Medicinal Chemistry Research

, Volume 24, Issue 4, pp 1558–1567 | Cite as

Synthesis and antitumor activity of 4-cyclohexyl/aryl-5-(pyridin-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thiones

  • Mashooq Ahmad BhatEmail author
  • Mohamed A. Al-Omar
  • Ahmed M. Naglah
  • Mohamed M. Abdulla
  • Hoong-Kun Fun
Original Research


The reaction of 2-isonicotinoyl-N-cyclohexyl/arylhydrazinecarbothioamide (2ar) with sodium hydroxide, in each case, a single product was obtained. The structures of the compounds were confirmed on the basis of their elemental analysis and spectral data. The single crystal X-ray analysis confirmed the structure of these products as N-4-cyclohexyl/aryl-5-(pyridine-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thiones (3ar). The in vitro antitumor activity of compounds was screened against three cell lines; BEL-7402, HUH-7 and HepG2 human hepatoma using MTT assay. Sorafenib (50 µM) was used as a positive control. The results of the MTT-dye reduction assay indicated that most of the compounds exert potent cytotoxic/antiproliferative effect in a time and dose-dependent manner via induced apoptosis of HepG2 cells. Results also showed that the tested compounds could significantly enhance the activity of caspase-3 which plays a very important role as the central effecter during apoptosis. The effect of different substitutions on the aromatic portion on the activity was found to be in the following order CH3 > OCH3 > I > SO2NH2 > OC2H5 > C2H5 > NO2 > Cl > CH3CONH.


Isoniazid 1,2,4-Triazole-3-thione Cytotoxic activity MTT assay 



The authors would like to extend their sincere appreciation to the Deanship of Scientific Research at King Saud University for funding this research group No. (RG 1435-006).

Supplementary material

44_2014_1216_MOESM1_ESM.docx (473 kb)
Supplementary material 1 (DOCX 472 kb)


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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • Mashooq Ahmad Bhat
    • 1
    Email author
  • Mohamed A. Al-Omar
    • 1
  • Ahmed M. Naglah
    • 2
    • 3
  • Mohamed M. Abdulla
    • 4
  • Hoong-Kun Fun
    • 1
  1. 1.Department of Pharmaceutical Chemistry, College of PharmacyKing Saud UniversityRiyadhKingdom of Saudi Arabia
  2. 2.Pharmaceutical Chemistry Department, Drug Exploration & Development Chair, College of PharmacyKing Saud UniversityRiyadhKingdom of Saudi Arabia
  3. 3.Peptide Chemistry Department, Chemical Industries Research DivisionNational Research CentreCairoEgypt
  4. 4.Research Unit6th October CityEgypt

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