Abstract
A new series of heterocycles incorporating antipyrine moiety were synthesized via reactions of 4-aminoantipyrine 1 with carbon disulphide then alkylation and /or chloroacetic acid to produce dithiocarbamate and rhodanine 3, 4 and 9. Multi-component reaction (MCR) of 4-aminoantipyrine with carbon disulfide and DMAD afforded rhodanine 7. The interaction of 9 with diazonium salt, DMF-DMA, nitrous acid and aromatic aldehydes to give thiazolidinone derivatives 10, 11, 13 and 14, respectively. Pyranothiazole 16 was prepared from reaction of 9 with cinamonitrile 15. Thiazolidinone 18 and thiazole 19 derivatives were obtained from reactions of 9 with phenyl isothiocyanate in the presence of KOH then halogenated the pot salt with ethyl bromoacetate and chloroacetone, respectively. Thiourea derivative 20 was prepared from reaction of methyl dithiocarbamate 3 with 4-aminoantipyrine. pyrimidine derivatives 21 and 22 were obtained from cyclocondensation of 3 with dimer of ethyl cyanoacetate and malononitrile. Pyrazolotriazine 24 was prepared from interaction of 3 with hydrazine hydrate. copounds 26 and 28 were obtained via reaction of 3 with glycine and anthranilic acid. Compounds 30, 32 and 34 were prepared via reaction of thiourea 20 with EAA, ECA and DMAD. Reaction of diazonium chloride of 1 with NaN3 afforded azide 36 which rearranged to triazine 39. The structures of the newly synthesized compounds were elucidated via elemental analysis and spectral data. The synthesized products were evaluated for their antimicrobial and anti-fungal activity.
Highlights
Antipyrine (1-phenyl-2,3-dimethylpyrazol-5-one) and its derivatives have been reported to possess varied biological activities such as analgesic [1,2], anti-inflammatory [3], antimicrobial [4-6], and anticancer activity [7], antiviral [8, 9], clinical [10], and pharmacological [11, 12] activities
The one-pot reaction of the antipyrine 1 with carbon disulfide and dimethyl acetylenedicarboxylate in ethanol at room temperature under stirring gave rhodanine derivative which identified as methyl 3-(1,5-dimethyl-3-oxo2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-4-oxo-2-thioxo-1,3-t hiazolidin- 5- ylidene] ethanoate (7)
Reaction of the potassium salt 2 with chloroacetone afforded thiazole derivative, which identified as 1,5-dimethyl-4-(4
Summary
Antipyrine (1-phenyl-2,3-dimethylpyrazol-5-one) and its derivatives have been reported to possess varied biological activities such as analgesic [1,2], anti-inflammatory [3], antimicrobial [4-6], and anticancer activity [7], antiviral [8, 9], clinical [10], and pharmacological [11, 12] activities. Rhodanine derivatives possess anticonvulsant, antibacterial, antiviral, and antidiabetic activities [13 - 15] Some of rhodanine-based derivatives act as hepatitis C virus (HCV) protease inhibitor [16]. The present work was demonstrated a strategy for the synthesis of novel rhodanine, thiazole, quinazolin-4-one, imidazolone and pyranothiazole bearing antipyrine moiety and investigated their antimicrobial potential activities
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