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Research Article Open access CC BY 3.0

Uses of 1-Cyanoacetyl-4-Phenyl-3-Thiosemicarbazide in the Synthesis of Antimicrobial and Antifungal Heterocyclic Compounds

Rafat M. Mohareb, Abeer A. Mohamed

International Research Journal of Pure and Applied Chemistry · pp. 144–155 · Published 4 Jul 2012

10.9734/IRJPAC/2012/1334

Abstract

The thiosemicarbazide synthesized from the reaction of cyanoacetylhydrazine phenylisothiocyanate reacted with acetoacetanilide gave the 2-pyridinone derivative 4. The reaction of the latter product with 1,3-dicarbonyl and α-halocarbonyl compounds gave the benzo[c]pyridine derivatives 6a,b and the thiazole derivatives 9a,b, respectively. The reaction with phenylisothiocyanate and elemental sulfur gave the thiazole derivative 14. The latter compound reacted with α-halocarbonyl compounds to give the thiazole products 16a-c. The antimicrobial and antifungal evaluations of the newly synthesized products showed that some compounds have high activity.  

Thiosemicarbazide pyridine thiazole antimicrobial

References (26)

  1. 1 Synthesis and antimicrobial activity of some new thiazole, thiophene and pyrazole derivatives containing benzothiazole moiety [DOI]
  2. 2 Synthesis and biological evaluation of new 3-substituted indole derivatives as potential anti-inflammatory and analgesic agents [DOI]
  3. 3 Sulfonamide-1,2,4-triazole derivatives as antifungal and antibacterial agents: Synthesis, biological evaluation, lipophilicity, and conformational studies [DOI]
  4. 4 Synthesis of some new 4(3H)-quinazolinone-2-carboxaldehyde thiosemicarbazones and their metal complexes and a study on their anticonvulsant, analgesic, cytotoxic and antimicrobial activities – Part-1 [DOI]
  5. 5 Synthesis and antimicrobial activity of thiosemicarbazides, s-triazoles and their Mannich bases bearing 3-chlorophenyl moiety [DOI]
  6. 6 Efficient synthesis of 2,4-disubstituted thiazoles using ionic liquid under ambient conditions: a practical approach towards the synthesis of Fanetizole [DOI]
  7. 7 New conditions for the synthesis of thiophenes via the Knoevenagel/Gewald reaction sequence. Application to the synthesis of a multitargeted kinase inhibitor [DOI]
  8. 8 Design and synthesis of 5-alkoxy-[1,2,4]triazolo[4,3-a]quinoline derivatives with anticonvulsant activity [DOI]
  9. 9 Synthesis and evaluation of anti-Toxoplasma gondii and antimicrobial activities of thiosemicarbazides, 4-thiazolidinones and 1,3,4-thiadiazoles [DOI]
  10. 10 Synthesis and anti-microbial activity of some 1- substituted amino-4,6-dimethyl-2-oxo-pyridine-3-carbonitrile derivatives [DOI]
  11. 11 Carbonic anhydrase inhibitors: aromatic and heterocyclic sulfonamides incorporating adamantyl moieties with strong anticonvulsant activity [DOI]
  12. 12 Synthesis and anticonvulsant evaluation of some new 2,3,8-trisubstituted-4(3H)-quinazoline derivatives [DOI]
  13. 13 A solvent-free synthesis of coumarins via Pechmann condensation using heterogeneous catalyst [DOI]
  14. 14 Synthesis of some new hydrazide-hydrazones, thiosemicarbazides and thiazolidinones as possible antimicrobials [DOI]
  15. 15 Synthesis of some novel N4-(naphtha[1,2-d]thiazol-2-yl)semicarbazides as potential anticonvulsants [DOI]
  16. 16 Synthesis and structure–activity relationship studies of 4-arylthiosemicarbazides as topoisomerase IV inhibitors with Gram-positive antibacterial activity. Search for molecular basis of antibacterial activity of thiosemicarbazides [DOI]
  17. 17 Synthesis and anticonvulsant and neurotoxicity evaluation of N4-phthalimido phenyl (thio) semicarbazides [DOI]
  18. 18 Anticonvulsant and neurotoxicity evaluation of some 6-substituted benzothiazolyl-2-thiosemicarbazones [DOI]
  19. 19 Hydantoins, triazolones, and imidazolones as selective non-hydroxamate inhibitors of tumor necrosis factor-α converting enzyme (TACE) [DOI]
  20. 20 Synthesis and anticonvulsant activity of 7-phenyl-6,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-ones and their derivatives [DOI]
  21. 21 Design, synthesis of 8-alkoxy-5,6-dihydro-[1,2,4]triazino[4,3-a]quinolin-1-ones with anticonvulsant activity [DOI]
  22. 22 New domino reaction. One pot synthesis of 4,7-dihydroxythioaurone derivatives from benzaldehydes and 4-acetyl-2-oxo-benz[1,3]oxathiole [DOI]
  23. 23 Design, synthesis and in vivo anticonvulsant screening in mice of Novel phenylacetamides [DOI]
  24. 24 New α, β and y semicarbazone and thiosemicarbazone 1,3-dithiolanes as radioprotectors. Anticonvulsant activity [DOI]
  25. 25 Synthesis and Reactivity of 3-Alkylthio-5-cyanomethyl-4-phenyl-1,2,4-triazoles [DOI]
  26. 26 Heterocyclic synthesis with isothiocyanates: An expeditious synthetic route for polyfunctionally substituted 3-(thiazol-2′-ylidene)pyridines and their fused derivatives [DOI]

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