Studies on fused heterocyclic 3,6-disubstituted-1,2, 4-triazolo-1,3,4- thiadiazoles: Synthesis and biological evaluation

Medicinal Chemistry Research

Volumn 20, Issue 1, 2011, Pages 47-54

  Husain, Asif ^a   Naseer, Md Arif ^a  

^a HAMDARD UNIVERSITY   (India)

Author keywords

Anti inflammatory; Fused heterocycles; Triazolothiadiazoles; Ulcerogenic

Indexed keywords

3 (2 HYDROXYPHENYL) 6 (1 NAPHTHYL)[1,2,4]TRIAZOLO[3,4 B] [1,3,4]THIADIAZOLE; 3 (2 HYDROXYPHENYL) 6 (2 BROMOPHENYL)[1,2,4]TRIAZOLO[3,4 B] [1,3,4]THIADIAZOLE; 3 (2 HYDROXYPHENYL) 6 (3 BROMOPHENYL)[1,2,4]TRIAZOLO[3,4 B] [1,3,4]THIADIAZOLE; 3 (2 HYDROXYPHENYL) 6 (4 BROMOPHENYL)[1,2,4]TRIAZOLO[3,4 B] [1,3,4]THIADIAZOLE; 3 (2 HYDROXYPHENYL) 6 PHENYLCARBOXAMIDOMETHYL[1,2,4]TRIAZOLO[3,4 -B] [1,3,4]THIADIAZOLE; 3 BENZYL 6 (1 NAPHTHYLMETHYL)[1,2,4]TRIAZOLO[3,4 B] [1,3,4]THIADIAZOLE; 3 BENZYL 6 (1H 2 INDOLYLMETHYL)[1,2,4]TRIAZOLO[3,4 B] [1,3,4]THIADIAZOLE; 3 BENZYL 6 (2 BENZOYLPHENYL)[1,2,4]TRIAZOLO[3,4 B] [1,3,4]THIADIAZOLE; 3 BENZYL 6 (2 BROMOPHENYL)[1,2,4]TRIAZOLO[3,4 B] [1,3,4]THIADIAZOLE; 3 BENZYL 6 (3 BROMOPHENYL)[1,2,4]TRIAZOLO[3,4 B] [1,3,4]THIADIAZOLE; 3 BENZYL 6 (4 BROMOPHENYL)[1,2,4]TRIAZOLO[3,4 B] [1,3,4]THIADIAZOLE; 3 BENZYL 6 PHENYLCARBOXAMIDOMETHYL[1,2,4]TRIAZOLO 3,4 B [1,3,4]THIADIAZOLE; 3 PHENOXYMETHYL 6 (1 NAPHTHYLMETHYL)[1,2,4]TRIAZOLO[3,4 B] [1,3,4]THIADIAZOLE; 3 PHENOXYMETHYL 6 (1H 2 INDOLYLMETHYL)[1,2,4]TRIAZOLO[3,4 B] [1,3,4]THIADIAZOLE; 3 PHENOXYMETHYL 6 (2 BENZOYLPHENYL)[1,2,4]TRIAZOLO[3,4 B] [1,3,4]THIADIAZOLE; 3 PHENOXYMETHYL 6 (2 BROMOPHENYL)[1,2,4]TRIAZOLO[3,4 B] [1,3,4]THIADIAZOLE; 3 PHENOXYMETHYL 6 (3 BROMOPHENYL)[1,2,4]TRIAZOLO[3,4B] [1,3,4]THIADIAZOLE; 3 PHENOXYMETHYL 6 (3 OXO 3 PHENYLPROPYL)[1,2,4]TRIAZOLO[3,4 B] [1,3,4]THIADIAZOLE; 3 PHENOXYMETHYL 6 (4 BROMOPHENYL)[1,2,4]TRIAZOLO[3,4 B] [1,3,4]THIADIAZOLE; 3 PHENOXYMETHYL 6 PHENYLCARBOXAMIDOMETHYL[1,2,4]TRIAZOLO[3,4 B] [1,3,4]THIADIAZOLE; ACETYLSALICYLIC ACID; ANALGESIC AGENT; ANTIINFLAMMATORY AGENT; INDOMETACIN; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SAFETY; DRUG SCREENING; DRUG SYNTHESIS; FEMALE; LIPID PEROXIDATION; MALE; MOUSE; NONHUMAN; RAT; ULCEROGENESIS; WRITHING TEST;

EID: 79952706343     PISSN: 10542523     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00044-009-9281-x     Document Type: Article

References (20)

1. Allison MC, Howatson AG, Torrance CJ, Lee FD, Russell RIG (1992) Gastrointestinal damage associated with the use of Nonsteroidal Antiinflammatory drugs. N Engl J Med 327:749-754
2. Amir M, Kumar H, Javed SA (2007) Synthesis and pharmacological evaluation of condensed heterocyclic 6-substituted-1,2,4-triazolo[ 3,4-b]-1,3,4- thiadiazole derivatives of naproxen. Bioorg Med Chem Lett 17:4504-4508
3. Cioli V, Putzolu S, Rossi V, Sorza Barcellona P, Corradino C (1979) The role of direct tissue contact in the production of gastrointestinal ulcers by anti-inflammatory drugs in rats. Toxicol Appl Pharrmacol 50:283-289 (Pubitemid 10233388)
4. Collier HO, Dinneen LC, Johnson CA, Schneider C (1968) The abdominal constriction response and its suppression by analgesic drugs in the mouse. Br J Pharmacol 32:295-310
5. Hafez HN, Hegab MI, Ahmed-Farag IS, Gazzar AB (2008) A facile regioselective synthesis of novel spiro-thioxanthene and spiro-xanthene- 9′,2-[1,3,4]thiadiazole derivatives as potential analgesic and anti-inflammatory agents. Bioorg Med Chem Lett 18:4538-4543
6. Karegoudar P, Prasad DJ, Ashok M, Mahalinga M, Poojary B, Holla BS (2008) Synthesis, antimicrobial and antiinflammatory activities of some 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles and 1,2,4- triazolo[3,4-b][1,3,4] thiadiazines bearing trichlorophenyl moiety. Eur J Med Chem 43:808-815
7. Karthikeyan MS, Holla BS, Kulkuraya B, Kumari NS (2007) Biological studies of some 2,4-dichloro-5-fluorophenyl containing triazolothiadiazoles. Monatshette fur chemie 138:1309-1316
8. Kucukguzel SG, Kucukguzel I, Tatar E, Rollas S, Sahin F, Gulluce M, DeClercq E, Kabasakal L (2007) Synthesis of some novel heterocyclic compounds derived from diflunisal hydrazide as potential anti-infective and anti-inflammatory agents. Eur J Med Chem 42:893-901 (Pubitemid 46907345)
9. Mathew V, Keshavayya J, Vaidya VP (2006) Heterocyclic system containing bridgehead nitrogen atom: synthesis and pharmacological activities of some substituted-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles. Eur J Med Chem 41:1048-1058
10. Mathew V, Giles D, Keshavayya J, Vaidya VP (2009) Studies on synthesis and pharmacological activities of 1,2,4-triazolo[3,4-b]- 1,3,4-thiadiazoles and their dihydro analogues. Arch Pharm 342:210-222
11. Metwally KA, Yaseen SH, Lashine SM, El-Fayomi HM, El-Sadek ME (2007) Non-carboxylic analogues of arylpropionic acids: synthesis, antiinflammatory activity and ulcerogenic potential. Eur J Med Chem 42:152-160
12. Moore RA, Derry S, Phillips CJ, McQuay HJ (2006) Nonsteroidal anti-inflammatory drugs (NSAIDs), cyclooxygenase-2 selective inhibitors (coxibs) and gastrointestinal harm: review of clinical trials and clinical practice. BMC Musculoskelet Disord 7:79-91
13. Okhawa H, Ohishi N, Yagi K (1979) Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction. Anal Biochem 95:351-358 (Pubitemid 9194347)
14. Prasad DJ, Ashok M, Karegoudar P, Poojary B, Holla BS, Kumari NS (2009) Synthesis and antimicrobial activities of some new triazolothiadiazoles bearing 4-methylthiobenzyl moiety. Eur J Med Chem 44:551-557
15. Sharma R, Sainy J, Chaturvedi SC (2008) 2-Amino-5-sulfanyl-1,3,4- thiadiazoles: a new series of cyclooxygenase-2 inhibitors. Acta Pharm 58:317-326
16. Silvia S, Chiara B, Olga B, Francesco B, Angelo R, Walter F, Barbara R, Annalisa C, Giuseppe F (2006) New 1,3,4-thiadiazole derivatives endowed with analgesic and anti-inflammatory activities. Bioorg Med Chem 14:1698-1705
17. Udupi RH, Rajeeva B, Srinivasulu N, Pasha TY, Setty SR, Bhat AR (2004) Synthesis and biological evaluation of some 4-amino- 3[4′-isobutylphenyl]- ethyl-5-mercapto-1,2,4-triazoles. Indian J Heterocycl Chem 13:233-236 (Pubitemid 39360569)
18. Verrico MM, Weber RJ, McKaveney TP, Ansani NT, Towers AL (2003) Adverse drug events involving COX-2 inhibitors. Ann Pharmacother 37:1203-1213 (Pubitemid 37040209)
19. Winter CA, Risley ET, Nuss GW (1962) Carrageenan-induced edema in hind paw of the rat as an assay for antiinflammatory drugs. Proc Soc Exp Biol Med 3:544-547
20. Wollheim FA (2003) New studies of COX-inhibitors, yet issues remain. Lakartidningen 100:2927-2931