Phosphorus-nitrogen compounds: part 57—Syntheses of tetrachloro- and tetraaminobenzylspiro(N/N)cyclotriphosphazenes: chemical, structural characterizations, bioactivity and molecular docking studies

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dc.contributor.authorBerberoğlu, İpek
dc.contributor.authorCemaloğlu, Reşit
dc.contributor.authorAsmafiliz, Nuran
dc.contributor.authorKılıç, Zeynel
dc.contributor.authorZeyrek, Celal Tuğrul
dc.contributor.authorAçık, Leyla
dc.contributor.authorKoyunoğlu, Dila
dc.date.accessioned2025-01-21T16:28:13Z
dc.date.available2025-01-21T16:28:13Z
dc.date.issued2022
dc.departmentKırıkkale Üniversitesi
dc.description.abstractAbstract: Despite a significant amount of research in the field of cyclotriphosphazene chemistry, bioactivity and molecular docking studies of this class of cyclotriphosphazenes have still not been adequately studied. In this study, for bioactivity studies, tetrachlorobenzylmonospiro(N/N)cyclotriphosphazenes (4, 5 and 6) were synthesized by the reactions of hexachlorocyclotriphosphazene (N3P3Cl6; trimer; HCCP) with diamines (1, 2 and 3), respectively. Reactions of 4, 5 and 6 with excess pyrrolidine, piperidine, morpholine and 1, 4-dioxa-8-azaspiro[4.5]decane (DASD) gave the tetrapyrrolidino (7, 8 and 9), tetrapiperidino (10, 11 and 12), tetramorpholino (13, 14 and 15) and tetraDASD (16, 17 and 18) substituted benzylmonospiro(N/N)cyclotriphosphazenes. Microanalytical, spectral and crystallographic data (for 6 and 15) revealed the structures of the cyclotriphosphazenes. Antibacterial and antifungal activities of all phosphazenes against selected strains of bacteria and yeast, and pBR322 plasmid DNA cleavage activities were discussed. MIC values of 11 and 12 (78.1 and 156.3 µM, respectively) against C. albicans are higher than the reference antibiotic Ketoconazole. Cytotoxic activities of five phosphazenes against L929 Fibroblast and DLD-1 cells were evaluated. Additionally, Density Functional Theory (DFT) calculations of 6 and 15 were performed. Molecular docking studies of 6 and 15 with DNA, endonuclease BamHI, S. aureus Dihydrofolate Reductase and E. coli DNA gyrase were presented. Graphical abstract: [Figure not available: see fulltext.] © 2022, The Author(s), under exclusive licence to Springer Nature B.V.
dc.description.sponsorshipTÜBA; Türkiye Bilimsel ve Teknolojik Araştırma Kurumu, TÜBİTAK, (116Z400); Türkiye Bilimler Akademisi; Hacettepe Üniversitesi, (013 D04 602 004)
dc.identifier.doi10.1007/s11164-022-04746-1
dc.identifier.endpage3219
dc.identifier.issn0922-6168
dc.identifier.issue7
dc.identifier.scopus2-s2.0-85131873683
dc.identifier.scopusqualityQ2
dc.identifier.startpage3189
dc.identifier.urihttps://doi.org/10.1007/s11164-022-04746-1
dc.identifier.urihttps://hdl.handle.net/20.500.12587/23513
dc.identifier.volume48
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherSpringer Science and Business Media B.V.
dc.relation.ispartofResearch on Chemical Intermediates
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_20241229
dc.subjectAntimicrobial activity; Cytotoxicity; DNA cleavage; Molecular docking; Monospirocyclotriphosphazenes
dc.titlePhosphorus-nitrogen compounds: part 57—Syntheses of tetrachloro- and tetraaminobenzylspiro(N/N)cyclotriphosphazenes: chemical, structural characterizations, bioactivity and molecular docking studies
dc.typeArticle

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