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.authoridZeyrek, Celal Tugrul/0000-0001-6744-7841
dc.authoridHokelek, Tuncer/0000-0002-8602-4382
dc.authorid, RESIT/0000-0002-2802-0754
dc.authoridAcik, Leyla/0000-0002-3672-8429
dc.contributor.authorBerberoglu, Ipek
dc.contributor.authorCemaloglu, Resit
dc.contributor.authorAsmafiliz, Nuran
dc.contributor.authorKilic, Zeynel
dc.contributor.authorZeyrek, Celal Tugrul
dc.contributor.authorAcik, Leyla
dc.contributor.authorKoyunoglu, Dila
dc.date.accessioned2025-01-21T16:43:26Z
dc.date.available2025-01-21T16:43:26Z
dc.date.issued2022
dc.departmentKırıkkale Üniversitesi
dc.description.abstractDespite 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 mu M, 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. [GRAPHICS] .
dc.description.sponsorshipScientific and Technical Research Council of Turkey [116Z400]; Turkish Academy of Sciences (TUBA); Hacettepe University Scientific Research Project Unit [013 D04 602 004]
dc.description.sponsorshipThe authors acknowledge the Scientific and Technical Research Council of Turkey Grant No.116Z400. Z. K. thanks the Turkish Academy of Sciences (TUBA) for partial support of this work. T. H. is grateful to Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004). The numerical calculations reported in this paper were fully/partially performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources).
dc.identifier.doi10.1007/s11164-022-04746-1
dc.identifier.endpage3219
dc.identifier.issn0922-6168
dc.identifier.issn1568-5675
dc.identifier.issue7
dc.identifier.startpage3189
dc.identifier.urihttps://doi.org/10.1007/s11164-022-04746-1
dc.identifier.urihttps://hdl.handle.net/20.500.12587/25270
dc.identifier.volume48
dc.identifier.wosWOS:000810324700002
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.language.isoen
dc.publisherSpringer
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.subjectMonospirocyclotriphosphazenes; Cytotoxicity; Antimicrobial activity; DNA cleavage; Molecular docking
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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