ABSTRACT
A series of 6-thiocyanatopurine derivatives introduced with different alkyl groups in position 9 was synthesized. The structures of the synthesized compounds were evaluated via spectroscopic methods and elemental methods of analyses. All the synthesized compounds were screened for their antibacterial activities against Gram-positive and Gram-negative bacteria and for their antifungal activities against yeast strains. All the synthesized compounds showed better antibacterial activities against Gram-positive bacteria compared to Gram-negative bacteria. DNA interactions with pBR322 DNA were determined. Most of the compounds caused conformational changes in DNA.
Subject(s)
Anti-Bacterial Agents/chemical synthesis , Antifungal Agents/chemical synthesis , DNA/metabolism , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Antifungal Agents/chemistry , Antifungal Agents/pharmacology , DNA/chemistry , Gram-Negative Bacteria/drug effects , Gram-Positive Bacteria/drug effects , Plasmids/chemistry , Plasmids/metabolismABSTRACT
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.
