One-pot synthesis, theoretical study and antimicrobial activity of 5, 5′-(1, 4-phenylenebis-(methanylylidene))Bis(3-Aryl(Alkyl)-2-thioxoimidazolidin-4-one) derivatives. (1st February 2019)

• Record Type: Journal Article
• Authors: Shaker, Raafat M.; Abd El-Naby, Hisham A.; Ahmed, Essam Kh.; Ibrahim, Mahmoud A. A.; Gedamy, Sageda A.
• Is Part Of: Phosphorus, sulfur, and silicon and the related elements. Volume 194:Number 1/2(2019)
• Page Start: 147
• Page End: 155
• Publication Date: 2019-02-01
• Subjects: Bis-thiohydantoins -- terephthalaldehyde -- one-pot three-component reactions -- theoretical calculations -- antimicrobial activity; Sulfur compounds -- Periodicals; Organosulfur compounds -- Periodicals; Phosphorus compounds -- Periodicals; Organophosphorus compounds -- Periodicals; Silicon compounds -- Periodicals; Organosilicon compounds -- Periodicals; 546
• DOI: 10.1080/10426507.2018.1528256
• Languages: English
• ISSNs: 1042-6507

Abstract

Abstract: A simple, facile, and convenient practical method for the one-pot synthesis of pharmaceutically interesting 5, 5`-(1, 4-phenylenebis-(methanylylidene))bis-thiohydantoins via a three-component condensation reaction of terephthalaldehyde, α-amino acids and isothiocyanates had been developed. The S -alkylated derivatives 6a and 6b were obtained by the alkylation of the bis-thiohydantoins 4a with methyl iodide and/or benzyl chloride in a basic media. The molecular structures of the synthesized compounds were confirmed by their elemental analyses and spectral data (IR, 1 H, 13 C NMR and MS). The assignment of more stable Z - or E -isomers as the major form of 4a, 6a, and 8a was investigated by DFT calculations at B3LYP/6-31+G* level. Some of the prepared compounds were screened for their in-vitro antimicrobial activity. Compounds 4a, 6 b, 8 b and 8c exhibited low antibacterial activity against gram-positive bacteria Bacillus cereus . (5 Z, 5′ Z )-5, 5′-(1, 4-Phenylenebis(methanylylidene))bis(3-benzyl-2-thioxoimidazolidin-4-one) (4b ) exhibited good fungicidal activity against Fusarium oxysporum . Graphical Abstract: UF0001