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


Binici A., OKUMUŞ A., Yakut M., ELMAS G., KILIÇ Z., Koyunoglu D., ...More

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2021 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Publication Date: 2021
  • Doi Number: 10.1080/10426507.2021.1986502
  • Title of Journal : PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  • Keywords: Mono-ferrocenyl-ansa, spirocyclotetraphosphazenes, spectroscopy, antimicrobial activity, DNA interactions, antituberculosis activity, STEREOGENIC PROPERTIES, STRUCTURAL CHARACTERIZATIONS, CYTOTOXIC ACTIVITIES, CRYSTAL-STRUCTURES, DERIVATIVES, SALTS

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 N4P4Cl8 (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, H-1, C-13, and P-31-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 mu M) higher than reference antibiotic Ketoconazole. Moreover, four compounds displayed antituberculosis activity against the M. tuberculosis H37RV. Compound 2a (20 mu g/mL) is the most potent of the four compounds.