Abstract
A new series of 2-amino-5-sulfanyl-1,3,4-thiadiazole derivatives has been synthesized. The newly synthesized compounds were characterized by analytical and spectral methods. Compounds were screened for central nervous system activity. Compounds 1, 5, 7, 10, 14 exhibited significant antidepressant, anxiolytic and anticonvulsant activity in comparison to the reference drugs.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Ahmadiani A, Mandgary A, Sayyah M (2003) Anticonvulsant effect of flutamide on seizures induced by pentylene tetrazole: involvement of benzodiazepine receptors. Epilepsia 44:629–635
Ambawade A, Kasture VS, Kasture SB (2002) Anticonvulsant activity of roots and rhizomes of glycyrhiza glabra. Ind J Pharmacol 34:251–255
Chapleo CB, Myers M, Myers PL, Saville JF, Smith ACB, Stillings MR, Tulloch IF, Walter DS, Welbourn AS (1986) Substituted 1,3,4-thiadiazoles with anticonvulsant activity: 1-Hydrazines. J Med Chem 29:2273–2280
Clerici F, Pocar D (2001) Synthesis of 2-amino-5-sulfanyl-1,3,4-thiadiazole derivatives and evaluation of their antidepressant and anxiolytic activity. J Med Chem 44:931–936
Crawley J, Goodwin KK (1980) Preliminary report of a simple animal behavior model for the anxiolytic effects of benzodiazepines. Pharmacol Biochem Behav 13:167–170
Jones DH, Slack S, Squires S, Wooldridge KH (1965) Antiviral chemotherapy: 1. The activity of pyridine and quinoline derivatives against neurovaccinia in mice. J Med Chem 8:676–680
Matysiak J (2006) Evaluation of antiproliferative effect in vitro of some 2-amino-5-(2,4-dihydroxyphenyl)-1,3,4-thiadiazole derivatives. Chem Pharm Bull 54:988–991
Milan MJ (2003) The neurobiology and control of anxious states. Prog Neurobiol 70:83–244
Misra AK, Dandiya PC, Kulkarni SK (1973) Anticonvulsant activity of some trimethoxybenzylidene-2-thiohydantion derivatives. Ind J Pharmacol 5:449–450
Moser PC (1989) An evaluation of the elevated plus-maze test using the novel anxiolytic Buspiron. Psychopharm 99:48–53
Mullican MD, Wilson MW, Connor DT, Kostlan CR, Schrier DJ (1993) Design of 5-(3,5-di-tert-butyl-4-hydroxyphenyl)1,3,4-thiadiazole,1,3,4-oxadiazoles and 1,2,4-triazole as orally active nonulcerogenic antiinflammatory agent. J Med Chem 36:1090–1099
Oruç EE, Rollas S, Kandemirli F, Shvets N, Dimoglo AS (2004) 1,3,4-Thiadiazole derivatives: synthesis, structure elucidation, and structure-anti-tuberculosis activity relationship investigation. Bioorg Med Chem Lett 12:5651–5659
Porsolt RD, Le Pichon M, Jalfre M (1977) Depression: a new animal model sensitive to antidepressant treatments. Nature 266:730–732
Rabbani M, Sajjadi SE, Vaseghi G, Jafarian A (2004) Anxiolytic effects of Echium amoenum on the elevated plus maze model of anxiety in mice. Fitoterapia 75:464–475
Schenone S, Brullo C, Bondavalli F, Ranise A, Filippelli W, Rinaldi B, Capuano A, Falcone G (2006) New 1,3,4-thiadiazole derivatives endowed with analgesic and anti- inflammatory activities. Bioorg Med Chem 14:1698–1705
Servi S, Genc M, Gür S, Koca M (2005) The synthesis and antimicrobial activity of some new methyl N-arylthiocarbamates, dimethyl N-aryldithiocarbonimidates and 2-arylamino-2-imidazolines. Eur J Med Chem 40:687–693
Shah P, Westwell AD (2007) The role of flurine in medicinal chemistry. J Enzyme Inhib Med Chem 22:527–540
Shalam MD, Shantakumar SM, Laxmi N (2007) Possible anxiolytic activity of trans-o1, a polyherbal formulation in mice. Pharmacologyonline 1:138–145
Sharma JD, Dandiya PC (1962) Studies on C. N. S. depressants (I): general pharmacological actions of trimeglamide. Arch Int Pharmacodyn 137:218–230
Steru L, Chermat R, Thierry B, Simon P (1985) Tail suspension test: a new method for screening antidepressants in mice. Psychopharm 85:367–370
Stillings MR, Welbournt AP, Walter DS (1986) Substituted 1,3,4-thiadiazoles with anticonvulsant activity, 2-aminoalkyl derivatives. J Med Chem 29:2280–2284
Woodbury LA, Davenport VO (1952) Design and use of a new electroshock seizure apparatus and analysis of factors altering seizure threshold and pattern. Arch Int Pharmocodyn 92:97–107
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Sharma, R., Misra, G.P., Sainy, J. et al. Synthesis and biological evaluation of 2-amino-5-sulfanyl-1,3,4-thiadiazole derivatives as antidepressant, anxiolytics and anticonvulsant agents. Med Chem Res 20, 245–253 (2011). https://doi.org/10.1007/s00044-010-9308-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00044-010-9308-3