Synthesis and antimicrobial evaluation of new glucosylimino thiazole derivatives

• Published in: Journal of the Iranian Chemical Society Vol. 16; no. 7; pp. 1391 - 1399
• Main Authors: Ghoneim, Amira A., El-Farargy, Ahmed F.
• Format: Journal Article
• Language: English
• Published: Berlin/Heidelberg Springer Berlin Heidelberg 01.07.2019; Springer Nature B.V
• Subjects: Analytical Chemistry; Aniline; Biochemistry; Chemical synthesis; Chemistry; Chemistry and Materials Science; E coli; Fungicides; Inorganic Chemistry; Organic Chemistry; Original Paper; Physical Chemistry; Propionic acid; Thiourea derivatives; Thioureas; Antimicrobial; Synthesis; Glucosylimino; Thiazole derivatives
• ISSN: 1735-207X; 1735-2428
• DOI: 10.1007/s13738-019-01617-2

p -Sulphonic- N -propionyl aniline 3 was produced from sulphanilic acid with propionic acid under reflux for 2 h, then the compound 3 reacted with thionyl chloride and the corresponding imidoyl chloride 4 was obtained. When imidoyl chloride 4 reacted with potassium isothiocyanate and aniline, the corresponding thiourea derivatives 6 was produced. Compound 6 was reacted with tricyanovinylamine to produce the thiazole derivative 7 after cyclization. The microwave-assisted condensation of 2,3,4.6,-tetra- O -acetyl- β - D -glucopyranosylisothiocynate 8 with thiazole derivative 7 afforded the thiourea derivatives 9 . Compound 10 a, b has been synthesized by reacting thiourea derivatives 9 with chloroacetone. The prepared compounds were screened for antibacterial properties against Staphylococcus aureus and Escherichia coli , and antifungal activity against Candida sp. The structure assignments of the new synthesized compounds are based on spectroscopic data.