Surface active properties and biological activity of novel nonionic surfactants containing pyrimidines and related nitrogen heterocyclic ring systems
DOI:
https://doi.org/10.3989/gya.2008.v59.i2.498Keywords:
Antimicrobial activity, Surface activity, SynthesisAbstract
A series of annelated pyrimidine derivatives has been synthesized via different heterocyclization reactions of suitably functionalized 6-(4-octadecyloxyphenyl)-4-oxo-2- thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile (4) with different electrophiles and nucleophiles. These heterocycles bear an active hydrogen atom (NH, OH or COOH) which could be propoxylated using propylene oxide with different moles, 5, 10 and 15, to produce nonionic surfactant having a long alkyl chain with molecular weight suitable for becoming an amphiphilic molecule with correct hydrophilic-lypophilic balance which enhances solubility, biodegradability and hence lowers the toxicity to human beings and becomes environmentally friendly. In addition, the antimicrobial activities of these compounds were screened and it was found that some of these compounds have similar or higher activity compared with commercial antibiotic drugs (sulphadiazine), which make them suitable for diverse applications like the manufacturing of drugs, pesticides, emulsifiers, cosmetics, etc.
Downloads
References
Ahmed MHM. 2004. Preparation and surface active properties of novel succinic acid based surfactants. Olaj, Szappan, Kozmetika. 53 (1) 23-26.
Aly AA. 2005. A Convenient synthesis and pharmacological activity of novel annulated pyrimidine derivatives. Chinese. J . Chem. 23 (2) 1-5. doi:10.1002/cjoc.200590211
Aly AA, Nassar SA. 2004. N-[4-(dicyanomethylazo) phenyl]-2-saccharin-2-ylacetamide in the synthesis of pyridazine and pyrimidine derivatives. Heteroatom Chem. 15 (1) 1-4. doi:10.1002/hc.10194
Amin MS, Eissa AMF, Shaaban AF, El-Sawy AA, El-Sayed R. 2004. New heterocycles having a double characters; as antimicrobial and surface active agents. Part 1: Nonionic compounds from fatty acid isothiocyanate. Grasas Aceites 55 (4) 370-376.
Amin MS, Aly AA, El-Sayed R. 2006. Synthesis and surface active properties of quinazoline derivatives of industrial application. Ind. J. Chem. 45B, 1020.
Chaudlhuri RK, Login RB, Tracy D J. 1987. U.S. Patent. 4, 463-468.
Eissa AMF, El-Sayed R. 2006. Synthesis and evaluation of condensed and noncondensed heterocyclic compounds of industrial application. J. Heterocyclic Chem. 43, 1-9.
Amin MS, Hebash KA, Ahmed MHM, El-Sheikh AA. 2006. New heterocycles having double characters as antimicrobial and as surface active agents. Part 5:New quinazoline derivatives from stearic acid. Olaj, Szappan, Kozmetika 55 (4) 126 121
Draves CZ. Clarkso R. 1931., J. Am. Dye Stuff Reporter 20, 201.
El-Sayed R, Wasfy AAF, Aly AA. 2005. Synthesis of novel heterocycles with antimicrobial and surface Activity. J. Heterocyclic Chem. 42 (1) 1-6.
El-Sayed R. 2006. Synthesis, antibacterial and surface activity of 1,2,4-triazole derivatives. Grasas Aceites. 57 (2) 180-188.
El-Dougdoug WIA, Ahmed MHM. 2004. Synthesis and surface active properties of gawafa fats based amphoteric surfactants. Olaj, Szappan, Kozmetika. 53 (2) 63-68.
El-Sawy AA, Essawy SA, El-Sukkary MM, Eissa AMF. 1992. Surfactants from 2-hydroxy fatty acids. Hungarian Journal of Industerial chemistry. 20, 25.
El-Sukkary MA, El-Sawy AA, El-Dib F. 1987. Synthetic Detergents from Crude rice bran oil. Hungarian Journal of Industrial Chemistry 15, 317-322.
Eman AE, Mohamed AK. 2004. 2-Cyanoacetamide in the synthesis of heterocyclic compounds: Synthesis of new polysubstituted pyrazole, pyridine and pyramimidine derivatives. J. Chinese Chem. Soc. 51, 779-784.
Eter ET, Richard RE, Darid A. 1974. Biodegradable surfactants derived from corn starch. J. Am. Oil Chem. Soc. 51, 486-491. doi:10.1007/BF02635857
Findly A. 1963. Practical Physical Chemistry. Longmans, London., 6th Ed.1040.
Gean VS, Ademir N, Evandro LD, César Z. 2001. Preparation of aromatic esters and dioxolanes under microwave irradiation. Synthetic Communications 31, 3323 doi:10.1081/SCC-100106043
Maisa IA, Ahmed AG, Galal ME, Soliman MM. 2004. Synthesis of new furo[2,3-d]pyrimidine and pyrimido[4`,5`:4,5]furo[2,3-d]pyrimidines., J. Chinese Chem. Soc. 51, 1357-1366.
Masuyama A, Akiyama K, Okahara M. 1987. Surface active hydroxamic acid. II. Comparison of surface properties of hydroxamic acids with ketones and methyl esters with similar hydrophilic and lipophilic structure. J. Am. Oil. Chem. Soc. 64, 1040-1043. doi:10.1007/BF02542446
Morgos J, Sallay P, Farkas L, Rus Znar I. 1983. J. Am. Oil Chem. Soc. 60, 11. doi:10.1007/BF02901549
Rosen MJ. 1989. Surfactants and interfacial phenomena. 2th Ed., John Wiley & Sons, New York, 286-294.
Somaya AR, Eissa AMF, Nadia A, Ahmad MN. 1998. Synthesis and characterization of some peptides having surface activity using polyethylene glycol. J. Pharm. Sci. 7, 27.
Takeshi H. 1970. Studies of ester containing surfactant: Preparation and properties of sodium sulphalkanoates. Bull. Chem. Soc. 43, 2236-2239. doi:10.1246/bcsj.43.2236
Xu LZ, Jian FF, Shi JG, Li L. 2004. Synthesis, structure and biological activities of novel triazole compounds containing 4,6-dimethyl-pyrimidine-2-thio group., J. Chinese Chem. Soc. 22, 1308-1312.
Wanchai P, Warinthorn C. 2006. An efficient method for chlorination of alcohols using PPh3/ Cl3CCONH2. Tetrahedron Letters 47, 6821 doi:10.1016/j.tetlet.2006.07.060
Wiel JK, Smith FD, Stirton AJ, Bistine RG. 1963. Long chain alkanesulphonates and 1-hydroxy-2- alkanesulphonates: Structure and property relations. J. Am. Oil. Chem. Soc. 40, 538-542. doi:10.1007/BF02822460
Yvette AI, Aly AA. 2003. A convenient synthesis of new pentaazacyclopentanaphthalene and pentaazaphenanthrene derivatives. Z. Naturforsch. 58b, 1227.
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2008 Consejo Superior de Investigaciones Científicas (CSIC)
This work is licensed under a Creative Commons Attribution 4.0 International License.
© CSIC. Manuscripts published in both the printed and online versions of this Journal are the property of Consejo Superior de Investigaciones Científicas, and quoting this source is a requirement for any partial or full reproduction.All contents of this electronic edition, except where otherwise noted, are distributed under a “Creative Commons Attribution 4.0 International” (CC BY 4.0) License. You may read here the basic information and the legal text of the license. The indication of the CC BY 4.0 License must be expressly stated in this way when necessary.
Self-archiving in repositories, personal webpages or similar, of any version other than the published by the Editor, is not allowed.
