ANTIMICROBIAL EVALUATION OF SOME HYDRAZONE DERIVATIVES

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Jankulovska, M.S.
Dimova, V.
Doneva-Sapceska, D.

Abstract

Hydrazone derivatives represent one of the most active classes of compounds possessing a broad spectrum of biological activity. The use of the hydrazones is due to their anti-inflammatory, antimicrobial, antidepressant, antitumoral, analgesic, antiplatelet, anticonvulsant, antischistosomiasis and antiviral activity. Due to their physiological activity, they are also used in agriculture as herbicides, insecticides, fungicides and plant growth regulators. Furthermore, hydrazone derivatives possessing an azomethine proton (-NH-N=CH-) constitute a significant class of compounds for new drug development in order to synthesize effective agents against microbial activity. Considering these applications some psubstituted aromatic hydrazones were previously synthesized and characterized. In this study a series of aromatic hydrazones were evaluated for their in vitro growth and inhibitory activity against Bacillus subtilis, Aspergillus niger and Candida utilis, using filter paper disc method. Stock solutions of compounds were prepared in DMSO, as inert medium in three different concentration levels: 1, 5 and 10 mg/mL. A control disc using DMSO without any test compound was included and there was no inhibitory activity in those disks. The diameter of zone of inhibition (mm) was measured. Every test was done in triplicate to confirm the findings. The screening results indicate that not all investigated compounds exhibited antimicrobial activities. It can be noted that compounds with N-p-methoxy substitute group showed the greatest inhibitory effect against Bacillus subtilis (max zone of inhibition of 14.3 mm) and Candida utilis (max zone of inhibition of 16 mm). All investigated hydrazones showed no inhibitory effects against Aspergillus niger.

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Backes, G. L., Neumann, D. M., Jursic, B. (2014). Synthesis and antifungal activity of substituted salicylaldehyde hydrazones, hydrazides and sulfohydrazides. Bioorganic & Medicinal Chemistry, 22(17): 4629-4636.
Corhnelissen, J. P., Van Diemen, J. H., Groeneveld, L. R,, Haasnoot, J. G., Spek, A. L. (1992). Synthesis of Co(II), Ni(II) and Cu(II) Complexes from Schiff base. Inorganic Chemistry, 31: 198-202.
Darnell, G., Richardson, D. R. (1999). The potential of iron chelators of the pyridoxalisonicotinoyl hydrazone class as effective antiproliferative agents III: the effect of the ligands on molecular targets involved in proliferation. Blood, 94: 781792.
Eissa, H. H. (2015). Synthesis, Characterization, Anticorrosion Activity and Antibacterial Activity of Macrocyclic Schiff Bases Based on 1,3-Dithiocarbonyl Phenyl Dihydrazide, Organic Chemistry: Current Research, 4(4): 151-163.
El-Sabbagh, O. I., Rady, H. M. (2009). Synthesis of new acridines and hydrazones derived from cyclic beta-diketone for cytotoxic and antiviral evaluation. European Journal of Medicinal Chemistry, 44(9): 3680-3686.
El-Sayed, N. N. E., Alafeefy, A. M., Bakht, M. A., Masand, V. H., Aldalbahi A., Chen, N., Fan, C., Bacha, A. B. (2016). Synthesis, Antiphospholipase A2, Antiprotease, Antibacterial Evaluation and Molecular Docking Analysis of Certain Novel Hydrazones. Molecules, 21: 1664.
Jankulovska, M., Colanceska-Ragenovic, K., Dimova, V., Spirevska, I., Makreski, P. (2012). Synthesis and characterization of new p-substituted aromatic hydrazones. Organic Chemistry: An Indian Journal, 8(9): 326-334.
Khan, S. A. (2008). Synthesis, characterization and in vitro antibacterial activity of new steroidal 5-en-3-oxazolo and thiazoloquinoxaline. European Journal of Medicinal Chemistry, 43(9): 2040-2044.
Leboffe, M. J., Pierce, B. E. (2008). Microbiology: Laboratory Theory and Application Brief edition. Morton Publishing Company, U.S.A.
Liu, M., Wang, Y., WangYang, W. Z., Liu, F., Cui, Y. L., Duan, Y. S., Wang, M., Liu, S. Z., Rui, C. H. (2010). Design, synthesis, and insecticidal activities of phthalamides containing a hydrazone substructure. Journal of Agriculture and Food Chemistry, 58: 6858–6863.
Murukan, B., Mohanan, K. (2007). Synthesis, characterization and antibacterial properties of some trivalent metal complexes with [(2-hydroxy-1-naphthaldehyde)3-isatin]-bishydrazone. Journal of Enzyme Inhibition and Medicinal Chemistry, 22(1): 65-70.
Ortiz, S., Nelson, A. R., Kesternich, A. V, Pérez-Fehrmann, A. M., Christenb, A. P., Marcourt, L. B. (2016). Synthesis and antifungal activity of diaryl hydrazones from 2,4-dinitrophenylhydrazine. Journal of Chilean Chemical Society, 61(3): online: ISSN 0717-9707.
Richardson, D. R., Bernhardt, P. V. (1999). Crystal and molecular structure of 2hydroxy-1-naphthaldehyde isonicotinoyl hydrazone (NIH) and its iron(III) complex: an iron chelator with anti-tumour activity. Journal of Biological Inorganic Chemistry, 4(3): 266-273.
Rollas, S., Küçükgüzel, G. Ş. (2007). Biological Activities of Hydrazone Derivatives. Molecules, 12: 1910-1939.
Sclafani, J. A., Maranto, M. T., Sisk, T. M., Van Arman, S. A. (1996). Terminal Alkylation of Linear Polyamines. Journal of Organic Chemistry, 61: 3221-3222.
Secci, D., Bizzarri, B., Bolasco, A., Carradori, S., D'Ascenzio, M., Rivanera, D., Mari, E., Polletta, L., Zicari, A. (2012). Synthesis, anti-Candida activity, and cytotoxicity of new (4-(4-iodophenyl)thiazol-2-yl)hydrazine derivatives. European Journal of Medicinal Chemistry, 53: 246-253.
Singh, M., Raghav, N. (2011). Biological activities of hydrazones: A review. International Journal of Pharmacy and Pharmaceutical Sciences, 3(4): 26-32.
Verma, G., Marella, A., Shaquiquzzaman, M., Akhtar, M., Ali, M. R., Alam, M. M. (2014). A review exploring biological activities of hydrazones. Journal of Pharmacy and Bioallied Science, 6(2): 69–80.
Wu, J., Wang, J., Hu, D., He, M., Jin, L., Song, B. (2012). Synthesis and antifungal activity of novel pyrazolecarboxamide derivatives containing a hydrazone moiety. Chemistry Central Journal, 6: 51.
Yadawe, M. S., Patil, S. A. (1997). Synthesis, characterization and biological studies of cobalt(II) and nickel(II) complexes with new Schiff bases. Transition Metal Chemistry, 22(3): 220-224.