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IJSTR >> Volume 8 - Issue 8, August 2019 Edition

International Journal of Scientific & Technology Research  
International Journal of Scientific & Technology Research

Website: http://www.ijstr.org

ISSN 2277-8616

Tandem Synthesis And Antibacterial Studies Of Novel 3-Substituted Tetrahydrobenzo [4,5] Thieno [1,2,4] Triazolo [4,3-B] Pyridazine And 2- (5- (Substituted) -4h-1,2,4-Triazole-3-Yl) -Tetrahydrobenzo [B] Thiophene-3-Carbonitirile Derivatives

[Full Text]



N. Devika, J. Sembian Ruso, M. Mariyappan, N. Sivakumar



1,2,4-triazolopyridazine, 6,7,8,9-tetrahydrobenzothienopyridazine, Boronic acid, and Antibacterial activity.



A series of novel 3-substituted tetrahydrobenzo [4,5] thieno [1,2,4] triazolo [4,3-b] pyridazine and 2- (5- (substituted) -4H-1,2,4-triazole-3-yl) -4,5,6,7-tetrahydrobenzo [b] thiophene-3-carbonitrile derivative were synthesized. The structures of all derivatives were characterized by LCMS, 1H NMR 13C NMR spectroscopy. Newly synthesized compounds (8a-8f) and (9a-9h) were subjected for their invitro antibacterial screening against Bacillus substilis, Staphylococcus aureus, Klebsiella pneumonia, Escherichia coli R. solanacearum Among the tested compounds, compounds 7d, 7f and 8f exhibited significant antibacterial activity.



[1]. Mangalagiu I,Grosu G, and Petrovanu M, “Antimicrobial activity of new pyridazine derivative”s, Ann Pharm Fr 1997 ; 55: 69 .
[2]. Galtie C, Mavel S, Snoeck R, Andre G, et al , “Synthesis and antiviral activities of 3-aralkyl-thiomethylimidazo [1,2-b] pyridazine derivatives”, Anti. Chem and Chemo2003; 14: 177.
[3]. Islam M, Siddiqui A, Rajes R, “Synthesis and antimicrobial activity of some novel oxadiazole derivatives”,Acta Pol Pharm 2008; 65: 441 .
[4]. Yassin F.A, “Novel pyrazolyl pyridazine derivatives likely to possess anti- inflammatory activity”,Chem. Heterocycl. Comp 2009; 45 : 997 .
[5]. Zhou J, Fan H.T , Song B.A, Jin L.H, Bhadury P.S, Hu D.Y, “Synthesis and antiviral activities of α-aminophosphonate derivatives containing a pyridazine moiety”, Phosphorus, Sulfur, and Silicon and the Relat Elem 2010; 186: 81.
[6]. Bloomer L.C, Wotring L.L, Townsend L.B, “Cytotoxity of a New Uridine Analog, 4-Hydroxy-1- (B-D-ribofuranosyl) -Pyridazin-6-One, and its interaction with uridine kinase”, Cancer Res 1982; 42: 100.
[7]. Katz D.J, Wise D.S, Townsend L.B, “Synthesis of pyridazine analogs of the naturally occurring nucleosides cytidine, uridine, deoxycytidine and deoxyuridine”, J. Med. Chem 1982; 25: 813.
[8]. Corina M, Casiraghi G, Zetta L.C, “ C-Heteroarylation of sugars by indolylbromomagnesium salts. Synthesis of 3- (alditol-1-yl) indoles and their cyclization to indole C-nucleoside analogs”, J. Org. Chem 1991 ; 56: 5466 .
[9]. Abubshai S.A, “ An Efficient Synthesis and Reactions of Novel indolyl- pyridazinone derivatives with expected biological activity”, Molecule 2007 ;12 : 25 .
[10]. Yokoyama M, Tanabe T, Toyoshima A, Togo H, “ Synthesis of C-ribo-nucleosides having typical Aromatic heterocycles as base moiety”, Chem Lett 1994 ; 517: 265 .
[11]. Mantu D, Catalina Luca M.C, Moldoveanu C, Zbancioc G, Mangalagiu I.I, “ Synthesis and antituberculosis activity of some new pyridazine derivatives”, Part II Eur. J. Med.Chem 2010 ; 45: 5164 .
[12]. Malinka W, Redizicka A, Lozach O, “New derivatives of pyrrolo [3,4-d] pyridazinone and their anticancer effect”s, Farmaco 2004 ;59 : 457.
[13]. Ulusoy N, Gursoy A.G, Otuk G, “ Synthesis and antimicrobial activity of some 1,2,4-triazole-3-mercaptoacetic acid derivative”s, Farmaco 2001 ; 56: 947.
[14]. Papakostantinou Garoufalias S, Pouli N, Marakos P, Chytyroglou Ladas A , “Synthesis antimicrobial and antifungal activity of some new 3-substituted derivatives of 4- (2,4-dichlorophenyl) -5-adamantyl-1H-1,2,4-triazole”, Farmaco 2002 ; 57: 973.
[15]. Kucukguzel I.I, Guniz Kucukguzel S.G.S, Rollas S.S, Kiraz M.M, “Some 3-thioxo/alkylthio-1,2,4-triazoles with a substituted thiourea moiety as possible antimycobacterials”, Bioorg Med. Chem. Lett 2001 ; 11: 1703 .
[16]. Patel N.B, Khan I.H, Rajani S.D, “Pharmacological evaluation and characterizations of newly synthesized 1,2,4-triazoles”, Eur. J. Med. Chem 2010 ; 45 : 4293 .
[17]. Shiradkar M, Kumar G.V.S, Dasari V, Tatikonda S, Akula K.C, Shah R, “ A clubbed triazole: A noval approach to anti tubercular drugs”, Eur. J. Med. Chem 2007; 42: 807 .
[18]. Parmar S.S, Gupta A.K, Singh H.H, Gupta T.K, “Benzimidazolyl-1,2,4 (H) -triazoles as central nervous system depressants”, J. Med. Chem. 1972; 15 : 999 .
[19]. Wang L.C, Tu C.H, Wang J.H, Lee G.H, “Synthesis and molecular structure of 6-amino-3-benzylmercapto-1,2,4-triazolo [3,4-f] [1,2,4] triazin-8 (7H) -one”,Molecule2006;11:169 .
[20]. Zitouni G.T, Kaplanciki Z.A, Ozdemir A, Chevallet P, Kandilci H.B, Gumusel B, “Antimicrobial activities of novel 3-substituted [1,2,4] triazolo [4,3-b] pyridazines derivatives”, Arch. Pharm. Chem. Life. Sci 2007; 11: 586 .
[21]. Nagamatsu T, Ahamed S, Hossion A.M.L, Ohno. “Synthesis of new sulfur-linked di- and triheterocyclic compounds containing thienotriazolopyrimidine and triazolothiadiazole moieties”, Hetrocycles 2007 ; 73: 777 .
[22]. Shawali A.S, Hassaneen H.M, Shurrab N.K, “A new strategy for the synthesis of
pyrazolo [4,3-e] [1,2,4] triazolo [4,3-c] pyrimidines and pyrazolo [4,3-e] [1,2,4] triazolo [1,5-c] pyrimidines”, Tetrahedron 2008 ; 64 : 10339 .
[23]. Ashalatha B.V.B, Narayana B, Vijaya Raj K.K, Suchetha Kumari N, “Synthesis of some bioactive 2-bromo-5-methoxy-N'- [4- (aryl) -1,3-thiazol-2-yl] benzohydrazide derivatives”, Eur J Med. Chem 2007 ; 47: 19.
[24]. Biagi G, Giorgi I, Livi O , Manera C , Scartoni V, Lucacchini A, Senatore G, “ 1,2,3-Triazolo [4,5-d] pyridazines , Preparation and adenosine receptor binding of new 4-amino derivatives”, Farmaco 1996 ; 51: 601.
[25]. Atack J.R, Wong D.F, Fryer T.D, Ryan C , et al.“Benzodiazepine binding site occupancy by the novel GABAA receptor subtype-selective drug 7- (1,1-dimethylethyl) -6- (2-ethyl-2H-1,2,4-triazol-3-ylmethoxy) -3- (2-fluorophenyl) -1,2,4-triazolo [4,3-b] pyridazine (TPA023) in rats, primates, and humans”, Pharmacol Ther. 2010 ;32: 17.
[26]. Licata S.C, Platt D.M, Rüedi Bettschen D, Atack J.R, Dawson G.R , Van Linn M.L , Cook J.M, Rowlett J.K, Neuropharmacology 2010 ;58 : 357 .
[27]. Albright J.D, Moran D.P, Wright W.B, Collins J.P, Beer B, Lipa A.S, Greenblatt E.N, “ Synthesis and anxiolytic activity of 6- (substituted-phenyl) -1,2,4-triazolo [4,3-b] pyridazines”, J. Med. Chem 1981; 24: 592.
[28]. Nagamatsu T, Ahamed S, Hossion A.M.L, Ohno, “ Synthesis of new sulfur-linked di- and triheterocyclic compounds containing thienotriazolopyrimidine and triazolothiadiazole moieties”, Hetrocycles 2007 ;73: 777.
[29]. Ullrich M, Tony D, Peter B, “Structure-property relationships in mixed oligo heterocycles based on end-capped oligothiophenes”, Eur. J. Org. Chem 2000 ; 3: 425 .
[30]. Okeke M.I, Iroegbu C.U, Eze E.N, Okoli A.S, Esimone C.O, “ Evaluation of extracts of the root of landolphia owerrience for antibacterial activity”, J. Ethnopharmacology 2001 ; 78 :19.
[31]. Hammer K.A, Carson C.F, Riley T.V, “Antimicrobial activity of essential oils and other plantextracts” ,J. Applied Microbiology 1999 ; 86: 985.
[32]. Rajasekaran C, Meignanam E, Vijayakumar V, Kalaivani T, Ramya S, Premkumar N, Siva R, Jayakumararaj R, “Investigation on Antibacterial activity of leaf extract of Azadirachta indica A. Juss (Meliacea) : A traditional medicine plant of india”, Ethnobotanical Leaflets 2008 ;12: 1213 .