title: Phosphorus-nitrogen compounds. Part 23: syntheses, structural investigations, biological activities, and DNA interactions of new N/O spirocyclotriphosphazenes.
abstract: The Schiff base compounds (1 and 2) are synthesized by the condensation reactions of 2-furan-2-yl-methylamine with 2-hydroxy-3-methoxy- and 2-hydroxy-5-methoxy-benzaldehydes and reduced with NaBH(4) to give the new N/O-donor-type ligands (3 and 4). The monospirocyclotriphosphazenes containing 1,3,2-oxazaphosphorine rings (5 and 6) are prepared from the reactions of N(3)P(3)Cl(6) with 3 and 4, respectively. The reactions of 5 and 6 with excess pyrrolidine, morpholine, and 1,4-dioxa-8-azaspiro [4,5] decane (DASD) produce tetrapyrrolidino (5a and 6a), morpholino (5b and 6b), and 1,4-dioxa-8-azaspiro [4,5] deca (5c and 6c) spirocyclotriphosphazenes. The structural investigations of the compounds are examined by (1)H, (13)C, (31)P NMR, DEPT, HSQC, and HMBC techniques. The solid-state structures of 5, 5a, and 6 are determined using X-ray crystallography. The compounds 5a, 5b, 5c, 6a, 6b, and 6c are subjected to antimicrobial activity against six patojen bacteria and two yeast strains. In addition, interactions between these compounds and pBR322 plasmid DNA are presented by agarose gel electrophoresis.
authors: Department of Chemistry, Ankara University, 06100 Ankara, Turkey.
authors: Nuran
authors: N
authors: Asmafiliz
authors: Zeynel
authors: Z
authors: Kılıç
authors: Zeliha
authors: Z
authors: Hayvalı
authors: Leyla
authors: L
authors: Açık
authors: Tuncer
authors: T
authors: Hökelek
authors: Hakan
authors: H
authors: Dal
authors: Yağmur
authors: Y
authors: Oner
mesh_terms: D000900:Anti-Bacterial Agents / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D018360:Crystallography, X-Ray; D004247:DNA / Q000378:metabolism*; D004587:Electrophoresis, Agar Gel; D005658:Fungi / Q000187:drug effects; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D009584:Nitrogen / Q000737:chemistry*; D017672:Nitrogen Compounds / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D010100:Oxygen / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D000900:Anti-Bacterial Agents; D017672:Nitrogen Compounds; D009943:Organophosphorus Compounds; D004247:DNA; D009584:Nitrogen; D010100:Oxygen