Phosphorus-nitrogen compounds. Part 56. Comparative syntheses and spectral properties of multiheterocyclic 2-cis-4-ansa and spiro-ferrocenyl (N/O)cyclotetraphosphazenes: Antituberculosis and antimicrobial activity and DNA interaction studies. (2nd January 2022)

• Record Type: Journal Article
• Authors: Binici, Arzu; Okumuş, Aytuğ; Yakut, Mehtap; Elmas, Gamze; Kılıç, Zeynel; Koyunoğlu, Dila; Açık, Leyla; Şimşek, Hülya
• Is Part Of: Phosphorus, sulfur, and silicon and the related elements. Volume 197:Number 1(2022)
• Page Start: 18
• Page End: 29
• Publication Date: 2022-01-02
• Subjects: Mono-ferrocenyl-ansa/spirocyclotetraphosphazenes -- spectroscopy -- antimicrobial activity -- DNA interactions -- antituberculosis activity; Sulfur compounds -- Periodicals; Organosulfur compounds -- Periodicals; Phosphorus compounds -- Periodicals; Organophosphorus compounds -- Periodicals; Silicon compounds -- Periodicals; Organosilicon compounds -- Periodicals; 546
• DOI: 10.1080/10426507.2021.1986502
• Languages: English
• ISSNs: 1042-6507

Abstract

Abstract: In the present study, two types of starting compounds; hexachloro(N/O)-cyclotetraphosphazenes containing mono-ferrocenyl-pendant arm, namely, mono-ferrocenyl-2- cis -4-dichloro-ansa-(2, 4-ansa; 2 ) and mono-ferrocenyl-spiro-(spiro; 3 ) were prepared by the reaction of N4 P4 Cl8 (1 ) with sodium 3-( N- ferrocenylmethylamino)-1-propanoxide (L ). Reactions of 2, 4-ansa (2 ) with excess benzylamine and n- hexylamine resulted in the formation of partly substituted 2- cis -4-dichloro-ansa-cyclotetraphosphazenes (2a and 2b ). In contrast, spiro (3 ) gave fully substituted mono-ferrocenyl-spiro-cyclotetraphosphazenes (3a and 3b ) with excess benzylamine and n-hexylamine. As expected, the 2, 4-ansa cyclotetraphosphazenes (2, 2a, and 2b ) have two distinct stereogenic P-centers. The structures of cyclotetraphosphazenes were evaluated by elemental analysis, ESI-MS, FTIR, 1 H, 13 C, and 31 P-NMR techniques. The antibacterial and antifungal activities against some selected bacteria and yeast strains, antituberculosis activities against Mycobacterium tuberculosis H37Rv, and DNA cleavage activities of mono-ferrocenyl-cyclotetraphosphazenes were also discussed. Compounds 2b, 3a, and 3b exhibited antifungal activity against C. albicans (MIC= 156.3 µM) higher than reference antibiotic Ketoconazole. Moreover, four compounds displayed antituberculosis activity against the M. tuberculosis H37RV. Compound 2a (20 μg/mL) is the most potent of the four compounds. Graphical abstract: UF0001