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.

Downloads

Download data is not yet available.

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

Downloads

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. grasasaceites [Internet]. 2006Dec.31 [cited 2021Dec.5];57(4):367-75. Available from: https://grasasyaceites.revistas.csic.es/index.php/grasasyaceites/article/view/61

Issue

Section

Research