Synthesis and evaluation of ?-hydroxy fatty acid-derived heterocyclic compounds with potential industrial interest

Authors

  • A. M. F. Eissa Chemistry Department, Faculty of Science, Benha University
  • R. El-Sayed Chemistry Department, Faculty of Science, Benha University

DOI:

https://doi.org/10.3989/gya.2006.v57.i4.61

Keywords:

Antimicrobial properties, Heterocyclic derivatives, Physical properties, Surface active agents

Abstract


T2-Hydroxyheptadecanoic acid chloride (2) reacted with anthranilic acid to produce 2-substituted-3,1-benzoxazin-4-one (3) which was used as starting material to synthesize some condensed and non-condensed heterocyclic compounds by reaction with nitrogen nucleophiles e.g., hydrazine hydrate, and formamide. The products were subjected to reaction with different moles of propylene oxide (n = 5, 10, 15) to produce a novel group of nonionic compounds having a double function as antibacterial and surface active agents which can be used in the manufacturing of drugs, cosmetics, pesticides or can be used as antibacterial and/or antifungal additives. The surface active properties as surface and interfacial tension, cloud point, foaming height, wetting time, and emulsification power were determined, the antimicrobial and biodegradability were also screened.

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References

Aly, AA. 2003. Synthesis of novel quinazoline derivatives as antimicrobial agents. Chinese J. Chem. 21, 339- 346.

Amine MS, Eissa AMF, Shaaban AF, El-Sawy AA, El-Sayed R. 1998. Uses of quinazolin-2[(-propionoyl) isothiocyanate]-4-one as a building block in synthesis of some heterocyclic compounds of expected biological activity. Indian. J. Chem. 37B, 1153-1156.

Amine MS, Eissa AMF, Shaaban AF, El-Sawy AA, El- Sayed R. 1998. Utilization of 2-(2-carboxyethyl)-4(3H)- quinazolinethione in the synthesis of condensed and noncondensed heterocycles. Indian. J. Heterocycl. Chem. 7,4, 289-292.

Amine MS, Eissa AMF, Shaaban AF, El-Sawy AA, El- Sayed R. 2004. New heterocycles having double characters as antimicrobial and surface active agents. Part 3: Nonionic compounds from fatty acid hydrazide. Grasas Aceites 53, 124-128.

Amine 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, 370-377.

Cansiz A, Kaparir M, Demirdag A. 2004. Synthesis of some new 4,5-substituted-4H-1,2,4-trizole-3-thiol derivatives. Molecules 9, 204-212.

Draves CZ, Clarkso R. 1931. J. Am. Dye Stuff Reporter 20, 201.

Eissa AMF. 2003. Utilites of 2-ethyl-4H-3,1-benzoxazine- 4-one in synthesis of some interesting heterocyclic compounds. Chemistry: An Indian Journal 1, 17-21.

Eissa AMF, Ahmed, MHM. 2003. Nonionic surface active agents containing heterocyclic moieties. J. Olaj, Szappan, Kozmetika. 52, 11-17.

El-Sayed R, Wasfy AAF, Aly AA. 2005. Synthesis of novel heterocycles with antimicrobial and surface activity. J. Heterocyclic Chem. 42, 125-130.

El-Sukkary MA, El-Sawy AA, El-Dib. 1987. Synthetic Detergents from Crude rice bran oil. Hungarian J. Ind. Chem. 15, 317-320.

Eter ET, Richard RE, Darid, A. 1974. Biodegradable surfactants derived from corn starch. J. Am. Oil Chem. Soc. 51, 486-494. doi:10.1007/BF02635857

Findly A. 1963. Practical Physical Chemistry, 6th Ed., Longmans, London, p. 1040.

Madkour HMF. 2005. Reactivity of 4H-3,1-benzoxazin-4- ones towards nitrogen and carbon nucleophilic reagents: applications to the synthesis of new heterocycles. Arkat USA Inc. 4, 1-17.

Mohamed AS, Mohamed FA, Mohamed AA, Abdel- Basset, MS. 2003. Synthesis of novel 3H-quinazolin- 4-one containing pyrazolinone, pyrazole and pyrimidinone moieties. Molecules 8, 363-373.

Rosen MJ. 1989. 2th Ed., John Wiley & Sons, New York, pp. 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, 27-32.

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

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, 538-541. doi:10.1007/BF02822460

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Published

2006-12-31

How to Cite

1.
Eissa AMF, El-Sayed R. Synthesis and evaluation of ?-hydroxy fatty acid-derived heterocyclic compounds with potential industrial interest. Grasas aceites [Internet]. 2006Dec.31 [cited 2024Mar.28];57(4):367-75. Available from: https://grasasyaceites.revistas.csic.es/index.php/grasasyaceites/article/view/61

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Research