Synthesis and Reactions of New Substituted Pyrimidine ThioneDerivatives as Antimicrobial Agents.-A variety of new pyrazolopyrimidinethiones bearing additional heterocyclic moieties are synthesized and evaluated for their antimicrobial activities. Some derivatives, e.g. (VI) and (VII), display significant to strong antimicrobial activity.-(ABD EL-GHAFFAR, NAHED F.; KASSAB, RAFIKA R. S.; SOLIMAN, FEKRIA M. A.; Rev.
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Reactions of 3-methyl-1-phenyl-4,6-dihydroimidazo[4,5-c]pyrazole-5(1H)-thione with carbonyl compounds gave the arylidene derivatives 2 and 3, with recinoleic acid, phosphorus oxychloride/phosphorus pentachloride mixture and copper bronze gave the adduct 4, the chloro derivative 5 and the dimer with desulfurization 7. The behaviour of the chloroderivative towards hydrazine and primary amines have also been studied. On the other, reaction of 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one with aromatic aldehydes gave the arylidene derivatives 8a-d, which on reaction with thiourea gave the pyrazolopyrimidinethione derivatives 9. The behaviour of compounds 9 towards copper bronze, sodium nitrite/acetic acid mixture, acrylonitrile and formaldehyde/ morpholine and its reaction with compound 1 in presence of copper bronze have also been taken into consideration.
Reaction of 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one with diazotized aromatic amines gave the corresponding diazenyl derivatives 1, which were condensed with carbonyl compounds to give the arylidene derivatives 2. Reaction of the parent pyrazolone with urea, thiourea and guanidine gave the pyrazoloimidazole derivatives 3. compound 3a reacted with thiourea in DMF to give the thiourea derivative 4. The reaction of 4 with malonic acid and acetyl chloride gave the pyrimidinedione derivative 5, which on reaction with thiourea in presence of sodium ethoxide gave the triazine derivative 6. S-alkylation of 6 with ethyl chloroacetate gave the ethyl acetate derivative 7, which on hydrolysis gave the corresponding acid, derivative8 and on reaction with hydrazine hydrate gave the corresponding acetohydrazide 9. the reaction of compound 9 with salicylaldehyde gave the pynazolidinone 10, while with carbon disulphide in alkaline solution it gave the oxadiazole thione 11 respectively. Some of the new compounds showed antimicrobial and antitumor activities.
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