Synthesis, antibacterial and surface activity of 1,2,4-triazole derivatives


  • R. El-Sayed Chemistry Department, Faculty of Science, Benha Unviversity



1, 2, 4-Triazol derivatives, Synthesis, Antibacterial properties, Surface activity properties


The use of sodium 1-(4-amino-5-mercapto-4H-[1,2,4] triazol-3-yl) and heptadecane-1-sulfonate (2) as new precursors to synthesize some important biologically active heterocycles has been found to be effective. The reaction of 2 with carbon disulphide in pyridine and acid chlorides yielded the 1,2,4-triazole derivatives 3, 4a and 4b.The condensation of 2 with appropriate aldehydes gave 5a-c which were cyclized by treating with thioglycollic acid to yield 6a-c. The reactions of 2 with phthalic anhydride and 4-methylbenzene-sulfonylchloride gave 7 and 8. In addition, the reaction of 2 with chloroacetaldehyde, phenacyl bromide, urea and chloroacetyl chloride yielded 9, 10, 11 and 12. At the same time, refluxing 2 with phenyl isothiocyanate gave 13 and 14. All these products have antimicrobial activity and they can be used as surface active agents.


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Amin M. S., Eissa A. M. F., Shaaban A. F., El-Sawy A. A., 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.

Amin M. S., Eissa A. M. F., Shaaban A. F., El-Sawy A. A., El-Sayed R. 2003. New heterocycles having a double characters;as antimicrobial and surface active agents. Part 2: Anionic compounds from fatty acid isothiocyanate. J. Chemistry: An Indian Journal, 1, 313-319.

Boshra M. A., Ferwanah A. S., Awadallah A. M., El-Halabi N. M. 2002. Reaction of nitrilimines with ketoalkoxycarbonyl- hydrazones: Synthesis of substituted 1,2,4-triazoles and heterocyclic spiro compounds. Asian J. Chem. 14, 1235-1240.

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

Eissa A. M. F. 2002. Anionic surface active agents from fatty acid hydrazides containing heterocyclic moiety. J. Olaj, Szappan, Kozmetika, 51, 155-161.

Eissa A. M. F., Ahmed M. H. M. 2003. Nonionic surface active agents containing heterocyclic moiety. J. Olaj, Szappan, Kozmetika 52,11-17.

El-Sayed R., Wasfy A. A. F., Aly A. A. 2005. Synthysis of novel heterocycles with antimicrobial and surface active agents. J. Heterocyclic Chem. 42, 1-6.

El-Sukkary M. A., El-Sawy A. A., El-Dib. 1987. Synthetic detergents from crude rice bran oil. Hung. J. Industrial Chem. 15, 317-320.

Eter E. T., Richard R. E., 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.

Hovsepian T. R., Dilanian E. R., Engoyan A. P., Melik- Ohanjaian R. G. 2004. Synthesis of substituted 1,2,4- triazoles and 1,3,4-thiadiazole. J. Chem. Heterocyclic Compounds 40 1194-1198. doi:10.1023/B:COHC.0000048294.27172.a3

Katica C., Vesna D., Vlado K., Dora G. M., Aleksandra B. 2001. Synthesis, antibacterial and antifungal activity of 4-substituted-5-aryl-1,2,4-triazoles. Molecules 6, 815-824.

Kumar P. S., Nagoji K. E. V., Ravikum B.V.V. 2003. Synthesis of 3-ethoxycarbonyl-5-phenyl-1- p-tolyl- 1,2,4-triazolo[3,4,-c]1,2,4-triazole. Asian J. Chem. 15, 515-518.

Li-Xue Z., An-Jian Z., Xian-Xin C., Xin-Xiang L., Xiang- Yun N., Dong-Yung C., Zhang Z. 2002. Synthesis and biological activity of 3-(2-furanyl)-6-aryl-1,2,4- triazolo[3,4-b]-1,3,4-thiadiazoles. Molecules 7, 681- 689.

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

Oganisyan A. Sh., Noravyan A. S., Grigoryan M. Zh. 2004. Condensed pyrido-pyrimidines. 7. Synthesis of condensed triazolo[4,3-c]- and tetrazolo[1,5-] pyrimidnes. Chem. Heterocyclic Compounds 40, 75-78. doi:10.1023/B:COHC.0000023771.49658.46

Somaya A. R., Eissa A. M. F., Nadia. A., Ahmad, M. N. 1998. Synthesis and characterization of some peptides having surface activity using polyethylene glycol. J. Pharm. Sci. 7, 27-32.

Stankovsk S., Spirkov K. 2000. Reaction of imidoyl and amidinoyl isothiocyanates with some C-acid salts. Chem. Papers 54, 36-38.

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

Tayseer A. A., Manal A. D., Hamdi M. H. 2002. A novel synthesis of 1, 2,4-triazolopteridines. Molecules 7, 494-500.

Walid M. F., Pazdera P. 2002. Synthesis of heterocyclic skeletons by the reaction of N1-(2-cyanophenyl)- benzimidoyl chloride with thioamides. Molecules 7, 96-103.

Wasfy A. A. F. 2003. Fused heterocycles. Part 1. Synthesis of some annelated 1,2,4-triazole system from [4-(1H-benzimidazol-2-yl)-phthalazin-1- yl)hydrazine. J. Chem. Res. 8, 457-458.

Wiel J. K., Smith F. D., Stirton A. J., Bistine R. G. Jr. 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

Xin-Ping H., Heng-Shan D., Peng-Fei X., Zhang Z., Qin W., Yan-Ni G. 2000. Heterocyclic systems containing bridged nitrogen atoms synthesis and antibacterial activity of 3-(2-phenylquinolin-4-yl)/3-(1-p-chlorophenyl- 5-methyl-1,2,3-triazol-4-yl)-s-triazolo[3,4-b]-1,3,4- thiadiazine derivatives, J. Chinese Chem. Soc. 47, 1115-1119.




How to Cite

El-Sayed R. Synthesis, antibacterial and surface activity of 1,2,4-triazole derivatives. Grasas aceites [Internet]. 2006Jun.30 [cited 2024May23];57(2):180-8. Available from: