PL EN


Preferences help
enabled [disable] Abstract
Number of results
2019 | 126 | 291-298
Article title

Synthesis, characterization and biological property of 3-(5-bromothiophen-2-yl)-6-phenyl-1,7a-dihydro-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives

Content
Title variants
Languages of publication
EN
Abstracts
EN
A library of novel 3-(5-bromothiophen-2-yl)-6-phenyl-1,7a-dihydro-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole were synthesized in excellent yields via domino one-pot two component reactions of 4-amino-3-(5-bromothiophen-2-yl)-4,5-dihydro-1H-1,2,4-triazole-5-thiol and benzoic acid derivatives respectively. A triazolo-thiadiazole system may be viewed as a cyclic analogue of two very important components - thiosemicarbazide and biguanide which often display diverse biological activities. The significant advantages of this reaction include one-pot process, simple work-up procedure, excellent yields and no column chromatographic purification. All intermediates and final compounds were confirmed by 1H NMR, 13C NMR, Mass Spectroscopy methods and IR analysis.
Keywords
Year
Volume
126
Pages
291-298
Physical description
Contributors
  • Chemical Research Laboratory Shree U.P.E.T Mahila Sci. College Dhrol, Gujarat, India
  • Department of Chemistry, M. M. Science College Morbi, Gujarat, India
References
  • [1] Demirbas, N.; Karaoglu, S.A.; Demirbas, A.; Sancak, K. Synthesis and antimicrobial activities of some new 1-(5-phenylamino-[1,3,4]thiadiazol-2-yl)methyl-5-oxo-[1,2,4] triazole and 1-(4-phenyl-5-thioxo-[1,2,4]triazole-3-yl)methyl-5-oxo[1,2,4]triazole derivatives. Eur. J. Med. Chem. 2004, 39, 793-804
  • [2] Mathew, V.; Keshavayya, J.; Vaidya, V.P.; Giles, D. Studies on synthesis and pharmacological activities of 3,6-disubstituted-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and their dihydro analogues. Eur. J. Med. Chem., 2007, 42, 823-840
  • [3] Shamsuzzaman, Siddiqui, T., Alam, M.G. Synthesis of substituted steroidal thiadiazole, triazole and oxidotriazole. Indian J. Chem., 2007, 46B, 2068-2070
  • [4] Swamy, S.N.; Basappa, Priya, B.S.; Prabhuswamy, B.; Doreswamy, B.H.; Prasad, J.S.; Rangappa, K.S. Synthesis of pharmaceutically important condensed heterocyclic 4,6-disubstituted-1,2,4-triazolo-1,3,4-thiadiazole derivatives as antimicrobials. Eur. J. Med. Chem. 2006, 41, 531-538
  • [5] Vikrant, S.P.; Amey, J.D.; Shukla, S.R. 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. 2009, 44, 5112-5116
  • [6] Udupi, R.H.; Setty, S.R.; Srinivasulu, N.; Pasha, T.Y.; Agarwal, N. Heterocyclic systems containing bridgehead nitrogen atom: Synthesis and biological activity of s-triazolo[3,4-b][1,3,4]thiadiazoles. Indian J. Het. Chem. 2003, 12, 361-364
  • [7] Ibrahim, D.A. Synthesis and biological evaluation of 3,6-disubstituted[1,2,4]triazolo [3,4-b][1,3,4]thiadiazole derivatives as a novel class of potential anti-tumor agents. Eur. J. Med. Chem. 2009, 44, 2776-2781
  • [8] Holla, B.S.; Poojary, K.N.; Rao, B.S.; Shivananda, M.K. New bis-amino mercapto triazole and bis-triazolothiadiazoles as possible anticancer agents. Eur. J. Med. Chem. 2002, 37, 511-517
  • [9] Padmavathi, V.; Reddy, G.S.; Padmaja, A.; Kondaiah, P.; Ali-Shazia. Synthesis, antimicrobial and cytotoxic activities of 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazoles. Eur. J. Med. Chem. 2009, 44, 2106-2112
  • [10] Amir, M.; Kumar, A.; Ali, I.; Khan, S.A. Synthesis of pharmaceutically important 1,2,3-thiadiazole and imidazolinone derivatives as antimicrobials. Indian J. Chem. 2009, 48B, 1288-1293
  • [11] Desai, N.C.; Bhavsar, A.M.; Shah, M.D.; Saxena, A.K. Synthesis and QSAR studies of thiosemicarbazides, 1,2,4-triazoles, 1,3,4-thiadiazoles and 1,3,4-oxadiazoles derivatives as potential antibacterial agents. Indian J. Chem. 2008, 47B, 579-589
  • [12] Kamotra, P.; Gupta, A.K.; Gupta, R.; Somal, P.; Singh, S. Microwave assisted synthesis and biological activity of 3- alkyl/aryl-6-(1-chloro-3,4-dihydronaphth-2-yl)-5,6-dihydro-s-triazolo[3,4-b][1,3,4]thiadiazoles. Indian J. Chem., 2007, 46B, 980-984.
  • [13] Mosmann, T.J. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxic assays. J. Immunol. Methods, 1983, 65, 55-63
  • [14] Kavitha, C.V.; Mridula, N.; Ananda Kumar, C.S.; Bibha, C.; Muniappa, K.; Rangappa, K.S.; Sathees, C.R. Novel derivatives of spirohydantoin induce growth inhibition followed by apoptosis in leukemia cells. Biochem. Pharmacol. 2009, 77, 348-363
  • [15] Kishore, K.C.; Vijayalakshmi, K.; Bibha, C.; Mridula, N.; Rama, G.G.; Sathees, C.R. Methyl angolensate, a natural tetranortriterpenoid induces intrinsic apoptotic pathway in leukemic cells. FEBS Lett. 2008, 582, 4066-4076
  • [16] Camille, G.M. The Practice of Medicinal Chemistry. 3rd Ed., 2009, Elsevier, Noida, India.
  • [17] Ormerod, M.G.; Orr, R.M.; Peacock, J.H. The role of apoptosis in cell killing by cisplatin: a flow cytometric study. Br. J. Cancer. 1994, 69, 93-100
  • [18] Claudia, B.; Ioana, B.; Ovidiu, B.; Alexandru, I. Apoptosis in cancer: Key molecular signaling pathways and therapy targets. Act. Oncol. 2009, 48, 811-821
  • [19] Sreejayan, N.; Rao, M.N.A. Free radical scavenging activity of curcuminoids. Drug. Res. 1996, 46, 169-172
  • [20] Manjula, S.N.; Kenganora, M.; Parihar, V.K.; Kumar, S.; Nayak, P.G.; Kumar, N.; Pai, K.S.R.; Rao, C.M. Antitumor and antioxidant activity of Polyalthia longifolia stem bark ethanol extract. Pharm. Biol. 2010, 48(6), 690-696
  • [21] Vaijanathappa, J.; Badami, S.; Bhojraj, S. In vitro antioxidant activity of Enieostemma axillare. J. Health Sci. 2008, 54(5), 524-528
  • [22] Veerapur, V.P.; Prabhakar, K.R.; Parihar, V.K.; Kandadi, M.R.; Ramakrishana, S.; Mishra, B.; Rao, B.S.S.; Srinivasan, K.K.; Priyadarsini, K.I.; Unnikrishnan, M.K. Ficus racemosa stem bark extract: A potent antioxidant and a probable natural radioprotector. Evidence based complement. Alternat. Med. 2009, 6(3), 317-324
Document Type
short_communication
Publication order reference
Identifiers
YADDA identifier
bwmeta1.element.psjd-7ff1a329-395a-4eaa-8649-70d36874da94
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.