Synthesis and spectroscopic characterization of medicinal azo derivatives and metal complexes of Indandion

Autor: Muhammad Ashfaq, Hafiza Ammara Naseem, Javaria Jamil, M.M. Ahmad, Syed Shoaib Ahmad Shah, Areeba Ashfaq, Habib-ur-Rehman Shah, Sajidah Parveen, Khalil Ahmad, Salma Shaheen
Rok vydání: 2019
Předmět:
Zdroj: Journal of Molecular Structure. 1198:126885
ISSN: 0022-2860
1400-1500
Popis: The development of new and more effective antibiotic agents is necessary for human health. Herein, we have prepared the series of azo-derivatives of 1,3-indandion and metal complexes (Cu2+, Zn2+, Ni2+ and Mn2+) with these azo derivatives like 3-hydroxy-2-[phenyldiazenyl]-1H-inden-1-one (HPDIO), 3-hydroxy-2-[2-methylphenyldiazenyl]-1H-inden-1-one (HMPDIO),3-hydroxy-2-[2-nitrophenyldiazenyl]-1H-inden-1-one (HNPDIO) and 3-hydroxy2-[2-chlorophenyldiazenyl]-1H-inden-1-one (HCPDIO) have been successfully synthesized and screened against some bacteria. The appearance of –N N- peak at 1400-1500 cm−1 with disappearance of NH2 peak at 3500 cm−1 in FTIR spectra and chemical shift at 4.07–4.05 ppm and appearance of multiplet at 8.0–7.5 ppm for phenyl protons confirmed the synthesis of new azo derivatives. The appearance of, C–N sharp peak at 102 ppm, aromatic carbon peak in the range of 115–135 ppm, C–OH sharp peak at 192 ppm and C O peaks at 160–187 ppm and appearance of molecular ion peaks at 250 m/z, 264 m/z, 295 m/z and 284 m/z respectively further gives strong indication for the synthesis of proposed azo derivatives. Further, the XRD analysis of azo derivatives confirmed that these derivatives have cubic geometry. A relationship between anti-bacterial activities and structure of synthesized compounds have been established, the addition of electron donating group (for example methyl group) on the compound (HMPDIO) showed remarkable results which were equal to standard drug ciproxin against B. subtilis. Furthermore, the metal complexes of HCPDIO with Zn(II) and HNPDIO with Cu(II) showed more anti-bacterial activity against E.coli, P.aeruginose, B.subtilis and S.aureus than other metal complexes and azo derivatives. The compounds also screened against antioxidant as well as chymotrypsin activity and HCPDIO gives maximum inhibition against antioxidant activity than standard drug (BHA). All the ligands give good inhibition results against chymotrypsin activity except HCPDIO.
Databáze: OpenAIRE
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