Synthesis and Biological Activities of New 1,2,4-Triazol-3-one Derivatives

Abstract

New 2-phenacyl-1,2,4-triazol-3-ones were obtained by the reaction of 5-alkyl-1,2,4-triazol-3-ones with alpha-bromoacetophenone in alkaline medium. Selective reduction of the side chain carbonyl group to hydroxy group was achieved with NaBH4. The reaction of some compounds containing a phenolic hydroxyl with 4-toluenesulfonyl chloride or benzyl bromide in the presence of NaOH led to tosylated or benzylated derivatives. The tosylation or benzylation at the alcoholic hydroxyl was carried out in the presence of sodium metal. Some of the newly synthesized compounds revealed an antimicrobial activity; 6 of 14 new compounds that were studied by the National Cancer Institute were found to possess antitumor activity.

Synthesis of New Bis-1,2,4-Triazole Derivatives

“…For example, fluconazole is used as an antimicrobial drug [17], while vorozole, letrozole and anastrozole are non-steroidal drugs used for the threatment of cancer [18] and loreclezole is used as an anticonvulsant [19]. Furthermore, in recent years some Schiff base derivatives of 1,2,4-triazoles and their reduced derivatives have been also found to possess pharmacological activities [20][21][22][23][24][25][26]. These biological data prompted us to synthesize some new bis-1,2,4-triazole derivatives, and in the present study, a novel series of bis-Schiff base derivatives resulting from the reaction of 4-amino-3-aryl-5-phenyl-4H-1,2,4-triazoles 3 with bis-aldehydes 1 and their corresponding reduced derivatives were synthesized and characterized by IR, 1 H-NMR, 13 C-NMR and mass spectral data.…”

Antimicrobial and cytotoxic activities of 1,2,3-triazole-sucrose derivatives

“…39 been attributed to the presence of triazole ring system; one of the major examples containing triazole ring is fluconazole. 8 According to the obtained results, it is obvious that the derivatives 5 (with 4-pentylphenyl substituent) showed the best antibacterial activity, while 3 (with 4-bromophenyl substituent) possessed the best antifungal activity.…”

“…7 New triazoles with improved pharmacological and pharmacokinetic profiles are emerging rapidly. 8 Various glycosides can be found in natural resources, mainly in the form of glycoconjugates, such as glycopeptides, glycolipids, and nucleic acids, where the saccharide moiety plays important role for their biological activity. 9 Considering that sugar moieties with polyhydroxyl groups have been extensively employed in drug design with the view to improve water solubility and to increase the interaction between receptors and guests for molecular recognition, 10,11 various novel monosaccharide-derived 1,2,3-triazoles were synthesized and their inhibiting activities for glycosidases, such as α-glucosidase, isomaltase, amyloglucosidase and β-glucosidase, 12 sweet almond β-glucosidase and yeast α-glucosidase, 13 or a-glucosidase (Saccharomyces cerevisiae), β-glucosidase (almonds), α-galactosidase (green coffee beans), β-galactosidase (Aspergillus oryzae), α-mannosidase (Canavalia ensiformis), β-mannosidase (snail acetone powder), and β-N-acetylglucosaminidase, 14 were tested.…”

Synthesis and Biological Activities of 3-Alkyl-5-substituted 1,2,4-Triazole Derivatives

“…Azoles are the prominent type of compounds used for this purpose. 1,2,4,-Triazole and its derivatives are an important class of nitrogenous heterocyclic compounds which has been shown to possess a wide range of pharmacological properties such as antifungal 2,3 , antibacterial 4,5 , antimalarial 6 , antiinflammatory, anticonvulsant, antidepressant, antiviral and antitumor activities [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] . Therefore, 1,2,4-triazole derivatives have attracted considerable attention during the last few decades [22][23][24][25] .…”