Share This Article:

Synthesis, Characterization and Antibacterial Activity of Biologically Important Vanillin Related Hydrazone Derivatives

Abstract Full-Text HTML Download Download as PDF (Size:192KB) PP. 71-77
DOI: 10.4236/ijoc.2011.13012    12,072 Downloads   29,912 Views   Citations


Hydrazone derivatives of vanillin are found to possess anti-bacterial activities. Based on higher bio-activity of hydrazones, new hydrazone derivatives were synthesized from Piperdine-4-carboxylicacid methyl ester (1). The compounds 1-pyrimidine-2-yl piperidine-4-carboxylicacid(4-hydroxy-3-methoxy benzylidine)-hy- drazide (10), 1-pyrimidine-2-yl piperidine-4-carboxylicacid (3,4-dimethoxy benzylidine) hydrazide (11), 1-pyrimidine-2-yl piperidine-4-carboxylicacid(4-butoxy-3-methoxy benzylidine)-hydrazide (12), 1-pyr- imidine-2-yl piperidine-4-carboxylicacid(3-methoxy-4(2-methoxy ethoxy) benzylidine)-hydrazide (13) were synthesized, purified and characterized by 1HNMR, 13CNMR, LCMS, FT-IR and HPLC techniques. The synthesized hydrazone derivatives were further checked for anti-bacterial activities by paper disc diffusion method against Pseudomonas aeruginosa and Staphylococcus aureus bacterial strains.

Conflicts of Interest

The authors declare no conflicts of interest.

Cite this paper

T. Govindasami, A. Pandey, N. Palanivelu and A. Pandey, "Synthesis, Characterization and Antibacterial Activity of Biologically Important Vanillin Related Hydrazone Derivatives," International Journal of Organic Chemistry, Vol. 1 No. 3, 2011, pp. 71-77. doi: 10.4236/ijoc.2011.13012.


[1] S. Riva and L. G. Silvestri, “Rifamycine: A General view,” Annual Review of Microbiology, Vol. 26, 1972, pp. 199-224. doi:10.1146/annurev.mi.26.100172.001215
[2] V. I. Yudelevich, V. V. Belakhov, E. V. Komarov, B. I. Ionin, G. L. Myasnikova, M. S. Polyak, M. A. Shneider and L. A. Rachkovskaya, “Synthesis and Biological Activity of New Derivatives of 1,2,3,4-Tetrahydroquina- zolin-4-One,” Pharmaceutical Chemistry Journal, Vol. 18, No. 10, 1984, pp. 704-707. doi:10.1007/BF00773018
[3] S. Rollas and S. G. Kucukguzel, “Biological Activities of Hydrazone Derivatives,” Molecules, Vol. 12, No. 8, 2007, pp. 1910-1939.
[4] O. A. Olayinka, A. O. Craig, C. N. Obinna and A. A. David, “Microwave Assisted Synthesis and Antimicrobial Activity of 2-Quinoxalinone-3-Hydra-Zone Derivatives,” Bioorganic & Medicinal Chemistry, Vol. 18, No. 1, 2010, pp. 214-221. doi:10.1016/j.bmc.2009.10.064
[5] S. Rollas, N. Gulerman and H. Edeniz, “Synthesis and Antimicrobial Activity of Some New Hydrazones of 4-Fluorobenzoic Acid Hydrazide and 3-Acetyl-2,5-Dis- ubstituted-1,3,4-Oxadiazolines,” IL Farmaco, Vol. 57, No. 2,. 2002, pp. 171-174.
[6] A. Cukurovali, B. Yilmaz, S. Gur and C. Kazaz, “Syn- thesis, Antibacterial and Antifungal Activity of Some New Thiazolylhydrazone Derivatives Containing 3-Sub- stituted Cyclobutane Ring,” European Journal of Medi- cinal Chemistry, Vol. 41, No. 2, 2006, pp. 201-207. doi:10.1016/j.ejmech.2005.01.013
[7] J. Capilla, C. Serena, F. Javier, T. Ortoneda and J. Guarro, “Efficacy of Voriconazole in Treatment of Systemic Sce- dosporiosis in Neutropenic Mice,” Antimicrobial Agents Chemother, Vol. 47, No. 12, 2003, pp. 3976-3978. doi:10.1128/AAC.47.12.3976-3978.2003
[8] M. G. Mamolo, V. Falagiani, D. Zampieri, U. Vio, E. Banfi and G. Scialino, “Synthesis and Antimycobacterial Activity of (3,4-Diaryl-3H-Thiazol-2-Ylidene)-Hydrazide Derivatives,” IL Farmaco, Vol. 58, No. 9, 2003, pp. 631- 637.
[9] J. R. Dimmock, S. C. Vasishtha and J. P. Stables, “anticonvulsant Properties of Various Acetylhydrazones, Oxamoylhydrazones and Semicarbazones Derived from Aromatic and Unsaturated Carbonyl Compounds,” European Journal of Medicinal Chemistry, Vol. 35, No. 2, pp. 241-248.
[10] P. C. Lima, L. M. Lima, K. C. Silva, P. H. Leda, A. L. P. Miranda, C. A. M. Fraga, and E. J. Barreiro, “Synthesis and Analgesic Activity of Novel N-Acylarylhydrazones and Isosters, Derived from Natural Safrole,” European Journal of Medicinal Chemistry, Vol. 35, No. 2, 2000, pp. 187-203. doi:10.1016/S0223-5234(00)00120-3
[11] G. U. Salgin, K. N. Gokham, O. Gostal, Y. Koysal, E. Kilici, S. Isik, G. Aktay and M. Ozalp, “1-Acylthiose- micarbazides, 1,2,4-Triazole-5(4H)-Thiones, 1,3,4-Thia- diazoles and Hydrazones Containing 5-Methyl-2-Benzo- xazolinones: Synthesis, Analgesic-Anti-Inflammatory and Antimicrobial Activities,” Bioorganic & Medicinal Che- mistry, Vol. 15, No. 17, 2007, pp. 5738-5751. doi:10.1016/j.bmc.2007.06.006
[12] A. R. Todeschini, A. L. Miranda, C. M. Silva, S. C. Parrini and E. J. Barreiro, “Synthesis and Evaluation of Analgesic, Anti-Inflammatory and Antiplatelet Properties of New 2-Pyridylarylhydrazone Derivatives,” European Jour- nal of Medicinal Chemistry, Vol. 33, No. 3, 1998, pp. 189-199. doi:10.1016/S0223-5234(98)80008-1
[13] G. A. Silva, L. M. M. Costa, F. C. B. Brito, A. L. P Miranda, E. J. Barreiro and C. A. M. Fraga, “New Class of Potent Antinociceptive and Antiplatelet 10H-Pheno- thiazine-1-Acylhydrazone Derivatives,” Bioorganic & Medicinal Chemistry, Vol. 12, No. 12, 2004, pp. 3149- 3158. doi:10.1016/j.bmc.2004.04.009
[14] A. Imramovsky, S. Polanc, J. Vinsova, M. Kocevar, J. Jampitek, Z. Reckova and J. A. Kaustova, “A New Modification of Anti-Tubercular Active Molecules,” Bioor- ganic & Medicinal Chemistry, Vol. 15, No. 7, 2007, pp. 2551-2559. doi:10.1016/j.bmc.2007.01.051
[15] Y. Janin, “Antituberculosis Drugs: Ten Years of Research,” Bioorganic & Medicinal Chemistry, Vol. 15, No. 7, 2007, pp. 2479-2513. doi:10.1016/j.bmc.2007.01.030
[16] L. C. du Toit, V. Pillay and M. P. Danckwerts, “Tuber- culosis Chemotherapy: Current Drug Delivery Approa- ches,” Respiratory Research, Vol. 7, 2006, p. 118. doi:10.1186/1465-9921-7-118
[17] L. Savini, L. Chiasserini, V. Travagli, C. Pellerano, E. Novellino, S. Consentino and M. B. Pisano, “New α-(N)- Heterocyclichydrazones: Evaluation of Anticancer, Anti- HIV and Antimicrobial Activity,” European Journal of Medicinal Chemistry, Vol. 39, No. 2, 2004, pp. 113- 122. doi:10.1016/j.ejmech.2003.09.012
[18] A. M. El-Hawash, W. A. E Abdel and M. A. El-Dewellawy, “Cyanoacetic Acid Hydrazones of 3-(and 4-)Acetylpyridine and Some Derived Ring Systems as Potential Antitumor and Anti-HCV Agents,” Archiv der Pharmazie, Vol. 339, No. 1, 2006, pp. 14-23. doi:10.1002/ardp.200500161
[19] M. T. Cocco, C. Congiu, V. Lilliu and V. Onnis, “Synthesis and in Vitro Antitumoral Activity of New Hydrazinopyrimidine-5-Carbonitrile Derivatives,” Bioorga- nic & Medicinal Chemistry, Vol. 14, No. 2, 2006, pp. 366-372. doi:10.1016/j.bmc.2005.08.012
[20] S. G. Kucukguzel, A. Mazi, F. Sahin, S. Ozturk and J. Stables, “Synthesis and Biological Activities of Diflunisal Hydrazide-Hydrazones,” European Journal of Medicinal Chemistry, Vol. 38, No. 11-12, 2003, pp. 1005-1013. doi:10.1016/j.ejmech.2003.08.004
[21] V. Sridharan, P. T. Perumal, C. Avendano and J. C. Menendez, “The first aza Diels-Alder Reaction Involving an α,β-Unsaturated Hydrazone as the Dienophile: Stereoselective Synthesis of C-4 Functionalized 1,2,3,4-Tetra- hydroquinolines Containing a Quaternary Stereocenter,” Organic & Biomolecular Chemistry, Vol. 5, 2007, pp. 1351-1353. doi:10.1039/b703083e
[22] A. Espinel-Ingroff, “Standardized Disk Diffusion Method for Yeasts,” Clinical Microbiology Newsletter, Vol. 29, No. 13, 2007, pp. 97-100. doi:10.1016/j.clinmicnews.2007.06.001
[23] W. L. F Armarego and C. L. L. Chai, “Purification of Laboratory Chemicals,” 5th Edition, Amsterdam, Elsevier, 2003.
[24] A. R. Katritzky, H.-Y. He, Q. H. Long and A. L. Wilcoxb, “Preparation of 2,6-Dialkoxybenzaldehydes,” ARKIVOC, Vol. 3, 2001, pp. 3-12.
[25] F. S. Pashkovskii, E. M. Shchukina, M. G. Gribovskii and F. A. Lakhvich, “Heterocyclic Analogs of Prostaglandins: IV. Synthesis of 3,7-Interphenylene 3,10(11) -Dioxa-13- Azaprostanoids and 9-Oxa-7-Azaprostanoids Based on Tetronic Acid and Aromatic Aldehydes,” Russian Journal of Organic Chemistry, Vol. 44, No. 5, 2008, pp. 657-670. doi:10.1134/S1070428008050047

comments powered by Disqus

Copyright © 2018 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.