Phosphorus-nitrogen compounds. Part 88. Design and preparation of fully substituted mono(4-nitrobenzyl)spiro(N/N)cyclotriphosphazenes: Chemical, structural investigation, carbonic anhydrase activation and free radical scavenging activity studies
Inorganica Chimica Acta, cilt.604, 2027 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 604
- Basım Tarihi: 2027
- Doi Numarası: 10.1016/j.ica.2026.123444
- Dergi Adı: Inorganica Chimica Acta
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core, Chimica, Compendex, Academic Search Ultimate (EBSCO), Engineering Source (EBSCO)
- Anahtar Kelimeler: Antioxidant activity, Carbonic anhydrase activity, Crystallography, Mono(4-nitrobenzyl)spiro(N/N)cyclotriphosphazene, Spectroscopy
- Ankara Üniversitesi Adresli: Evet
Özet
Substitution reactions of hexachlorocyclotriphosphazene (N3P3Cl6 HCCP, 1) with N-alkyl-N′-mono(4-nitrobenzyl)diamines, NO2PhCH2NH(CH2)nNHR1 (R1 = CH3, n = 2; L1, R1 = C2H5, n = 2; L2, R1 = CH3, n = 3; L3), gave the starting compounds tetrachloromono(4-nitrobenzyl)monospiro(N/N)cyclotriphosphazenes (2–4). Tetrakis(4-hydroxycoumarino)mono(4-nitrobenzyl)spiro(N/N)cyclotriphosphazenes 2a, 3a and 4a were prepared from the replacement reactions of 2, 3 and 4 with excess 4-hydroxycoumarin in dry THF in the presence of Cs2CO3, respectively. Due to its highest yield among the three starting compounds, tetrachlorophosphazene 4 was treated with n-butylamine and benzimidazole, respectively, to synthesize the fully substituted products (4b and 4c). Elemental analysis, HRMS, FTIR, 13C, 1H and 31P NMR techniques were used for the characterization of novel cyclotriphosphazenes. The solid-state crystal structures of 2a and 3 were confirmed using the X-ray crystallography. In addition, Hirshfeld surface (HS) analyses were performed to determine the intermolecular interactions in these crystals. Furthermore, the carbonic anhydrase activation on hCA I and hCA II isoenzymes and free radical scavenging activity (FRSA, antioxidant) of the phosphazenes were scrutinized. Based on the in vitro activator effects of these compounds, compound 4a demonstrated the highest hCA activator potency (hCA I KA = 39.67 ± 1.99 μM and hCA II KA = 38.54 ± 2.06 μM). However, compound 4c exhibits high isoform hCA II selectivity (hCA II KA = 79.65 ± 5.11 μM). Compound 4b (69.3 ± 0.3%) displayed the highest FRSA among the derivatives, its activity approaching that of the standard antioxidants BHA (93.3 ± 0.3%) and α-tocopherol (97.6 ± 0.0%).