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

Nair, Ramya and Kumari, Sandya MV and Kalthur, Guruprasad and Adiga, Satish Kumar (2014) Synthesis of novel thiadiazolotriazin-4-ones and study of their mosquito-larvicidal and antibacterial properties. European Journal of Medicinal Chemistry, 84. pp. 194-199. ISSN 0223-5234

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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 e5n) 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.

Item Type: Article
Uncontrolled Keywords: Thiadiazolotriazin-4-one; Mosquito-larvicidal studies; Antibacterial studies; 1,3,4-Thiadiazole moiety; Triazin-4-one moiety.
Subjects: Medicine > KMC Manipal > Obstetrics & Gynaecology
Depositing User: KMC Manipal
Date Deposited: 26 Aug 2014 11:46
Last Modified: 26 Aug 2014 11:46
URI: http://eprints.manipal.edu/id/eprint/140471

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