2-Hydroxyphenacyl azoles and related azolium derivatives as antifungal agents

Emami, Saeed; Foroumadi, Alireza; Falahati, Mehraban; Lotfali, Ensieh; Rajabalian, Saeed; Ebrahimi, Soltan-Ahmed; Farahyar, Shirin; Shafiee, Abbas

doi:10.1016/j.bmcl.2007.10.111

Cited by 93 publications

(66 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For example, 1H-1,2,4-triazole could react with the highly reactive -bromoketone 202 to provide the N-alkylated product, and subsequently underwent Nquaternization of 1,2,4-triazole ring to successfully give triazolium 203 in 49% yield. Bioactivity screening found that mono-triazolium bromide 203 gave excellent antimicrobial activities with broad bioactive spectrum, and its anti-Saccharomyces cerevisiae activity was 8-fold more potent than that of reference drug Fluconazole (MIC = 32 g/mL) (Scheme 88) [278]. Naphthalimides with strong hydrophobicity and desirable large -conjugated backbone could easily interact with various active sites in biological system via non-covalent forces to exhibit diversely biological activities.…”

Section: N-quaternization Of 124-triazole Ringmentioning

confidence: 99%

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Zhang¹,

Damu²,

Cai³

et al. 2014

COC

View full text Add to dashboard Cite

Heterocyclic 1,2,4-triazole derivatives possess unusually spacious potentiality as medicinal agents, agricultural chemicals, functional materials, ionic liquids, supramolecular catalysts as well as artificial enzymes and receptors for supramolecular recognition and biomimetic catalysis, and their various researches and developments have been being a quite rapidly developing and active highlight topic with an infinite space. Numerous efforts have been directed toward various types of possible applications of 1,2,4-triazole-based compounds and a lot of important progress has been made, especially their preparations have attracted increasing attention. This review systematically summarized the recent advances in the syntheses of 1,2,4-triazole derivatives, including: (1) Cyclizations to form triazole ring; (2) Transformations of heterocyclic compounds to construct triazole ring; (3) Substitutions on 1,2,4-triazole ring; (4) Structural modifications in side chains of 1,2,4-triazole ring. It was hoped that this review would be helpful for the design and development of highly efficient preparation of 1,2,4-triazole derivatives with various sorts and varieties of extensively potential applications in medicine, agriculture, chemistry, materials, supramolecular sciences and so on.

show abstract

Section: N-quaternization Of 124-triazole Ringmentioning

confidence: 99%

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Zhang¹,

Damu²,

Cai³

et al. 2014

COC

View full text Add to dashboard Cite

show abstract

“…The 1-(2-hydroxyphenyl)-2-(1H-imidazol-1-yl)ethanone (2) and trans-2,3-dihydro-3-(1H-imidazol-1-yl)-2-methyl-4H-1-benzopyran-4-one (4a) were prepared according to the literature methods 11,12 . The progress of reactions and the purity of compounds were checked by a thin-layer chromatography using Merck silica gel 60 F254 plates (Darmstadt, Germany), and visualization was achieved with UV light (254 nm).…”

Section: Chemistrymentioning

confidence: 99%

Imidazolylchromanones containing alkyl side chain as lanosterol 14α-demethylase inhibitors: synthesis, antifungal activity and docking study

Emami

Banipoulad

Irannejad

et al. 2013

Journal of Enzyme Inhibition and Medicinal Chemistry

Self Cite

View full text Add to dashboard Cite

Previously, 2-alkylchromans have been introduced as non-azole inhibitors of 14a-demethylase. Accordingly, we incorporated imidazole ring on the 3-position of 2-alkylchromanones to design new inhibitors of 14a-demethylase and potential antifungal agents. Thus, a series of 2-alkyl-3-imidazolylchromanones were synthesized starting from 2-hydroxyphenacyl bromide. The transconfiguration of compounds was confirmed by NMR-spectroscopy. The antifungal activity of title compounds were evaluated against different fungi in comparison with fluconazole and miconazole. trans-2-(1-Pentyl)-3-imidazolylchroman-4-one (4d) showed the most potent activity against yeasts comparable to fluconazole. The experimental data based on 1 H NMR spectroscopy revealed that 2-alkyl side chain and 3-imidazolyl moiety in compound 4d exist predominantly in the di-equatorial conformation. While docking study with 14a-demethylase demonstrated that the di-axial form of compound 4d can be considered as active conformation.

show abstract

“…Very recently, it was reported in the literature that 2-hydroxyphenacyl triazolium derivatives (2a -2f, Fig. 2) exhibited significant antifungal activities [15]. In addition, many investigations could show that the introduction of variable aromatic and aliphatic substituents could markedly affect the biological activities of triazole derivatives, especially some halogen-substituted aromatic compounds such as 2,4-dichlorobenzyl, 2,4-difluorobenzyl ones, were found to be biologically important and could improve the antimicrobial activities [16,17].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antibacterial and Antifungal Activities of Novel 1,2,4‐Triazolium Derivatives

Luo

Gan

et al. 2009

Archiv der Pharmazie

View full text Add to dashboard Cite

A series of novel 1,2,4-triazolium derivatives was synthesized starting from commercially available 1H-1,2,4-triazole, 2,4-dichlorobenzyl chloride, or 2,4-difluorobenzyl bromide. Their antibacterial and antifungal activities were evaluated against Staphylococcus aureus ATCC 29213, Escherichia coli ATCC 25922, Bacillus proteus, Bacillus subtilis, Pseudomonas aeruginosa, Candida albicans ATCC 76615, and Aspergillus fumigatus. All structures of the new compounds were confirmed by NMR, IR, and MS spectra, and elemental analyses. The antimicrobial tests showed that most of synthesized triazolium derivatives exhibit significant antibacterial and antifungal activities in vitro. 1-(2,4-Difluorobenzyl)-4-dodecyl-1H-1,2,4-triazol-4-ium bromide and 1-(2,4-Dichlorobenzyl)-4-dodecyl-1H-1,2,4- triazol-4-ium bromide were the most potent compounds against all tested strains with the MIC values ranging from 1.05 to 8.38 microM. They exhibited much stronger activities than the standard drugs chloramphenicol and fluconazole which are in clinical use. The results also showed that the antimicrobial activities of triazolium derivatives depend upon the type of substituent, the length of the alkyl chain, and the number of triazolium rings.

show abstract

2-Hydroxyphenacyl azoles and related azolium derivatives as antifungal agents

Cited by 93 publications

References 17 publications

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Imidazolylchromanones containing alkyl side chain as lanosterol 14α-demethylase inhibitors: synthesis, antifungal activity and docking study

Synthesis, Antibacterial and Antifungal Activities of Novel 1,2,4‐Triazolium Derivatives

Contact Info

Product

Resources

About