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Design, synthesis, and antifungal activities of novel triazole derivatives containing the benzyl group.

Xu K, Huang L, Xu Z, Wang Y, Bai G, Wu Q, Wang X, Yu S, Jiang Y - Drug Des Devel Ther (2015)

Bottom Line: In previous studies undertaken by our group, a series of 1-(1H-1,2,4-triazole-1-yl)-2-(2,4-difluorophenyl)-3-substituted-2-propanols (1a-r), which were analogs of fluconazole, was designed and synthesized by click chemistry.In the study reported here, the in vitro antifungal activities of all the target compounds were evaluated against eight human pathogenic fungi.Compounds 1a, 1q, and 1r showed the more antifungal activity than the others.

View Article: PubMed Central - PubMed

Affiliation: School of Pharmacy, Second Military Medical University, Shanghai, People's Republic of China.

ABSTRACT
In previous studies undertaken by our group, a series of 1-(1H-1,2,4-triazole-1-yl)-2-(2,4-difluorophenyl)-3-substituted-2-propanols (1a-r), which were analogs of fluconazole, was designed and synthesized by click chemistry. In the study reported here, the in vitro antifungal activities of all the target compounds were evaluated against eight human pathogenic fungi. Compounds 1a, 1q, and 1r showed the more antifungal activity than the others.

No MeSH data available.


Related in: MedlinePlus

Synthesis of the target compounds 1a–r.Notes: Conditions: (a) Et3N, benzylamine, EtOH, Et3N, reflux, 5 hours, 72%; (b) propargyl bromide, KI, K2CO3, CH3CN, rt, 5–6 hours, 81%; (c) NaN3, substituted benzyl bromide, dimethyl sulfoxide, CuSO4·5H2O, sodium ascorbate, rt, 12 hours, 60%–70%.
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f3-dddt-9-1459: Synthesis of the target compounds 1a–r.Notes: Conditions: (a) Et3N, benzylamine, EtOH, Et3N, reflux, 5 hours, 72%; (b) propargyl bromide, KI, K2CO3, CH3CN, rt, 5–6 hours, 81%; (c) NaN3, substituted benzyl bromide, dimethyl sulfoxide, CuSO4·5H2O, sodium ascorbate, rt, 12 hours, 60%–70%.

Mentions: The general synthetic methodology for the preparation of the title compounds (1a–r) is outlined in Figure 3. Compound 3 was synthesized by ring-open reaction of oxirane 2 with benzylamine. Then, compound 3 was transformed into compound 4 by reacting with propargyl bromide in the presence of KI and K2CO3 in acetonitrile. The target compounds were obtained by using click chemistry28 with various substituted benzyl azides.


Design, synthesis, and antifungal activities of novel triazole derivatives containing the benzyl group.

Xu K, Huang L, Xu Z, Wang Y, Bai G, Wu Q, Wang X, Yu S, Jiang Y - Drug Des Devel Ther (2015)

Synthesis of the target compounds 1a–r.Notes: Conditions: (a) Et3N, benzylamine, EtOH, Et3N, reflux, 5 hours, 72%; (b) propargyl bromide, KI, K2CO3, CH3CN, rt, 5–6 hours, 81%; (c) NaN3, substituted benzyl bromide, dimethyl sulfoxide, CuSO4·5H2O, sodium ascorbate, rt, 12 hours, 60%–70%.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4362653&req=5

f3-dddt-9-1459: Synthesis of the target compounds 1a–r.Notes: Conditions: (a) Et3N, benzylamine, EtOH, Et3N, reflux, 5 hours, 72%; (b) propargyl bromide, KI, K2CO3, CH3CN, rt, 5–6 hours, 81%; (c) NaN3, substituted benzyl bromide, dimethyl sulfoxide, CuSO4·5H2O, sodium ascorbate, rt, 12 hours, 60%–70%.
Mentions: The general synthetic methodology for the preparation of the title compounds (1a–r) is outlined in Figure 3. Compound 3 was synthesized by ring-open reaction of oxirane 2 with benzylamine. Then, compound 3 was transformed into compound 4 by reacting with propargyl bromide in the presence of KI and K2CO3 in acetonitrile. The target compounds were obtained by using click chemistry28 with various substituted benzyl azides.

Bottom Line: In previous studies undertaken by our group, a series of 1-(1H-1,2,4-triazole-1-yl)-2-(2,4-difluorophenyl)-3-substituted-2-propanols (1a-r), which were analogs of fluconazole, was designed and synthesized by click chemistry.In the study reported here, the in vitro antifungal activities of all the target compounds were evaluated against eight human pathogenic fungi.Compounds 1a, 1q, and 1r showed the more antifungal activity than the others.

View Article: PubMed Central - PubMed

Affiliation: School of Pharmacy, Second Military Medical University, Shanghai, People's Republic of China.

ABSTRACT
In previous studies undertaken by our group, a series of 1-(1H-1,2,4-triazole-1-yl)-2-(2,4-difluorophenyl)-3-substituted-2-propanols (1a-r), which were analogs of fluconazole, was designed and synthesized by click chemistry. In the study reported here, the in vitro antifungal activities of all the target compounds were evaluated against eight human pathogenic fungi. Compounds 1a, 1q, and 1r showed the more antifungal activity than the others.

No MeSH data available.


Related in: MedlinePlus