Synthesis, structural characterization and antimicrobial activities of cyclochlorotriphosphazene derivatives derived from N-(1-Naphthyl)ethylenediamine


TÜRE S., DARCAN C., TÜRKYILMAZ O., Kaygusuz Ö.

Phosphorus, Sulfur and Silicon and the Related Elements, cilt.195, sa.6, ss.507-515, 2020 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 195 Sayı: 6
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1080/10426507.2020.1723096
  • Dergi Adı: Phosphorus, Sulfur and Silicon and the Related Elements
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier
  • Sayfa Sayıları: ss.507-515
  • Anahtar Kelimeler: antimicrobial activity, Candida albicans ATCC 10231, Cyclotriphosphazene, Escherichia coli W3110, N-(1-naphtyl)ethylenediamine
  • Bilecik Şeyh Edebali Üniversitesi Adresli: Evet

Özet

The nucleophilic substitution reactions of cylochlorotriphosphazene (N3P3Cl6) with N-(1-Naphthyl)ethylenediamine resulted in the following formation of partially and fully substituted cyclotriphosphazene derivatives: 2,4,4,6,6-pentachloro-2-open-chain-N-(1-Naphthyl) ethylendiamino-cyclotriphosphazatriene (3); 4,4,6,6-tetrachloro-2,2-spiro-N-(1-Naphthyl) ethylendiamino-cyclotriphosphazatriene (4); 2,6,6-trichloro-2-open-chain-4,4-spiro-N-(1-Naphthyl)ethylendiamino-cyclotriphosphazatriene (5); 2,4-dichloro-2,4-ansa-6,6-spiro-N-(1-Naphthyl)ethylendiamino)-cyclotriphosphazatriene (6); and 2,4,6-trichloro-2,4,6-non-gem-open-chain-N-(1-Naphthyl)ethylendiamino)-cyclotriphosphazatriene (7); 2,2,4,4,6,6-tri-spiro-N-(1-Naphthyl)ethylendiamino)-cyclotriphosphazatriene (8); 2,4-dichloro-2,4-cis-open-chain-6,6-spiro-N-(1-Naphthyl)ethylendiamino)-cyclotriphosphazatriene (9); and 2,4,6,6-tetrachloro -2,4-ansa-N-(1-Naphthyl)ethylendiamino)-cyclotriphosphazatriene (10). The reactions produced the 4,4,6,6-tetrachloro-2,2-spiro-N-(1-Naphthyl) ethylendiamino-cyclotriphosphazatriene (4) and 2,4,6,6-tetrachloro-2,4-ansa-N-(1-Naphthyl)ethylendiamino)-cyclotriphosphazatriene (10) derivatives as the major products in this system. The structures of the compounds were characterized by FT-IR, elemental analysis, TLC-MS, FT-IR, 1H, and 31P NMR spectral data. All the derived compounds (3–10) were screened for antimicrobial activity by using the broth-agar microdilution technique for the determination of MIC and MCC values. In this context, the compounds were examined against three different human pathogens; Escherichia coli W3110, Staphylococcus aureus ATCC 25923 and Candida albicans ATCC 10231. Except compounds 6 and 9, the rest of the compounds exhibited significant antimicrobial activity on E. coli (W3110), S. aureus (ATCC 25923) and C. albicans (ATCC 1023). Among the synthesized derivatives, compound 4 is the most active agent against the referenced bacteria.