Efficient synthesis and antimicrobial activity of some novel S-β-d-glucosides of 5-aryl-1,2,4-triazole-3-thiones derivatives

Ji, Dan; Lu, Junrui; Lu, Bo-Wei; Chun-Wei, Xin; Mu, Jiangbei; Li, Jianfa; Peng, ChunYong; Xiu-rong, Bao

doi:10.1016/j.bmcl.2013.02.038

Cited by 29 publications

(14 citation statements)

References 16 publications

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“…Encouraged by these observations, we synthesized a series of novel 1,5‐benzodiazepine derivatives based on the principle of superposition . The structures of these newly synthesized 1,5‐benzodiazepine derivatives are shown in Figure .…”

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confidence: 99%

Efficient Synthesis and Biological Evaluation of a Novel Series of 1,5‐Benzodiazepine Derivatives as Potential Antimicrobial Agents

Zhenfang

Zhang

et al. 2016

Chem Biol Drug Des

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A series of novel 1,5-benzodiazepine derivatives were rationally designed and synthesized following the principle of the superposition of bioactive substructures by the combination of 1,5-benzodiazepine, pyridine (phenyl), and an ester group. The structures of the target compounds were determined by (1) H NMR, (13) C NMR, MS, IR, and elemental analysis. All the synthesized compounds were evaluated for their antimicrobial activities in vitro against the fungi C. neoformans, C. neoformans clinical isolates (ATCC 32264), C. albicans (ATCC 10231), Gram-negative bacterium E. coli (ATCC 44752), and Gram-positive bacterium S. aureus (ATCC 25923). The results of the bioactive assay demonstrated that most of the tested compounds exhibited variable inhibitory effects on the growth of the tested microorganisms. All the active compounds showed better antifungal activity than antibacterial activity. Notably, compound 2b displayed the highest activity (MIC = 30 μg/mL) against C. neoformans and (MIC = 31 μg/mL) against C. neoformans clinical isolates. In addition, compound 2a also showed excellent activity against C. neoformans and C. neoformans clinical isolates with minimum inhibitory concentration of 35 and 36 μg/mL, respectively. Compounds 2a and 2b were further studied by evaluating their cytotoxicities, and the results showed that they have relatively low level cytotoxicity for BV2 and 293T cell. Preliminary structure-activity relationship study on three diverse sets (C-2, C-3, and C-8 positions) of 1,5-benzodiazepines was performed. The results revealed that the presence of a -CH3 group at the C-8 position had a positive effect on the inhibitory activity of these compounds. Additionally, the 2-pyridyl group at the C-2 position may be a pharmacophore and -COOC2 H5 at C-3 position is the best substituent for the maintenance of antimicrobial activities.

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confidence: 99%

Efficient Synthesis and Biological Evaluation of a Novel Series of 1,5‐Benzodiazepine Derivatives as Potential Antimicrobial Agents

Zhenfang

Zhang

et al. 2016

Chem Biol Drug Des

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“…The acid hydrazide 6 was allowed to react with carbon disulphide in the presence of potassium hydroxide in methanol to give the corresponding potassium dithiocarbazinate 7. This salt underwent ring closure with an excess of hydrazine hydrate to give 4-amino-5-aryl-4H -1,2,4-triazole-3-thiol (8a-i) [1,21,22]. In the final step, treatment of the oxirane 4 with the appropriate thiol 8 in the presence of NaHCO 3 in absolute ethanol at room temperature gave final compounds 9a-i and 10a-i ( Table 1).…”

Section: Designed Compoundsmentioning

confidence: 99%

“…Since the antibacterial activity of 4-amino-3-mercapto-1,2,4-triazoles has been reported previously [21][22][23], thus the newly synthesized compounds were screened for antibacterial activity. The MIC values of compounds 9a-i and 10a-i were determined against Staphylococcus aureus (ATCC 6538), Staphylococcus epidermidis (ATCC 12228), Bacillus subtilis (ATCC 6633), E. coli (ATCC 8739), Pseudomonas aeruginosa (ATCC 9027) and Klebsiella pneumoniae (ATCC 10031) based on the conventional agar dilution method [24].…”

Section: Biologymentioning

confidence: 99%

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Novel triazole alcohol antifungals derived from fluconazole: design, synthesis, and biological activity

et al. 2014

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A series of new triazole alcohol antifungals were designed by replacing one of the triazolyl moiety from fluconazole with a distinct 4-amino-3-mercapto-1,2,4-triazole motif, which is found in some antimicrobial agents. The antimicrobial susceptibility testing of target compounds demonstrated that the direct analogs of fluconazole (difluorophenethyl-triazoles) were less active against fungi, while compound 10h containing dichloro substitutions on both phenyl rings of the molecule had potent activity against yeasts including Candida albicans (four strains) and Cryptococcus neoformans (MICs = 2-8 μg/mL). Also, compound 10h was active against Candida parapsilosis, Epidermophyton floccosum, and Trichophyton mentagrophytes, while it showed no activity against Gram-positive and Gram-negative bacteria. Finally, a molecular docking study suggested that compound 10h interacts suitably with lanosterol 14α-demethylase, which is the key enzyme in ergosterol biosynthesis.

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“…In line with the present results, Shi et al (23) and Ramírez et al (24) showed that the newly synthesized azole-based compounds were more active than fluconazole and the combination of these compounds with fluconazole could exert synergistic effects. Moreover, Ji et al (25) synthesized triazole derivatives based on the structure of lanosterol 14␣-demethylase (CYP51) and revealed that these compounds have better activity against C. albicans than does fluconazole. ATTAF-1 and ATTAF-2 share general structural features with the triazole alcohol class of antifungal agents, while exhibiting novel and distinct characteristics.…”

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confidence: 99%

In Vitro Activities of Novel Azole Compounds ATTAF-1 and ATTAF-2 against Fluconazole-Susceptible and -Resistant Isolates of Candida Species

Fakhim

Emami

Vaezi

et al. 2017

Antimicrob Agents Chemother

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The in vitro activities of two novel azole compounds (aryl-1,2,4-triazol-3-ylthio analogues of fluconazole [ATTAFs]) and five comparator antifungal agents against 52 clinical Candida isolates from 5 different species were determined. The novel azole compounds had the lowest geometric mean MICs, followed by fluconazole. Moreover, combinations of these compounds with fluconazole exhibited synergistic effects against fluconazole-susceptible (22 of 23 isolates), fluconazole-susceptible dose-dependent (10 of 13 isolates), and fluconazole-resistant (1 of 16 isolates) Candida isolates.

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Efficient synthesis and antimicrobial activity of some novel S-β-d-glucosides of 5-aryl-1,2,4-triazole-3-thiones derivatives

Cited by 29 publications

References 16 publications

Efficient Synthesis and Biological Evaluation of a Novel Series of 1,5‐Benzodiazepine Derivatives as Potential Antimicrobial Agents

Efficient Synthesis and Biological Evaluation of a Novel Series of 1,5‐Benzodiazepine Derivatives as Potential Antimicrobial Agents

Novel triazole alcohol antifungals derived from fluconazole: design, synthesis, and biological activity

In Vitro Activities of Novel Azole Compounds ATTAF-1 and ATTAF-2 against Fluconazole-Susceptible and -Resistant Isolates of Candida Species

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