Synthesis and biological evaluation of 3,6-dialkylsubstituted-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazoles

  • Vijayendar Venepally
  • K Sirisha
  • C Ganesh Kumar
  • E Vamshi Krishna
  • Sunil Misra
  • Ram Chandra Reddy Jala
Regular Article
  • 106 Downloads

Abstract

A series of 3,6-dialkyl-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazole (10) analogues were prepared through multistep synthesis and evaluated them for their antimicrobial and cytotoxic activities. Synthesis of target compounds was carried out using undecenoic acid as starting material, which is the renewable product of castor oil. The key step in the synthesis was formation of triazolo [3,4-b][1,3,4]thiadiazole using various free fatty acids in presence of \(\hbox {POCl}_{3}\). It was observed that the undecenyl based triazolothiadiazole with butyl (6a), hexyl (6b) and lauryl (6f) derivatives exhibited promising antimicrobial activity against the tested strains. Particularly, Compound 6a exhibited the most promising activity with MIC value 3.9 \(\upmu \hbox {g}/\hbox {mL}\) against most of the tested strains. It also showed potent minimum bactericidal concentration activity with MIC value 7.8 \(\upmu \hbox {g}/\hbox {mL}\) against the tested strains. Cytotoxicity data revealed that most of the tested compounds revealed cytotoxic activity, Compounds 6b, 6d, 6f, 6g, 6h and 6i against SKOV3, 6d, 6e, 6f, 6g, 6h, 6i and 6j against MCF-7 and 6c, 6d, 6e,6g, 6h, 6i and6j against B16–F10 cell lines exhibited significant activities with \(\hbox {IC}_{50}\) values ranged between 13.67 and 18.62 \(\upmu \hbox {M}\). Interestingly, all the compounds were non toxic against Chinese hamster ovary cell (CHO-K1) normal cell.

Graphical Abstract

A series of 3, 6-dialkyl triazolothiadiazole analogues were prepared using undecenoic acid, which is the renewable product of castor oil and evaluated them for their antimicrobial and cytotoxic activities. Few compounds showed good antimicrobial and cytotoxic activities.

Keywords

Di alkyltriazolothiadiazole cytotoxicity antimicrobial butyl hexyl lauryl 

Notes

Acknowledgements

Venepally Vijayendar acknowledges the University Grants Commission (UGC), New Delhi, India, for the financial support extended in the form of Senior Research Fellowship (SRF).

Supplementary material

12039_2018_1423_MOESM1_ESM.pdf (921 kb)
Supplementary material 1 (pdf 920 KB)

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Copyright information

© Indian Academy of Sciences 2018

Authors and Affiliations

  1. 1.Centre for Lipid ResearchCSIR-Indian Institute of Chemical Technology, TarnakaHyderabadIndia
  2. 2.Medicinal Chemistry and Pharmacology DivisionCSIR-Indian Institute of Chemical Technology, TarnakaHyderabadIndia
  3. 3.Pharmacology and Toxicology DivisionCSIR-Indian Institute of Chemical Technology, TarnakaHyderabadIndia
  4. 4.Academy of Scientific and Innovative ResearchNew DelhiIndia

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