Title: | Fatty Acids in Heterocyclic Synthesis.
Part XIV: Synthesis of Surface Active Agents from Some Novel Class of Oxadiazole, Thiadiazole and Triazole Derivatives Having Microbiological Activities. Journal of Surfactants and Detergents, (05/2014), 17(3): 509-523. |
Authors: | I. A. Gad El-Karim, M. S. Amine, A. A. Mahmoud, and A. S. Gouda |
Year: | 2014 |
Keywords: | Stearic acid, 2-Aminooxadiazole,Nonionic surfactant, Antimicrobial, Triazolo[3,4-b]oxadiazole, Imidazo[3,1-b]oxadiazole,Thiadiazole, Triazole, Surface properties. |
Journal: | Journal of Surfactants and Detergents |
Volume: | 17 |
Issue: | 3 |
Pages: | 509-523 |
Publisher: | Springer |
Local/International: | International |
Paper Link: | |
Full paper | Alaa Salah Gouda Mohamed Salem_onlinecopy-Oxadiazole_JSD.pdf |
Supplementary materials | Not Available |
Abstract: |
Reaction of stearic acid with semicarbazide in refluxing POCl3 afforded 2-amino-5-heptadecyl 1,3,4-oxadiazole. Acylation of the amino group with acetic anhydride, ethyl choloroacetate and chloroacetic acid gave amide and β-amino acid derivatives. These compounds were cyclized to imidazo[2,1-b]oxadiazole derivatives by two different techniques. Treating the starting oxadiazole compound with P2S5, hydroxyl amine and hydrazine hydrate in benzene afforded thiadiazole and triazole derivatives. Unexpectedly, triazolo[3,4-b][1,3,4]oxadiazole derivative was obtained when 1,3,4-oxadiazole derivative was refluxed with hydrazine hydrate in ethanol. The biological activities of the synthesized compounds were screened in vitro against some gram positive and gram negative bacteria and fungi. Addition of quantitative amount of propylene oxide units (3, 5, 7 moles) to the synthesized compounds afforded new nonionic surfactants. The physico-chemical and surface properties of the novel synthesized surfactants such as surface and interfacial tension, cloud point, wetting time, emulsion stability, foam height, CMC, resistance to hydrolysis and their biodegradability were investigated. In addition, surface parameters including effectiveness (πcmc), efficiency (PC20), maximum surface excess (Γmax) and (Amin) were examined. |