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

Research output: Contribution to journalArticle

4 Citations (Scopus)

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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Culicidae
Pyruvic Acid
Malaria
Ethanol
Nuclear magnetic resonance
Acids
Pathogens
Pharmaceutical Preparations
Derivatives
1,2,4-triazine
Proton Magnetic Resonance Spectroscopy
Carbon-13 Magnetic Resonance Spectroscopy
thiocarbohydrazide
alpha-ketobutyric acid

All Science Journal Classification (ASJC) codes

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

Cite this

Castelino, Prakash Anil ; Naik, Prashantha ; Dasappa, Jagadeesh Prasad ; Sujayraj, R. S. ; Sharath Chandra, K. ; Chaluvaiah, Kumara ; Nair, Ramya ; Sandya Kumari, M. V. ; Kalthur, Guruprasad ; Adiga, Satish Kumar. / Synthesis of novel thiadiazolotriazin-4-ones and study of their mosquito-larvicidal and antibacterial properties. In: European Journal of Medicinal Chemistry. 2014 ; Vol. 84. pp. 194-199.
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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.",
author = "Castelino, {Prakash Anil} and Prashantha Naik and Dasappa, {Jagadeesh Prasad} and Sujayraj, {R. S.} and {Sharath Chandra}, K. and Kumara Chaluvaiah and Ramya Nair and {Sandya Kumari}, {M. V.} and Guruprasad Kalthur and Adiga, {Satish Kumar}",
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Castelino, PA, Naik, P, Dasappa, JP, Sujayraj, RS, Sharath Chandra, K, Chaluvaiah, K, Nair, R, Sandya Kumari, MV, Kalthur, G & Adiga, SK 2014, 'Synthesis of novel thiadiazolotriazin-4-ones and study of their mosquito-larvicidal and antibacterial properties', European Journal of Medicinal Chemistry, vol. 84, pp. 194-199. https://doi.org/10.1016/j.ejmech.2014.06.072

Synthesis of novel thiadiazolotriazin-4-ones and study of their mosquito-larvicidal and antibacterial properties. / Castelino, Prakash Anil; Naik, Prashantha; Dasappa, Jagadeesh Prasad; Sujayraj, R. S.; Sharath Chandra, K.; Chaluvaiah, Kumara; Nair, Ramya; Sandya Kumari, M. V.; Kalthur, Guruprasad; Adiga, Satish Kumar.

In: European Journal of Medicinal Chemistry, Vol. 84, 12.09.2014, p. 194-199.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis of novel thiadiazolotriazin-4-ones and study of their mosquito-larvicidal and antibacterial properties

AU - Castelino, Prakash Anil

AU - Naik, Prashantha

AU - Dasappa, Jagadeesh Prasad

AU - Sujayraj, R. S.

AU - Sharath Chandra, K.

AU - Chaluvaiah, Kumara

AU - Nair, Ramya

AU - Sandya Kumari, M. V.

AU - Kalthur, Guruprasad

AU - Adiga, Satish Kumar

PY - 2014/9/12

Y1 - 2014/9/12

N2 - 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.

AB - 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.

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