European Journal of Chemistry 2010, 1(1), 50-53. doi:10.5155/eurjchem.1.1.50-53.4

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


Kaliappan Ilango (1,*) , Parthiban Valentina (2)

(1) Department of Pharmaceutical Chemistry, College of Pharmacy, Sri Ramasamy Memorial University, Kattankulathu, TN-603203, India.
(2) Department of Pharmaceutical Chemistry, College of Pharmacy, Sri Ramasamy Memorial University, Kattankulathu, TN-603203, India.
(*) Corresponding Author

Received: 24 Mar 2010, Accepted: 24 Mar 2010, Published: 31 Mar 2010

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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Keywords


Triazole; Thiadiazole; Triazolo-[3,4-b]-1,3,4-thiadiazoles; Cytotoxic

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DOI: 10.5155/eurjchem.1.1.50-53.4

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Citations

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[1]. Saghir Abbas, Sumera Zaib, Shafiq Ur Rahman, Saqib Ali, Shahid Hameed, Muhammad N. Tahir, Khurram S. Munawar, Farzana Shaheen, Syed M. Abbas, Jamshed Iqbal
Carbonic Anhydrase Inhibitory Potential of 1,2,4-triazole-3-thione Derivatives of Flurbiprofen, Ibuprofen and 4-tert-butylbenzoic Hydrazide: Design, Synthesis, Characterization, Biochemical Evaluation, Molecular Docking and Dynamic Simulation Studies
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[2]. Sattar Ebrahimi
Synthesis of some pyridyl and cyclohexyl substituted 1,2,4 triazole, 1,3,4-thiadiazole and 1,3,4-oxadiazole derivatives
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[3]. Georgios Charitos, Dimitrios T. Trafalis, Panayiotis Dalezis, Constantinos Potamitis, Vasiliki Sarli, Panagiotis Zoumpoulakis, Charalambos Camoutsis
Synthesis and anticancer activity of novel 3,6-disubstituted 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole derivatives
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[4]. A. S. Avakyan, S. O. Vartanyan, A. B. Sargsyan
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[5]. Pooja R. Kamath, Dhanya Sunil, Shubhankar Das, Abdul Ajees Abdul Salam, B.S. Satish Rao
Efficient T3P ® mediated synthesis, differential cytotoxicity and apoptosis induction by indolo-triazolo-thiadiazoles in human breast adenocarcinoma cells
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[6]. Parthiban Valentina, Kaliappan Ilango, Muthu K. Kathiravan
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[7]. Gülsüm Gündoğdu, Sevim Peri Aytaç, Melanie Müller, Birsen Tozkoparan, Filiz Betül Kaynak
Structure determination of two structural analogs, named 3-[1-(2-fluoro-4-biphenyl)ethyl]-6-(4-fluorophenyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole (C23H16F2N4S) and 3-[1-(2-fluoro-4-biphenyl)ethyl]-6-(4-chlorophenyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole (C23H16ClFN4S) by synchrotron X-ray powder diffraction
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How to cite


Ilango, K.; Valentina, P. Eur. J. Chem. 2010, 1(1), 50-53. doi:10.5155/eurjchem.1.1.50-53.4
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(1), 50-53. doi:10.5155/eurjchem.1.1.50-53.4
Ilango, K., & Valentina, P. (2010). Facile synthesis and cytotoxic activity of 3,6-disubstituted 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazoles. European Journal of Chemistry, 1(1), 50-53. doi:10.5155/eurjchem.1.1.50-53.4
Ilango, Kaliappan, & Parthiban Valentina. "Facile synthesis and cytotoxic activity of 3,6-disubstituted 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazoles." European Journal of Chemistry [Online], 1.1 (2010): 50-53. Web. 22 Sep. 2019
Ilango, Kaliappan, AND Valentina, Parthiban. "Facile synthesis and cytotoxic activity of 3,6-disubstituted 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazoles" European Journal of Chemistry [Online], Volume 1 Number 1 (31 March 2010)

DOI Link: https://doi.org/10.5155/eurjchem.1.1.50-53.4

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