Rational synthesis, biological screening of azo derivatives of chloro-phenylcarbonyl diazenyl hydroxy dipyrimidines/thioxotetrahydropyrimidines and their metal complexes

Abstract

Herein, a new series of azo ligands HL-1 (5-(2-chloro-6-(phenylcarbonyl)phenyl)diazenyl)-6-hydroxydihydropyrimidines-2,4dione), HL-2 (5-(2-chloro-6-(phenylcarbonyl)phenyl)diazenyl)-6-hydroxy-2-thioxottetrahydropyrimidin-4one), HL-3 (5-(2,4-dichloro-6-(phenylcarbonyl)phenyl) diazenyl)-6-hydroxydihydropyrimidines-2,4dione), HL-4 (5-(2,4-dichloro-6-(phenylcarbonyl) phenyl)diazenyl)-6-hydroxy-2-thioxotetrahydropyrimidin-4one) and their metal complexes with Cu(II) & Ni(II) were synthesized successfully having excellent yield, in reproducible conditions and for structure elucidation different advance spectroscopic techniques (FTIR, 1H NMR, 13C NMR and Mass Spectrometry) were applied. In FTIR analysis, the absence of peak at 3450-3550 cm-1 due to –NH2 and presence of a new peak of N=N at 1390-1520 cm−1 confirmed synthesis of the ligands. The 1H NMR spectra of azo ligands showed singlet peak at 11.5–13.5 ppm (Ar-OH) for hydroxyl group and –NH2 signals disappearance of anilines at 4–5 ppm also gives strong indication for the synthesis of azo compounds. On complexation two most important peaks (M-O, M-N) appeared in all the metal chelates in the range of 400–600 cm−1 which were not present in any of the ligands, confirmed the formation of complexes. Molecular ion peaks in mass spectra at 273, 388, 407 and 423 m/z value for ligands as well as for complexes at 803, 835, 871 and 904 m/z also give strong indication that proposed ligands and their metal complexes are produced successfully. Biological screening of the synthesized compounds were also carried out against different bacterial strains (E.coli, S.typhi, and B.subtilis), antifungal (C.albicans, A.niger, and C.glabrata) strains and antioxidant activity. From results it was observed that HL-4 and Cu complexes exhibited maximum inhibition against all bacterial and fungal strains as compared to other ligands and standard drug.