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Paper | Regular issue | Vol 92, No. 7, 2016, pp.1224-1243
Published online, 16th May, 2016
DOI: 10.3987/COM-16-13479
Prospective Study Directed to the Synthesis of Symmetrical Linked Bis-Rhodanine Derivatives with Their Antimicrobial Activity

Wael A. A. Arafa,* Raafat M. Shaker, and Saleh A. Rabeh

*Department Of Chemistry, Fayoum University, Fayoum 12975, Egypt

Abstract

One-pot three-component reactions of diamines, carbon disulfide and dialkyl acetylenedicarboxylates under conventional or ultrasound methods furnishing bis-rhodanines in good yields are described. Knoevenagel condensation reaction between 5,5’-methylene-bis-salicyaldehyde, pyrazole-3,5-dicarbaldehyde or terephthalaldehyde and N-alkylrhodanines afforded bis-arylidenerhodanines. While, the condensation between 2,6-diformylphenols and N-alkylrhodanines furnished only the mono-arylidenerhodanines. The newly synthesized compounds were characterized by HRMS and NMR spectral data. The compounds were screened for their in vitro antimicrobial activities. All the tested compounds showed pronounced activities, suggesting that the rhodanine moiety plays an important role in enhancing the antimicrobial properties of this class of compounds.