends its purview to scrutinize the cytotoxicity profile of the aforementioned compound on normal peripheral blood mononuclear cells (PBMCs), thus enabling a comprehensive comparative analysis of cellular responses under both neoplastic and non-neoplastic cell lines.
dc.identifier.doi10.1016/j.molstruc.2024.139803
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85204705480
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2024.139803
dc.identifier.urihttps://hdl.handle.net/11486/6315
dc.identifier.volume1321
dc.identifier.wosWOS:001324402600001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectTetrazole
dc.subjectNaphthyridine
dc.subjectX-ray analysis
dc.subjectTheoretical computations
dc.subjectCOVID-19
dc.subjectAnticancer agent
dc.titleA novel tetrazole-1,8-naphthyridine-amide hybrid: First structurally characterized tetrazolo[1,5-a]-derivative of naphthyridines with a luminescence activity, potency against COVID-19, and anticancer activity
dc.typeArticle

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