Design synthesis and biological evaluation of 3-substituted triazole derivatives

Wang, Bao Gang; Yu, Shi Chong; Chai, Xiao Yun; Yan, Yong; Hu, Hanping; Wu, Qiu Ye

doi:10.1016/j.cclet.2010.11.029

Cited by 8 publications

(4 citation statements)

References 9 publications

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“…It is well known that triazoles are widely used in the development of agrochemicals and medicines based on their highly efficient and broad-spectrum biological activities. [8] But the drug resistance in the triazole structures has been significantly increased because of the frequent use of triazole drugs. [9] As a result, triazolium salts that bear similar chemical structures to triazoles have attracted considerable attention in recent years.…”

Section: Introductionmentioning

confidence: 99%

Bioactivities of Triazolium‐Based N‐Heterocyclic Carbene Salts

Song

Zou

Jin

et al. 2023

Chemistry A European J

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1,2,4-Triazolium salts are precursors of N-heterocyclic carbenes (NHCs), which have been extensively used as effective catalysts and ligands for both asymmetric and nonenantioselective reactions. Nevertheless, they are also a kind of quaternary ammonium compounds (QACs) that possess amphipathic properties. The unique chemical and physical properties of 1,2,4-triazolium salts have received significant attention from scientists focusing on the development of novel bioactive molecules as pesticides and medicines. It is timely and meaningful to summarize the bioactivities of 1,2,4triazolium salt derivatives against various bacteria, fungi, cancer cells, and other pathogens in the past 30 years. Meanwhile, the structure-activity relationship (SAR) of 1,2,4triazolium salts was also summarized. Finally, our perspective on the future development and applications of triazolium salts as agrichemicals or human drugs is presented.

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Section: Introductionmentioning

confidence: 99%

Bioactivities of Triazolium‐Based N‐Heterocyclic Carbene Salts

Song

Zou

Jin

et al. 2023

Chemistry A European J

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“…1-10d were synthesized by reacting the 1-10c with carbon disulphide in presence of KOH and conc sulfuric acid and then reacted with 3-bromo-1propyne to give the side chains 1-10e. The compounds 1-10 were carried out under the click-reaction 13,14 condition in the presence of CuSO 4 and sodium ascorbate. All the title compounds (1-10) described above were characterized by ESI and NMR spectroscopic analysis.…”

mentioning

confidence: 99%

Synthesis and Evaluation of Some Substituted Heterocyclic Fluconazole Analogues as Antifungal Agents

Wang¹,

Zhang²,

Jin³

et al. 2014

Asian J. Chem.

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During the past few decades, fungal infections are the commonly prevalent diseases from which a large proportion of the human population suffers 1-5. The increased emergence of both the superficial and systemic fungal infections has led to the massive increase in the rate of mortality, especially in the immuno-compromised individuals, those suffering from tuberculosis, cancer or AIDS 6,7. In clinic, azoles, especially triazole antifungal agents, were used most widely and efficiently. For example, fluconazole, voriconazole and itraconazole, presently play an important role in the treatment of fungal infections. However, their clinical use has been limited by the emergence of drug resistance, high risk of toxicity, insufficiencies in their antifungal activity and undesirable side effects 8-10. Hence, there is still a need to develop the safe and efficient chemotherapeutic agents with potent broad spectrum antifungal activities 10. EXPERIMENTAL Analytical TLC was carried out on Silica Gel 60 F254 plates (E. Merck) with detection by fluorescence and/or by charring with 10 % (v/v) H2SO4 in EtOH. Column chromatograph was performed on silica gel (200-300 mesh, Qindao Ocean Chemical Co., China). All chemicals and solvents were purchased from commercial sources unless specified otherwise. 1 H and 13 C NMR spectra were recorded in CDCl3, using

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“…We intended to alter the side chains to find potent systemic antifungal compounds with a broad antifungal spectrum and less potential to develop resistance. In our previous works [10][11][12][13][14][15][16], many studies on the structure-activity relationships (SAR) of antifungal azoles have been developed, and these studies have led to new compounds endowed with better biological and pharmacological properties.…”

Section: Introductionmentioning

confidence: 99%

“…The increasing frequency of fungal infections and development of resistance to the current treatment highlight the need for development of new triazole derivatives possessing broader antifungal spectra and higher therapeutic indexes. Azole antifungals act by competitive inhibition of CYP51, the enzyme that catalyzes the oxidative removal of the 14α-methyl group of lanosterol to give Δ 14,15 -desaturated intermediates in ergosterol biosynthesis [5]. In general, the active site of CYP51 for ligand binding can be divided into four subsites: a coordination bond with iron of the heme group, the hydrophilic H-bonding region, the hydrophobic region, and the narrow hydrophobic cleft formed by the residues in the helix B'-meander 1 loop and N-terminus of helix I [6].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antifungal Activity of Novel Triazole Compounds Containing Piperazine Moiety

Wang

Bai

et al. 2014

Molecules

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Design and synthesis of triazole library antifungal agents having piperazine side chains, analogues to fluconazole were documented. The synthesis highlighted utilization of the click chemistry on the basis of the active site of the cytochrome P450 14α-demethylase (CYP51). Their structures were characterized by 1 H-NMR, 13 C-NMR, MS and IR. The influences of piperazine moiety on in vitro antifungal activities of all the target compounds were evaluated against eight human pathogenic fungi.

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Design synthesis and biological evaluation of 3-substituted triazole derivatives

Cited by 8 publications

References 9 publications

Bioactivities of Triazolium‐Based N‐Heterocyclic Carbene Salts

Bioactivities of Triazolium‐Based N‐Heterocyclic Carbene Salts

Synthesis and Evaluation of Some Substituted Heterocyclic Fluconazole Analogues as Antifungal Agents

Synthesis and Antifungal Activity of Novel Triazole Compounds Containing Piperazine Moiety

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