European Journal of Chemistry

Facile synthesis and cytotoxic activity of 3,6-disubstituted 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazoles



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Kaliappan Ilango
Parthiban Valentina

Abstract

Afacile synthesis of 3,6-disubstituted-1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazoles (5a-j) has been achieved by condensing 3-aryl substituted 4-amino-5-mercapto (4H)-1,2,4-triazole (4a-b) with various aromatic acids. The structures of the synthesized compounds were supported by IR, 1H NMR, mass spectral data and elemental analysis The compounds were evaluated for in vitro cytotoxic activity against four human cancer cell lines: two ovarian (PA-1and OAW-42) and two breast (T47D and MCF-7) cell lines using the methyl thiazol tetrazolium assay method. It showed that some of the tested compounds 5a, 5b, 5g and 5f exhibited significant activity against PA-1 cell lines and the compounds 5a and 5e exhibited IC50 of 0.72 µM and 0.65 µM, respectively, against the cell lines of MCF-7, which are close to Doxorubin. After comparing the cytotoxic activity results of compounds 5a-j, it was concluded that the incorporation of triazolo-thiadiazole moiety in aryl propionic acid group gives rise to enhanced anticancer activity. Also, the substitution of chloro group in the aryl ring at the 3rd position was found to enhance their potency.

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Ilango, K.; Valentina, P. Facile Synthesis and Cytotoxic Activity of 3,6-Disubstituted 1,2,4-Triazolo-[3,4-B]-1,3,4-Thiadiazoles. Eur. J. Chem. 2010, 1, 50-53.

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References

[1]. Hill, D. L. Cancer Chemother. Pharmacol. 1980, 4, 215-220.
PMid:7002341

[2]. Nelson, J. A.; Rose, L. M.; Benette, L. Cancer Res. 1977, 37, 182-187.
PMid:187332

[3]. Tsukamoto, K.; Suno, M.; Igarashi, K.; Kozai, Y.; Sugino, Y. Cancer Res. 1975, 35, 2631-2636.
PMid:125625

[4]. Goswami, B. N.; Kattaky, J. C. S.; Baruah, J. N. J. Hetercyclic. Chem. 1984, 21, 1225-1229.
doi:10.1002/jhet.5570210460

[5]. Khan, R. H.; Srivastava, R. A. K.; Rastogi, R. C. Indian J. Pharm. Sciences. 1987, 49(2), 48-51.

[6]. Allen, L. B.; Huffmann, J. H.; Sidwell, R. W. Antimicro. Ag. Chemother. 1973, 3, 534-535.
PMid:4790608    PMCid:444450

[7]. Sabrina, B. F.; Marilia, S. C.; Nubia, B. J. S. B.; Marcelo, S. G.; Marlene, M. C.; Warner, B. K.; Vitro, F. F. Eur. J. Med. Chem. 2007, 42, 1388-1395.
doi:10.1016/j.ejmech.2007.02.020
PMid:17445951

[8]. Hart, C. Am. Chem. Soc. 1999, 2, 20-31.

[9]. David, W. A.; Thomas. L. L., Foye’s Principles of Medicinal Chemistry, Fifth ed., Lippincott Williams & Wilkins. London.

[10]. Karabasanagouda, T.; Adhikari, A. V.; Suchethasettey, N. Eur. J. Med. Chem. 2007, 42, 521-529
doi:10.1016/j.ejmech.2006.10.010
PMid:17156898

[11]. Demirbas, N.; Demibras, A.; Karaoglu, S. A.; Celik, E. Arkivoc. 2005, 1, 75-91.

[12]. Invidiata, F. P.; Simoni, D.; Scintu, F.; Pinna, N. Farmaco. 1996, 51, 659-664.
PMid:8981756

[13]. El Khawass, S. M.; Khalli, M. A.; Hazza, A. A.; Bassiouny, A.; Loutfy, N. F. Farmaco. 1989, 44, 703-709.
PMid:2590368

[14]. Al-Masoudi, N. A.; Al-Soud, Y. A. Nucleos. Nucleot. Nucleic. Acids. 2008, 27, 1034-1044.
doi:10.1080/15257770802271771
PMid:18711666

[15]. Amir, M.; Harish, K.; Javed, S. A. Eur. J. Med. Chem. 2008, 43, 2056-2066.
doi:10.1016/j.ejmech.2007.09.025
PMid:18023930

[16]. Guniz Kuchkguzel, S.; Ilkay, K.; Esra, T.; Selvim, R.; Fikrettin, S.; Medine, G.; Erik, D. C.; Levent, K. Eur. J. Med. Chem. 2007, 42, 893-901.
doi:10.1016/j.ejmech.2006.12.038
PMid:17418454

[17]. Amir, M.; Kumar, H.; Javed, S. A. Bioorg. Med. Chem. Lett. 2007, 17, 4504-4508.
doi:10.1016/j.bmcl.2007.06.003

[18]. Jeffrey, M. E.; Linda, S. A.; Andrew, O. M. Meth. Cell Sci. 2005, 11, 15-17.

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