Synthesis, E/Z isomerisation and antimicrobial studies of different structured novel ketone derivatives.

Abstract

In this study five different structured mono ketones’ (k1- k5) novel derivatives as five new   hydrazones (h1-h5) and   five new semicarbazones (s1-s5) were synthesized.  The synthesized compounds were identified by IR, ¹H-NMR, ¹³C-NMR, mass and chromatographic methods for their structures and E/Z isomerizations.  These mentioned hydrazones and semicarbazones were investigated for their antimicrobial activities.  Seven bacterias and three fungis were tested. Ciprofloxacin and Fluconazole were used as standards. MIC values were determined. The relationship between structure and antimicrobial actvity was discussed. Hydrazones were more effective than semicarbazones. Besides, acetyl acetone as a diketone delivered the known 1-(2,4-dinitrophenyl)-3,5-dimethyl-1H-pyrazole (p1) which showed very high antimicrobial activity than hydrazones and semicarbazones against Klebsiella pneumoniae ATCC 4352, Proteus mirabilis ATCC 14153, Staphylococcus epidermidis ATCC 12228, Enterococcus faecalis ATCC 29212, Candida parapsilosis ATCC 22019, Candida tropicalis ATCC 750.

Keywords

• Diazo compounds,Substituent effect,Heterocycles,Antimicrobial activity,Pyrazole

References

1. 1. Reddy KH, Reddy PS, Babu PR, (2000) Nuclease activity of 2-substituted heteroaromatic thiosemicarbazone and semicarbazone copper (II) complexes.Transition Metal Chemistry 25, 154-160.
2. 2. Babahan I, Coban EP, Biyik H, (2013) Synthesis, characterization and antimicrobial activities of vic-dioxime derivatives containing heteroaromatic hydrazine groups and their metal complexes.Maejo International Journal of Science and Technology 7:01, 26-41.
3. 3. Enyedy EA, Bognar GM, Nagy NV, Jakusch T, Kiss T, (2014) Solution speciation of potential anticancer metal complexes of salicylaldehyde semicarbazone and its bromo derivative.Polyhedron 67, 242-252.
4. 4. Kiasat AR, Kazemi F, Mehrjardi MF, (2007) Basic alumina as an efficient catalyst for preparation of semicarbazones in solvent free conditions. Journal of Chinese Chemical Society 54, 1337-1339.
5. 5. Sameem S, Kumar N, Pathak D, (2012) Synthesis and anticonvulsant activity of some newer semicarbazone derivatives. International Journal of Pharmaceutical Sciences and Drug Research 4:3, 195-198.
6. 6. Gup R, (2013), Synthesis and spectroscopic studies of new bis-acylhydrazone compounds. Chimica acta Turcica 35:1, 55-61.
7. 7. Torje IA, Valean AM, Cristea C, (2012) Phenothiazine-carboxaldehyde-hydrazone derivatives, synthesis, characterisation and electronic properties. Academia Romana 57:4-5, 337-344.
8. 8. Hu J, Chen S, Sun Y, Yang J, Rao Y, (2012) Synthesis of tri-and tetrasubstituted pyrazoles via Ru (II) catalysis: Intramolecular aerobic oxidative C-N coupling. Organic Letters 14:19, 5030-5033.

9. 9. Popiolek L, (2017) Hydrazide-hydrazones as potential antimicrobial agents: Overview of the literature since 2010. Medicinal Chemistry Research 26:2, 287-301.
10. 10. Rahmatzadeh SS, Karami B, Khodabakhshi S, (2015) A modified and practical synthetic route to indazoles and pyrazoles using tungstate sulfuric acid. Journal of the Chinese Chemical Society 62, 17-20.
11. 11. Anandarajagopal K, Sunilson JA, Illavarasu A, Thangavelpandian N, Kalijaran R, (2010) Antiepileptic and antimicrobial activities of novel 1-(unsubstituted/substituted)-3,5-dimethyl-1H-pyrazole derivatives. International Journal of ChemTech Research 281, 45-49.
12. 12. Parashar B, Jain A, Bharadwaj S, Sharma VK, (2012) Synthesis and pharmacological properties of some novel pyrazolidine and pyrazole derivatives. Medicinal Chemistry Research 21:8, 1692-1699.
13. 13. Breusch FL, Baykut F, (1953) Darstellung der Di-n-alkyl-ketone mit 15bis 22 C-Atomen (V.Mitteil. über isomere und homologe Reihen)Chemische Berichte 86, 684-688.
14. 14. Clinical and Laboratory Standards Institute, (1997) Reference Method for Broth Dilution Antifungal susceptibility testing of yeasts; Approved Standard- 2rd ed. M 27-A2; CLSI, Wayne, PA.
15. 15. Clinical and Laboratory Standards Institute, (2006) Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically, 7th ed. Approved Standard M7-A7; CLSI, Wayne, PA.