Keywords
thiosemicarbazones
antimicrobial
antifungal
anticancer
How to Cite
Abstract
Arylalkylidene derivatives of aminotriazoles (3a-3j) were synthesized and tested for their antimicrobial and anticancer activity. Four non-pathogenic bacteria [E. coli (NCIM 2068), K. pneumoniae (NCIM 2957), S. aureus (NCIM 2079), B. subtilis (NCIM 2921)] two fungi [C. albicans, A. niger] and two cancer cell lines [HBL-100 and HT-29] were employed in the study. All the compounds were found to have better antibacterial activity against B. subtilis than Ciprofloxacin (standard) and compound 3i was equivalent to Ciprofloxacin in inhibiting S. aureas. Similarly all the compounds inhibited the growth of A. niger better than Fluconazole and compound 3c was equivalent to Fluconazole (standard) in inhibiting C. albicans. In case of anticancer activity none of the molecule exhibited activity better than the standard used (Methotrexate), though they have inhibitory concentration at submicromolar level.References
WHO, Containing antimicrobial resistance: review of the literature and report of a WHO Workshop on the Development of a Global Strategy for the Containment of Antimicrobial Resistance, Geneva, Switzerland, 4-5 February; 1999.
El-Sharief, M. A.; Abbas, S. Y.; El-Bayouki, K. A.; El-Gammal, E. W., Synthesis of thiosemicarbazones derived from N-(4-hippuric acid)thiosemicarbazide and different carbonyl compounds as antimicrobial agents. Eur J Med Chem 2013, 67, 263-8. http://dx.doi.org/10.1016/j.ejmech.2013.06.031
Mohamed, N. A.; Mohamed, R. R.; Seoudi, R. S., Synthesis and characterization of some novel antimicrobial thiosemicarbazone O-carboxymethyl chitosan derivatives. Int J Biol Macromol 2014, 63, 163-9. http://dx.doi.org/10.1016/j.ijbiomac.2013.10.044
Rollas, S.; Kkgzel, S. G., Biological activities of hydrazone derivatives. Molecules 2007, 12, 1910-39. http://dx.doi.org/10.3390/12081910
Mashayekhi, V.; Haj Mohammad Ebrahim Tehrani, K.; Azerang, P.; Sardari, S.; Kobarfard, F., Synthesis, antimycobacterial and anticancer activity of novel indole-based thiosemicarbazones. Arch Pharm Res 2013. http://dx.doi.org/10.1007/s12272-013-0242-z
Liu, M. C.; Lin, T. S.; Sartorelli, A. C., 1 Chemical and Biological Properties of Cytotoxic ?-(N)-Heterocyclic Carboxaldehyde Thiosemicarbazones. Prog Med Chem 1995, 32, 1-35. http://dx.doi.org/10.1016/S0079-6468(08)70451-X
Alvero, A. B.; Chen, W.; Sartorelli, A. C.; Schwartz, P.; Rutherford, T.; Mor, G., Triapine (3-aminopyridine-2-carboxaldehyde thiosemicarbazone) induces apoptosis in ovarian cancer cells. J Soc Gynecol Investig 2006, 13, 145-52. http://dx.doi.org/10.1016/j.jsgi.2005.11.004
Finch, R. A.; Liu, M. C.; Cory, A. H.; Cory, J. G.; Sartorelli, A. C., Triapine (3-aminopyridine-2-carboxaldehyde thiosemicarbazone; 3-AP): an inhibitor of ribonucleotide reductase with antineoplastic activity. Adv Enzyme Regul 1999, 39, 3-12. http://dx.doi.org/10.1016/S0065-2571(98)00017-X
Finch, R. A.; Liu, M.; Grill, S. P.; Rose, W. C.; Loomis, R.; Vasquez, K. M.; Cheng, Y.; Sartorelli, A. C., Triapine (3-aminopyridine-2-carboxaldehyde- thiosemicarbazone): A potent inhibitor of ribonucleotide reductase activity with broad spectrum antitumor activity. Biochem Pharmacol 2000, 59, 983-91. http://dx.doi.org/10.1016/S0006-2952(99)00419-0
Chetan, B.; Bunha, M.; Jagrat, M.; Sinha, B. N.; Saiko, P.; Graser, G.; Szekeres, T.; Raman, G.; Rajendran, P.; Moorthy, D.; Basu, A.; Jayaprakash, V., Design, synthesis and anticancer activity of piperazine hydroxamates and their histone deacetylase (HDAC) inhibitory activity. Bioorg Med Chem Lett 2010, 20, 3906-10. http://dx.doi.org/10.1016/j.bmcl.2010.05.020
Krishnan, K.; Prathiba, K.; Jayaprakash, V.; Basu, A.; Mishra, N.; Zhou, B.; Hu, S.; Yen, Y., Synthesis and Ribonucleotide reductase inhibitory activity of thiosemicarbazones. Bioorg Med Chem Lett 2008, 18, 6248-50. http://dx.doi.org/10.1016/j.bmcl.2008.09.097
Kulandaivelu, U.; Padmini, V. G.; Suneetha, K.; Shireesha, B.; Vidyasagar, J. V.; Rao, T. R.; K N, J.; Basu, A.; Jayaprakash, V., Synthesis, antimicrobial and anticancer activity of new thiosemicarbazone derivatives. Arch Pharm (Weinheim) 2011, 344, 84-90. http://dx.doi.org/10.1002/ardp.201000201
Ali, A. Q.; Teoh, S. G.; Salhin, A.; Eltayeb, N. E.; Khadeer Ahamed, M. B.; Majid, A. M., Synthesis of isatin thiosemicarbazones derivatives: In vitro anti-cancer, DNA binding and cleavage activities. Spectrochim Acta A Mol Biomol Spectrosc 2014, 125, 440-8. http://dx.doi.org/10.1016/j.saa.2014.01.086
Klayman, D. L.; Bartosevich, J. F.; Griffin, T. S.; Mason, C. J.; Scovill, J. P., 2-Acetylpyridine thiosemicarbazones. 1. A new class of potential antimalarial agents. J Med Chem 1979, 22, 855-62. http://dx.doi.org/10.1021/jm00193a020
Barry, A., Procedure for testing antimicrobial agents in agar media: Theoretical considerations. Antibiotics in Laboratory Medicine. Edition 1986, 2, 1-26.
Grever, M. R.; Schepartz, S.; Chabner, B. In The National Cancer Institute: Cancer Drug Discovery and Development Program, 1992; p 622.
Boyd, M. R.; Paull, K. D., Some practical considerations and applications of the National Cancer Institute in vitro anticancer drug discovery screen. Drug Develop Res 1995, 34, 91-109. http://dx.doi.org/10.1002/ddr.430340203
Monks, A.; Scudiero, D.; Skehan, P.; Shoemaker, R.; Paull, K.; Vistica, D.; Hose, C.; Langley, J.; Cronise, P.; Vaigro-Wolff, A., Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. J Natl Cancer Inst 1991, 83, 757-66. http://dx.doi.org/10.1093/jnci/83.11.757
Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.