Abstract
A series of S-alkyl derivatives of 3-(substituted-(1,1′-biphenyl)-3-yl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole-6-thiol (4a–j) were synthesized by conventional and microwave irradiation methods. Microwave method proved to be a rapid and better yield compare to that of conventional method. The synthesized compounds were characterized by 1H NMR, 13C NMR, 19F NMR, IR, LCMS, and elemental spectroscopic analysis. These compounds were screened for their in vitro anticancer activity by MTT assay. Among the tested compounds, the compound 4c was the most promising anticancer agent with IC50 value 12 μM in HT29 cell line.
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Algul O, Meric A, Polat S, Yuksek ND, Serin MS (2009) Comparative studies on conventional and microwave-assisted synthesis of a series of 2,4-di and 2,3,4-trisubstituted benzimidazo[1,2-a]pyrimidines and their antimicrobial activities. Cent Eur J Chem 7(3):337–342
Escalante J, Díaz-Coutiño FD (2009) Synthesis of γ-nitro aliphatic methyl esters via michael additions promoted by microwave irradiation. Molecules 14:1595–1604
Filler R, Kobayashi Y (1982) Biomedicinal aspects of fluorine-chemistry. Kodansha Ltd/Elsevier Biomedical Press, Tokyo/Amsterdam
Holla BS, Poojary KN, Rao BS, Shivananda MK (2002) New bis-aminomer captotrizoles and bis-triazolothiadoiazoles as possible anticancer agents. Eur J Med Chem 37:511–517
Holla BS, Rao BS, Sarojini BK, Akberali PM, Kumari NS (2006) Synthesis and studies on some new fluorine containing tiazolothiadiazines as possible as possible antibacterial, antifungal and anticancer agents. Eur J Med Chem 41:657–663
Husain A, Naseer A (2011) Studies on fused heterocyclic 3,6-disubstituted 1,2,4-triazolo-1,3,4-thiadiazoles: synthesis and biological evaluation. Med Chem Res 20:47–54
Isloor AM, Kalluraya B, Shetty P (2009) Regioselective reaction: synthesis, characterization and pharmacological studies of some new Mannich bases derived from 1,2,4-triazoles. Eur J Med Chem 44:3784–3787
Jyothi CH, Rai SN, Kalluraya B (2007) Environmentally benign synthesis of sydnone containing 1,3,4-thiadiazines under microwave and solvent free conditions. J Chem Sci 119(4):299–302
Kalluraya B, Rao JN, Sujith KV (2008) Microwave assisted one-pot synthesis of some 2,5-disubstituted 1,3,4-oxadiazoles. Indian J Heterocycl Chem 17:359–362
Karthikeyan MS, Holla BS, Kalluraya B, Kumari NS (2007) Biological studies of some 2,4-dichloro 5-fluorophenyl containing triazolothiadiazoles. Monatsh Chem 138:1309–1316
Kavallaris M, Verrills NM, Hill BT (2001) Anticancer therapy with novel tubulin-interacting drugs. Drug Resist Update 4(6):392–401
Mathew V, Keshavayya J, Vaidya VP (2006) Heterocyclic system containing bridgehead nitrogen atom: synthesis and pharmacological activities of some substituted 1,2,4-triazolo[1,3-b]-1,3,4-thiadiazoles. Eur J Med Chem 41:1048–1058
Mathew V, Keshavayya J, Vaidya VP, Giles D (2007) Studies on synthesis and pharmacological activities of 3,6-disubstituted-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazloes and their dihydro analogues. Eur J Med Chem 42:823–840
Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65:55–63
Palekar VS, Damel AJ, Shukla SR (2009) Synthesis and antibacterial activity of some novel bis-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and bis-4-thiazolidinone derivatives from terephthalic dihydrazide. Eur J Med Chem 44:5112–5116
Ramaprasad GC, Kalluraya B, Sunil Kumar B, Ravindra KH (2010) Synthesis and biological property of some novel 1,3,4-oxadiazoles. Eur J Med Chem 45:4587–4593
Ramaprasad GC, Kalluraya Balakrishna, Sunil Kumar B, Sahana Malya (2012) Microwave assisted synthesis of triazolothiadiazole analogues as anticancer and antibacterial agents. Der Pharm Chem 4(3):1026–1032
Ramaprasad GC, Kalluraya Balakrishna, Sunil Kumar B, Malya Sahana (2013) Synthesis of new oxadiazole derivatives as anti-inflammatory, analgesic and antimicrobial agents. Med Chem Res 22:5381–5389
Ramaprsad GC, Kalluraya B, Sunil Kumar B, Sahana Mallya (2012) Synthesis, antibacterial and antifungal activities of some novel 1,3,4-oxadiazole analogues. Int J Pharm Pharm Sci 4(Suppl 4):210–213
Sunil D, Isloor AM, Shetty P (2009) Synthesis, characterization and anticancer activity of 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles on Hep G2 cell lines. Der Pharm Chem 1(2):19–26
Acknowledgments
The authors thank the Head, Syngene International Ltd. for laboratory facilities. The authors are also thankful to Dr. Ashis Baran Mandal, Dr. Sandipan Sarkar, Dr. Sateesh Rai, and Dr. Prashanth Latte for their valuable support. The authors are thankful to Dr. Chandrashekhar, Department of Pharmacology, HSK College of Pharmacy, Belgam for anticancer activities.
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Ramaprasad, G.C., Kalluraya, B. & Sunil Kumar, B. Microwave-assisted synthesis of triazolothiadiazole analogs as anticancer agents. Med Chem Res 23, 3644–3651 (2014). https://doi.org/10.1007/s00044-014-0944-x
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DOI: https://doi.org/10.1007/s00044-014-0944-x