Synthesis of novel thiadiazolotriazin-4-ones and study of their mosquito-larvicidal and antibacterial properties

Prakash Anil Castelino, Prashantha Naik, Jagadeesh Prasad Dasappa, R. S. Sujayraj, K. Sharath Chandra, Kumara Chaluvaiah, Ramya Nair, M. V. Sandya Kumari, Guruprasad Kalthur, Satish Kumar Adiga

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Abstract

A series of novel 3-tert-butyl-7-(aryloxymethyl)-4H-[1,3,4]thiadiazolo[2,3- c][1,2,4]triazin-4-ones (5a-5n) were synthesized by refluxing 3,3-dimethyl-2-oxobutanoic acid (trimethyl pyruvic acid) (1) and thiocarbohydrazide (2) in ethanol as solvent for 12 h, to yield 3-mercapto-4-amino-6-tert-butyl-1,2,4-triazine-5(4H)-one (3) (Scheme 1), then the compound (3) was condensed with different substituted aryloxyacetic acids (4) in POCl3 at 90 °C for 8 h (Scheme 2). The structures of the newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR, elemental analyses and mass spectroscopic studies. Few of the synthesized compounds exhibited moderate mosquito-larvicidal and antibacterial activities. Among the novel derivatives, the compound (5f) showed relatively high larvicidal activity against a malaria vector. Compounds (5i) and (5m) exhibited a broad spectrum antibacterial activity against Gram positive and Gram negative species and hence they may be considered as drug candidates for bacterial pathogens.

Original languageEnglish
Pages (from-to)194-199
Number of pages6
JournalEuropean Journal of Medicinal Chemistry
Volume84
DOIs
Publication statusPublished - 12-09-2014

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All Science Journal Classification (ASJC) codes

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

Cite this

Castelino, P. A., Naik, P., Dasappa, J. P., Sujayraj, R. S., Sharath Chandra, K., Chaluvaiah, K., Nair, R., Sandya Kumari, M. V., Kalthur, G., & Adiga, S. K. (2014). Synthesis of novel thiadiazolotriazin-4-ones and study of their mosquito-larvicidal and antibacterial properties. European Journal of Medicinal Chemistry, 84, 194-199. https://doi.org/10.1016/j.ejmech.2014.06.072