Phosphorus-nitrogen compounds. Part 40. The syntheses of (4-fluorobenzyl) pendant armed cyclotetraphosphazene derivatives: Spectroscopic, crystallographic and stereogenic properties, DNA interactions and antimicrobial activities


ELMAS G., OKUMUŞ A., Kilic Z., Cam M., AÇIK L., HÖKELEK T.

INORGANICA CHIMICA ACTA, cilt.476, ss.110-122, 2018 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 476
  • Basım Tarihi: 2018
  • Doi Numarası: 10.1016/j.ica.2018.02.025
  • Dergi Adı: INORGANICA CHIMICA ACTA
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.110-122
  • Anahtar Kelimeler: (4-Fluorobenzyl)cyclotetraphosphazenes, Spectroscopy, Crystallography, Stereogenism, DNA cleavage, Antimicrobial activity, BIOLOGICAL-ACTIVITIES, CRYSTAL-STRUCTURES, STRUCTURAL CHARACTERIZATIONS, STEREOCHEMICAL ASPECTS, CYTOTOXIC ACTIVITIES, CHIRAL PHOSPHAZENES, SPIRO, OCTACHLOROCYCLOTETRAPHOSPHAZENE, CYCLOTRIPHOSPHAZENES, ANTITUBERCULOSIS
  • Ankara Üniversitesi Adresli: Evet

Özet

The Cl substitution reaction of octachlorocyclotetraphosphazene, N4P4Cl8 (1), with 1.2 equimolar amounts of sodium salt of N/O donor-type bidentate ligand (2) gave four different new (4-fluorobenzyl) pendant armed cyclotetraphosphazene derivatives; namely, mono-(4-fluorobenzyl)-spiro- (spiro; 3), mono-(4-fluorobenzyl)-2-cis-4-dichloro-ansa- (2,4-ansa; 4), bis-(4-fluorobenzyl)-2-trans-6-dispiro (5) and bis-(4-fluorobenzyl)-2-trans-4-dispiro (6) cyclotetraphosphazenes of which 3 was the major product (yield 55%). Compound 3 was treated with mono and difunctional reagents to prepare the fully substituted products (3a-3j) due to its very high yield. However, tetrapyrrolidino-2-cis-4-dichloro-ansa- product (4a) was obtained from the reaction of 2,4-ansa (4) with excess pyrrolidine. The new cyclotetraphosphazenes were characterized by elemental analyses, mass spectrometry (ESI-MS), Fourier transform infrared (FTIR), H-1, C-13, and P-31 NMR techniques. The structures of 3 and 3g were determined by X-ray crystallography. 2,4-Ansa compounds (4 and 4a) have two stereogenic P atoms. The stereogenic property of 4 was identified by P-31 NMR spectra in the addition of the chiral solvating agent, (R)-(+)-2,2,2-trifluoro-1-(9'-anthryl)-ethanol (CSA). The tetraspiro compounds (3i and 3j) look similar to a propeller, and they may have P and Matropisomers. The antimicrobial activities of the compounds were screened against some G(-)/G(+) bacteria and yeast strains. The interactions of the compounds with supercoiled plasmid pBR322 DNA and their inhibited DNA restriction were examined. (C) 2018 Elsevier B.V. All rights reserved.