Abstract
Isoxazole, pyrazole, pyran, pyridine and pyrimidine derivatives of fatty acids were synthesized as surface and bioactive heterocycles. Hydroxylation of these intermediates by propylene oxide produced easy-to-handle, efficient and quickly biodegradable surface active agents, which revealed the importance of their applications in safety for humans as well as the environment. These compounds showed good activity against bacteria and fungi, showing promise in applications of drugs, cosmetics, and pesticides.
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Kale M, Patwardhan K. Synthesis of heterocyclic scaffolds with anti-hyperlipidemic potential: a review. Der Pharma Chemica. 2013;5(5):213–22.
Yusuf M, Jain P. Synthesis and biological significances of 1,3,4-thiadiazolines and related heterocyclic compounds. Arab J Chem. 2014;7(5):525–52.
Liu YT, Sun XM, Yin DW, Yuan F. Syntheses and biological activity of chalcones-imidazole derivatives. Res Chem Intermed. 2013;39:1037–48.
Albuquerque HMT, Santos CMM, Cavaleiro JAS, Silva AMS. Chalcones as versatile synthons for the synthesis of 5- and 6-membered nitrogen heterocycles. Curr Org Chem. 2014;18(21):2750–75.
Sortino M, Delgado P, Juárez S, Quiroga J, Abonía R, Insuasty B, Nogueras M, Rodero L, Garibotto FM, Enriz RD, Zacchino SA. Synthesis and antifungal activity of (Z)-5-arylidenerhodanines. Bioorg Med Chem. 2007;15:484–94.
Ghosh R, Das A. Synthesis and biological activities of chalcones and their heterocyclic derivatives: a review. World J Pharm Pharm Sci. 2014;3(3):578–95.
Cheng JH, Hung CF, Yang SC, Wang JP, Won SJ, Lin CN. Synthesis and cytotoxic, anti-inflammatory, and anti-oxidant activities of 2′, 5′-dialkoxylchalcones as cancer chemo-preventive agents. Bioorg Med Chem. 2008;16:7270–6.
Sankappa Rai U, Isloor AM, Shetty P, Pai KSR, Fun HK. Synthesis and in vitro biological evaluation of new pyrazole chalcones and heterocyclic diamides as potential anticancer agents. Arab J Chem. 2015;8:317–21.
Katsori AM, Hadjipavlou-Litina D. Chalcones in cancer: understanding their role in terms of QSAR. Curr Med Chem. 2009;16:1062–81.
Abdelhafez OM, Abdel-Latif NA, Badria FA. DNA, antiviral activities and cytotoxicity of new furochromone and benzofuran derivatives. Arch Pharm Res. 2011;34(10):1623–32.
Kalirajan R, Sivakumar SU, Jubie S, Gowramma B, Suresh B. Synthesis and biological evaluation of some heterocyclic derivatives of chalcones. Int J Chem Tech Res. 2009;1(1):27–34.
Al-Jamali NM. Preparation and bio-chemical identification of series organic compounds. J Chem Chem Sci. 2013;3(2):70–8.
Kandeel MM, Abdou NA, Kadry HH, El-Masry RM. Synthesis and antitumor activity of some novel heterocyclic compounds derived from chalcone analogues. Org Chem Ind J (OCAIJ). 2014;10(8):295–307.
Basri M, Abd Raman RNZR, Salleh AB. Specialty oleochemicals from palm oil via enzymatic synthesis. J Oil Palm Res. 2013;25:22–35.
Yıldırım A, Öztürk S, Çetin M. Long-chain alkylthia-benzimidazoles as corrosion inhibitors for carbon steel in H2SO4 solution. Phosphorus Sulfur Silicon. 2013;188(7):855–63.
Yadav S, Kumar P, DeClerq E, Balzarini J, Pannecouque C, Dewan SK, Narasimhan B. 4-[1-(Substituted aryl/alkyl carbonyl)-benzoimidazol-2-yl]-benzenesulfonic acids: synthesis, antimicrobial activity, QSAR studies, and antiviral evaluation. Eur J Med Chem. 2010;45:5985–97.
Jing L, Qiao W, Luo L, Peng H. Design and surface/interfacial properties of asymmetric triazine carboxyl betaine surfactants. J Surf Deterg. 2014;17:629–36.
El-Sayed R. Synthesis, antibacterial and surface activity of 1,2,4-triazole derivatives. Grasas Aceites. 2006;57(2):180–8.
El-Sayed R, Saleh AA. Utility of octadecyl amine in the synthesis of various nitrogen heterocycles: a preliminary investigation on their surface and biological activities. J Heterocycl Chem. 2016;53:1183–93.
Zielińska A, Nowak I. Fatty acids in vegetable oils and their importance in cosmetic industry. Chemik. 2014;68(2):103–10.
El-Sayed R, Saleh AA. Synthesis of some new thiazole, oxazole, pyrimidine and pyridazine derivatives from 2-cyano-N-octadecyl-acetamide as antimicrobial and surface active agents. J Heterocycl Chem. 2016;53:121–8.
El-Sayed R, Shaldom A, Al Mazrouee L. Synthesis and evaluation of poly-functionally substituted heterocyclic compounds derived from 2-cyano-n-(5-pentadecyl-1,3,4-thiadiazol-2-yl)acetamide. Synth Commun. 2015;45:886–97.
El-Sayed R. Substituted thiadiazole, oxadiazole, triazole and triazinone as antimicrobial and surface activity compounds. J Surf Deterg. 2013;16(1):39–47.
El-Sayed R, Asghar BH. Synthesis of various nitrogen heterocycles as antimicrobial surface agents. J Heterocycl Chem. 2014;51:1251–6.
El-Sayed R. Synthesis and heteroannulation of pyridine and related heterocyclic systems having surface and biological activities. J Oleo Sci. 2015;64(7):761–74.
El-Sayed R, Althagafi I. Potential biosignificant interest and surface activity of an efficient heterocyclic derivatives. J Oleo Sci. 2016;65:177–92.
El Sayed Aly MR, El Razek Abd, Fodah HH, Saleh SY. Antiobesity, antioxidant and cytotoxicity activities of newly synthesized chalcone derivatives and their metal complexes. Eur J Med Chem. 2014;76:517–53.
Morgós J, Sallay P, Farkas L, Rusznák I. Nitrogen containing compounds. J Am Oil Chem Soc. 1986;63:1209–10.
Findlay A. Practical physical chemistry. 6th ed. London: Longmans; 1935. p. 1040–69.
Weil JK, Stirton AJ, Nuñez-Ponzoa MV. Ether alcohol sulfates. The effect of oxypropylation and oxybutylation on surface active properties. J Am Oil Soc. 1966;43:603–6.
ASTM D1331–01. Standard test method for surface and interfacial tension of solutions of surface active agents. West Conshohocken: ASTM International; 2001.
Durham K. Properties of detergent solutions-amphipathy and adsorption, vol. 1. London: Surf Activity Deterg. MacMillan & Co., Ltd.; 1961. p. 1–28.
Draves CZ, Clarkson RG. A new method for the evaluation of wetting agents. J Am Dye Stuff Rep. 1931;20:201.
Ross J, Miles GD. Apparatus for comparison of foaming properties of soaps and detergents. Oil Soap. 1941;18:99–102.
Scholnick F, Linfield WM. Lactose-derived surfactants (III): fatty esters of oxy-alkylated lactitol. J Am Oil Chem Soc. 1977;54:430–5.
Throckmorton PE, Egan RR, Aelony D, Mulberry GK, Otey FH. Biodegradable surfactants derived from corn starch. J Am Oil Chem Soc. 1974;51:486–94.
National Committee for Clinical Laboratory Standards. Performance standards for antimicrobial disk susceptibility tests; approved standard M2-A8. Wayne: Clinical and Laboratory Standards Institute; 2003.
Kaushik NK, Kaushik N, Attri P, Kumar N, Kim CH, Verma AK, Choi EH. Biomedical importance of indoles. Molecules. 2013;18:6620–62.
Ren Y, Zhang L, Zhou CH, Geng RX. Recent development of benzotriazole-based medicinal drugs. Med Chem. 2014;4(9):640–62.
El-Sayed R, Khairou KS. Propoxylated fatty thiazole, pyrazole, triazole, and pyrrole derivatives with antimicrobial and surface activity. J Surf Deterg. 2015;18:661–73.
Negm NA, Badr EA, Zakaria K, Abd El-Raouf M. Environmentally friendly nonionic surfactants derived from jatropha oil fatty acids as inhibitors for carbon steel corrosion in acidic medium. J Surf Deterg. 2015;18(6):1011–24.
Negm NA, Ahmed SA, Badr EA, Ghani MA, Abd El-Raouf M. Synthesis and evaluation of nonionic surfactants derived from tannic acid as corrosion inhibitors for carbon steel in acidic medium. J Surf Deterg. 2015;18:989–1001.
Abd El-Ghaffar MA, Sherif MH, El-Habab AT. Synthesis, characterization, and evaluation of ethoxylated lauryl-myrisityl alcohol nonionic surfactants as wetting agents, anti-foamers, and minimum film forming temperature reducers in emulsion polymer lattices. J Surfact Deterg. 2017;20:117–28.
Myers D. Surfactant science and technology. 3rd ed. New York: John Wiley; 2006.
Ivanković T, Hrenović J. Surfactants in the environment. Arh Hig Rada Toksikol. 2010;61:95–110.
Shaker NO, Abd El-Salaam FH, El-Sadek BM, Kandeel EM, Baker SA. Anionic schiff base amphiphiles: synthesis, surface, biocidal and antitumor activities. J Am Sci. 2011;7(5):427–36.
Negm NA, El-Tabl AS, Aiad IA, Zakareya K, Moustafa AH. Synthesis, characterization, biodegradation and evaluation of the surface active properties of nonionic surfactants derived from Jatropha oil. J Surf Deterg. 2013;16:857–63.
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Howsaway, H.O., El-Sayed, R. Synthesis of Potential Pharmaceutical Heterocycles as Surface Active Agents. J Surfact Deterg 20, 681–694 (2017). https://doi.org/10.1007/s11743-017-1936-x
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DOI: https://doi.org/10.1007/s11743-017-1936-x