29Oct 2017

USE OF 2-(1-(4-BROMOPHENYL) ETHYLIDENE)HYDRAZINECARBOTHIOAMIDE AND 2-(5-CHLORO-2-OXOINDOLIN-3-YLIDENE)HYDRAZINECARBOTHIOAMIDE IN THE SYNTHESES OF 2-THIOHYDANTOIN, PYRIMIDINE DERIVATIVES: EVALUATION OF THEIR ANTIMICROBIAL ACTIVITIES.

  • Department of Chemistry, Faculty of Applied Sciences, Umm Al-Qura University, Makkah, Saudi Arabia.
  • Department of Chemistry, Faculty of Science (Girl?s), Al-Azhar University, Cairo, Egypt.
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2-(1-(4-bromophenyl)ethylidene)hydrazinecarbothioamide 2a and 2-(5-chloro-2-oxoindolin-3-ylidene)hydrazinecarbothioamide 2b were used in the syntheses of new series of compounds. Acetylation of compounds 2a,b with acetic anhydride afforded acetyl derivatives 3a,b. Alkylation of 2b with ethyl iodide afforded the corresponding 2-(5-chloro-2-oxoindolin-3-ylidene)-N-ethylhydrazinecarbothioamide 4. Hydrazinolysis of 2a with hydrazine hydrate afforded 1,2-bis(1-(4-bromophenyl)ethylidene)hydrazine 5. Reaction of compounds 2a,b with ethyl acetoacetate and/or ethyl chloroacetate lead to the formation of 1-(1-(4-bromophenyl)ethylideneamino)-6-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one 6, 3-(1-(4-bromophenyl)ethylideneamino)-2-thioxoimidazolidin-4-one 7a and 5-chloro-3-(5-oxo-2-thioxoimidazolidin-1-ylimino)indolin-2-one 7b respectively. Condensation of compounds 7a,b with different aldehydes and ketones led to the formation of compounds 8a,b, 9 and 10. Acetylation of 7b with acetic anhydride under reflux gave N- acetyl derivative 11. Mannich base 12 was prepared by reaction of 7b with secondary amines such as di phenyl amine and formaldehyde in ethanol. Characterization of the synthesized compounds were done by IR, 1HNMR, 13CNMR, mass spectroscopy and elemental analysis. The antimicrobial activity was evaluated against Gram- positive bacteria: Staphylococcus aureus and Bacillus subtilis, Gram ? negative bacteria: Escherichia coli and Salmonella typhimurium, Yeast: Candida albicans and Fungus: Aspergillus fumigatusthe. The tested compounds recorded variable antimicrobial activities towards the used microorganism. Among the tested compounds, 9 showed the best activity against all the tested microorganisms.

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[Heba A. Elhady, Hameda S. Al-nathali and Refat El-Sayed. (2017); USE OF 2-(1-(4-BROMOPHENYL) ETHYLIDENE)HYDRAZINECARBOTHIOAMIDE AND 2-(5-CHLORO-2-OXOINDOLIN-3-YLIDENE)HYDRAZINECARBOTHIOAMIDE IN THE SYNTHESES OF 2-THIOHYDANTOIN, PYRIMIDINE DERIVATIVES: EVALUATION OF THEIR ANTIMICROBIAL ACTIVITIES. Int. J. of Adv. Res. 5 (Oct). 1716-1725] (ISSN 2320-5407). www.journalijar.com

Heba
Department of Chemistry, Faculty of Applied Sciences, Umm Al-Qura University, Makkah, Saudi Arabia

DOI:

Article DOI: 10.21474/IJAR01/5694      
DOI URL: https://dx.doi.org/10.21474/IJAR01/5694

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