ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis and antimicrobial properties of new 2-((4-ethylphenoxy)methyl)benzoylthioureas

Carmen Limban, Alexandru V. Missir, Ileana C. Chirita, George M. Nitulescu, Miron T. Caproiu, and et al.

Pharmaceutical Chemistry Department, Faculty of Pharmacy, “Carol Davila”, University of Medicine and Pharmacy, Traian Vuia 6, Bucharest, 020956 Romania

E-mail: carmen_limban@yahoo.com

Abstract: New acylthiourea derivatives, 2-((4-ethylphenoxy)methyl)-N-(phenylcarbamothioyl)benzamides, were tested by qualitative and quantitative methods on various bacterial and fungal strains and proved to be active at low concentrations against Gram-positive and Gram-negative bacteria as well as fungi. These compounds were prepared by the reaction of 2-((4-ethylphenoxy)methyl)benzoyl isothiocyanate with various primary aromatic amines, and were characterised by melting point and solubility. The structures were identified by elemental analysis, ¹H and ¹³C NMR, and IR spectral data. The level of antimicrobial activity of the new 2-((4-ethylphenoxy)methyl)benzoylthiourea derivatives was dependent on the type, number and position of the substituent on the phenyl group attached to thiourea nitrogen. The iodine and nitro substituents favoured the antimicrobial activity against the Gram-negative bacterial strains, while the highest inhibitory effect against Gram-positive and fungal strains was exhibited by compounds with electron-donating substituents such as the methyl and ethyl groups.

Keywords: acylthiourea – 2-((4-ethylphenoxy)methyl)benzoic acid – ¹H NMR – ¹³C NMR – antimicrobial activity

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-010-0092-9

Chemical Papers 65 (1) 60–69 (2011)