Síntesis y propiedades antibacterianas y tensoactivas de derivados 1,2,4-triazólicos

Autores/as

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

DOI:

https://doi.org/10.3989/gya.2006.v57.i2.35

Palabras clave:

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

Resumen


Es interesante el uso del 1-(4-amino-5-mercapto-4H- [1,2,4]triazol-3-il)heptadecano-1-sulfonato sódico (2) como un nuevo precursor en la síntesis de compuestos heterocíclicos biológicamente importantes. La reacción de 2 con disulfuro de carbono en piridina y cloruros de acilo rindió derivados 1,2,4-triazólicos. Condensación de 2 con aldehídos apropiados produjo 5a-c que ciclaron por tratamiento con ácido tioglicólico para dar lugar a 6a-c. Reacciones de 2 con anhídrido ftálico y cloruro de 4-metilbenzenosulfonilo produjeron 7 y 8. Además, la reacción de 2 con cloroacetaldehído, bromuro de fenacilo, urea, cloruro de tiacetilo produjo 9, 10, 11, y 12. Por otra parte, el reflujo de 2 con isocianato de fenilo dio 13 y 14. Todos los productos tuvieron actividad antimicrobiana y propiedades tensoactivas.

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Citas

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.

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Publicado

2006-06-30

Cómo citar

1.
El-Sayed R. Síntesis y propiedades antibacterianas y tensoactivas de derivados 1,2,4-triazólicos. Grasas aceites [Internet]. 30 de junio de 2006 [citado 2 de mayo de 2025];57(2):180-8. Disponible en: https://grasasyaceites.revistas.csic.es/index.php/grasasyaceites/article/view/35

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Investigación