title: Synthesis of novel thiadiazolotriazin-4-ones and study of their mosquito-larvicidal and antibacterial properties.
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, (1)H NMR, (13)C 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.
authors.affiliation: Department of Chemistry, Mangalore University, Mangalagangothri 574 199, Karnataka State, India.
authors.forename: Prakash Anil
authors.initials: PA
authors.lastname: Castelino
authors.affiliation: Department of Biosciences, Mangalore University, Mangalagangothri 574 199, Karnataka State, India.
authors.forename: Prashantha
authors.initials: P
authors.lastname: Naik
authors.affiliation: Department of Chemistry, Mangalore University, Mangalagangothri 574 199, Karnataka State, India. Electronic address: jprasad2003@gmail.com.
authors.forename: Jagadeesh Prasad
authors.initials: JP
authors.lastname: Dasappa
authors.affiliation: Department of Biosciences, Mangalore University, Mangalagangothri 574 199, Karnataka State, India.
authors.forename: R S
authors.initials: RS
authors.lastname: Sujayraj
authors.affiliation: Department of Biosciences, Mangalore University, Mangalagangothri 574 199, Karnataka State, India.
authors.forename: K
authors.initials: K
authors.lastname: Sharath Chandra
authors.affiliation: Department of Chemistry, Mangalore University, Mangalagangothri 574 199, Karnataka State, India.
authors.forename: Kumara
authors.initials: K
authors.lastname: Chaluvaiah
authors.affiliation: Division of Clinical Embryology, Kasturba Medical College, Manipal University, Manipal 576 104, Karnataka State, India.
authors.forename: Ramya
authors.initials: R
authors.lastname: Nair
authors.affiliation: Division of Clinical Embryology, Kasturba Medical College, Manipal University, Manipal 576 104, Karnataka State, India.
authors.forename: M V
authors.initials: MV
authors.lastname: Sandya Kumari
authors.affiliation: Division of Clinical Embryology, Kasturba Medical College, Manipal University, Manipal 576 104, Karnataka State, India.
authors.forename: Guruprasad
authors.initials: G
authors.lastname: Kalthur
authors.affiliation: Division of Clinical Embryology, Kasturba Medical College, Manipal University, Manipal 576 104, Karnataka State, India.
authors.forename: Satish Kumar
authors.initials: SK
authors.lastname: Adiga
mesh_terms: D000818:Animals; D000852:Anopheles / Q000187:drug effects* / Q000254:growth & development; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D006090:Gram-Negative Bacteria / Q000187:drug effects*; D006094:Gram-Positive Bacteria / Q000187:drug effects*; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D007814:Larva / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013830:Thiadiazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D014227:Triazines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: C000596756:3-tert-butyl-7-(2-(4-chlorophenoxy)propan-2yl)-4H-(1,3,4)thiadiazolo(2,3-c)(1,2,4)triazin-4-one; C000596757:7-((4-acetylphenoxy)methyl)-3-tert-butyl-4H-(1,3,4)thiadiazolo(2,3-c)(1,2,4)triazin-4-one; D000900:Anti-Bacterial Agents; D007306:Insecticides; D013830:Thiadiazoles; D014227:Triazines
keywords: 1,3,4-Thiadiazole moiety; Antibacterial studies; Mosquito-larvicidal studies; Thiadiazolotriazin-4-one; Triazin-4-one moiety