Medicinal Chemistry Research

, Volume 26, Issue 7, pp 1359–1366 | Cite as

Synthesis of N′-arylidene-2-(5-aryl-1H-1, 2, 4-triazol-3-ylthio) acetohydrazides as antidepressants

  • Radhika Chelamalla
  • Venkatesham Akena
  • Sarangapani Manda
Original Research


A series of N′-arylidene-2-(5-aryl-1H-1, 2, 4-triazol-3-ylthio) acetohydrazide were synthesized. Condensation of aromatic aldehydes with 2-(5-aryl-1H-1, 2, 4-triazol-3-ylthio) acetohydrazide gave corresponding N′ -arylidene-2-(5-aryl-1H-1, 2, 4-triazol-3-ylthio) acetohydrazide. Spectral and elemental analysis was used for structural elucidation of novel 1, 2, 4-triazole schiff bases. The newly synthesized compounds were screened for their antidepressant activity by using tail suspension test in mice. Compound 4l showed significant activity among the series.

Graphical Abstract

A series of new N′-arylidene-2-(5-aryl-1H-1, 2, 4-triazol-3-ylthio)acetohydrazide have been synthesized and characterized. The results revealed that compound 4l with bromo substitution exhibited promising antidepressant activity among the series. Open image in new window


Antidepressant activity 1, 2, 4-triazole Acetohydrazide Schiff base Structure-activity relationships 



The authors are thankful to IICT Hyderabad for providing 1H NMR, IR, Mass spectra, and elemental analysis of the compounds. Thanks are also to the management of Malla Reddy group of Institutions for providing research facilities.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no competing interests.


  1. Aouad MR, Messali M, Rezki N, Ali AA, Lesimple A (2015) Synthesis and characterization of some novel 1,2,4-triazoles, 1,3,4-thiadiazoles and Schiff bases incorporating imidazole moiety as potential antimicrobial agents. Acta Pharm 65:117–132CrossRefPubMedGoogle Scholar
  2. Cryan JF, Mombereau C, Vassout A (2005) The tail suspension test as a model for assessing antidepressant activity: review of pharmacological and genetic studies in mice. Neurosci Biobehav Rev 29:571–625CrossRefPubMedGoogle Scholar
  3. Flefel EM, Tantawy WA, El-Sayed WA, Sayed HH, Fathy NM (2013) Synthesis and anticancer activity of new substituted pyrazoles and their derived 1,2,4-Triazoles and sugar derivatives. J Heterocycl Chem 50:344–350CrossRefGoogle Scholar
  4. Jiang B, Huang X, Yao H, Jiang J, Wu X, Jiang S, Wang Q, Lu T, Xu J (2014) Discovery of potential anti-inflammatory drugs: diaryl-1,2,4-triazoles bearing N-hydroxyurea moiety as dual inhibitors of cyclooxygenase-2 and 5-lipoxygenase. Org Biomol Chem 12:2114–2117CrossRefPubMedGoogle Scholar
  5. Jubie S, Sikdar P, Antony S, Kalirajan R, Gowramma B, Gomathy S, Elango K (2011) Synthesis and biological evaluation of some schiff bases of [4-(amino)-5-phenyl-4H-1, 2,4-triazole-3-thiol]. Pak J Pharm Sci 24:109–112PubMedGoogle Scholar
  6. Kamboj VK, Verma PK, Dhanda A, Ranjan S (2015) 1, 2, 4-triazole derivatives as potential scaffold for anticonvulsant activity. Cent Nerv Syst Agents Med Chem 15:17–22CrossRefPubMedGoogle Scholar
  7. Kamel MM, Abdo NYM (2014) Synthesis of novel 1,2,4-triazoles, triazolothiadiazines and triazolothiadiazoles as potential anticancer agents. Eur J Med Chem 86:75–80CrossRefPubMedGoogle Scholar
  8. Li C, Liu JC, Li YR, Gou C, Zhang ML, Liu HY, Li XZ, Zheng CJ, Piao HR (2015) Synthesis and antimicrobial evaluation of 5-aryl-1,2,4-triazole-3-thione derivatives containing a rhodanine moiety. Bioorg Med Chem Lett 25:3052–3056CrossRefPubMedGoogle Scholar
  9. Li X, Li XQ, Liu HM, Zhou XZ, Shao ZH (2012) Synthesis and evaluation of antitumor activities of novel chiral 1, 2, 4-triazole Schiff bases bearing γ-butenolide moiety. Org Med Chem Lett 2:26–30CrossRefPubMedPubMedCentralGoogle Scholar
  10. Maddila S, Jonnalagadda SB (2012) New class of triazole derivatives and their antimicrobial activity. Lett Drug Des Discov 9:687–693CrossRefGoogle Scholar
  11. Mange YJ, Isloor AM, Malladi S, Isloor S, Fun HK (2013) Synthesis and antimicrobial activities of some novel 1,2,4-triazole derivatives. Arabian J Chem 6:177–181CrossRefGoogle Scholar
  12. McNamara JO (2011) Pharmacotherapy of the epilepsies. In: Brunton L, Chabner B, Knollmann B (eds) Goodman & Gilman’s the Phamacological Basis of Therapeutics, 12th ed. McGraw-Hill, New York, NY, pp 583–608Google Scholar
  13. Panda SS, Jain SC (2014) Synthesis and QSAR studies of some novel didistributed 1, 2, 4-triazoles as aantimicrobial agents. Med Chem Res 23:848–861CrossRefGoogle Scholar
  14. Plech T, Luszczki JJ, Wujec M, Flieger J, Pizon M (2013) Synthesis, characterization and preliminary anticonvulsant evaluation of some 4-alkyl-1,2,4-triazoles. Eur J Med Chem 60:208–215CrossRefPubMedGoogle Scholar
  15. Sarigol D, Uzgoren-Baran A, Tel BC, Somuncuoglu EI, Kazkayasi I, Ozadali-Sari K, Unsal-Tan O, Okay G, Ertan M, Tozkoparan B (2015) Novel thiazolo[3,2-b]-1,2,4-triazoles derived from naproxen with analgesic/anti-inflammatory properties: Synthesis, biological evaluation and molecular modeling studies. Bioorg Med Chem 23:2518–2528CrossRefPubMedGoogle Scholar
  16. Sim KM, Loo ST, Teo KC (2014) Synthesis, characterization, antibacterial and free radical scavenging activities of some new 1,2,4-triazole Schiff bases and Mannich bases. Lett Org Chem 11:564–572CrossRefGoogle Scholar
  17. Singh R, Pujar GV, Purohit MN, Chandrashekar M (2013) Synthesis, in vitro cytotoxicity, and antibacterial studies of new asymmetric bis-1,2,4-triazoles. Med Chem Res 22:2163–2173CrossRefGoogle Scholar
  18. Song MX, Zhang CB, Deng XQ, Sun ZG, Quan ZS (2011) Synthesis and anticonvulsant activity evaluation of 6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines. Lett Drug Des Discov 8:769–773CrossRefGoogle Scholar
  19. Tozkoparan B, Kupeli E, Yesilada E, Ertan M (2007) Preparation of 5-aryl-3-alkylthio-l, 2, 4-triazoles and corresponding sulfones with antiinflammatory–analgesic activity. Bioorg Med Chem 15:1808–1814CrossRefPubMedGoogle Scholar
  20. Zamani K, Faghihi K, Sangi MR, Zolgharnein J (2003) Synthesis of some new substituted 1, 2, 4-triazole and 1, 3, 4-thiadiazole and their derivatives. Turk J Chem 27:119–125Google Scholar

Copyright information

© Springer Science+Business Media New York 2017

Authors and Affiliations

  • Radhika Chelamalla
    • 1
  • Venkatesham Akena
    • 2
  • Sarangapani Manda
    • 2
  1. 1.Center for Pharmaceutical SciencesJawaharlal Nehru Technological University, KukatpallyHyderabadIndia
  2. 2.University College of Pharmaceutical Sciences, Kakatiya UniversityWarangalIndia

Personalised recommendations