Phosphorus-Nitrogen compounds part 47: The conventional and microwave-assisted syntheses of dispirocyclotriphosphazene derivatives with (4-fluoro/4-nitrobenzyl) pendant arms: Structural and stereogenic properties and DNA interactions

Tanrikulu G. I., YAKUT M., OKUMUŞ A., Kilic Z., HÖKELEK T., AYDIN B., ...Daha Fazla

INORGANICA CHIMICA ACTA, cilt.490, ss.179-189, 2019 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 490
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1016/j.ica.2019.03.018
  • Dergi Adı: INORGANICA CHIMICA ACTA
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.179-189
  • Anahtar Kelimeler: Dispirocyclotriphosphazenes, Crystallography, Stereoisomers, Spectroscopy, BRIDGED CYCLOTRIPHOSPHAZENE DERIVATIVES, ANTIMICROBIAL ACTIVITIES, BIOLOGICAL-ACTIVITIES, SPIRO-ANSA, STEREOCHEMICAL ASPECTS, CHIRAL CONFIGURATIONS, CYTOTOXIC ACTIVITIES, CRYSTAL-STRUCTURES, RAMAN-SPECTRA, ANTITUBERCULOSIS
  • Ankara Üniversitesi Adresli: Evet

Özet

The Cl exchange reactions of hexachlorocyclotriphosphazene, N3P3Cl6, with two equimolar amounts of N-alkyl-N'-mono(4-fluorobenzyl)diamines (1-3), FC6H4CH2NH(CH2)(n)NHR1 (n=2 and 3, R-1=CH3 or C2H5), and N-alkyl-N'-mono(4-nitrobenzyl)diamines (4 and 5), NO2C6H4CH2NH(CH2)(n)NHR1 (n= 2, R-1= CH3 or C2H5), led to the formation of the mono(4-fluorobenzyl) (1a-3a) and mono(4-nitrobenzyl) (4a and 5a) spirocyclotriphosphazenes as minor products, and trans-bis(4-fluorobenzyl) (1b-3b) and trans-bis(4-nitrobenzyl) (4b and 5b) spirocyclotriphosphazenes as major products. The bis(4-fluorobenzyl) spirocyclotriphosphazene (1b) reacted with excess pyrrolidine to give fully substituted (1c) phosphazene. The structures of the new compounds were elucidated by elemental analyses, ESI-MS, FTIR, H-1, C-13, and P-31 NMR techniques. The molecular and crystal structures of 1a, 3b and 6 were identified by single crystal X-ray crystallography. The absolute configurations of 3b and 6 were unambiguously established as SS and R respectively, using X-ray crystallographic data. On the other hand, the interactions of 1b, 1c, 3b-5b and 6 with plasmid DNA indicated that compounds 3b, 4b, and 5b caused a decrease in the mobilities and intensities of form I and form II DNA. Compounds 1b, 1c and 6 caused a double strand break of plasmid DNA. All of the tested compounds inhibited enzyme cleavage indicating compound bindings to the specific G/G and A/A nucleotides.