Phosphorus-nitrogen compounds. Part 56. Comparative syntheses and spectral properties of multiheterocyclic 2-<i>cis</i>-4-ansa and spiro-ferrocenyl (N/O)cyclotetraphosphazenes: Antituberculosis and antimicrobial activity and DNA interaction studies
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, cilt.197, sa.1, ss.18-29, 2022 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 197 Sayı: 1
- Basım Tarihi: 2022
- Doi Numarası: 10.1080/10426507.2021.1986502
- Dergi Adı: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Index Chemicus (IC)
- Sayfa Sayıları: ss.18-29
- Anahtar Kelimeler: Mono-ferrocenyl-ansa, spirocyclotetraphosphazenes, spectroscopy, antimicrobial activity, DNA interactions, antituberculosis activity, STEREOGENIC PROPERTIES, STRUCTURAL CHARACTERIZATIONS, CYTOTOXIC ACTIVITIES, CRYSTAL-STRUCTURES, DERIVATIVES, SALTS
- Ankara Üniversitesi Adresli: Evet
Özet
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.