58905-21-8

Usage

Uses

Used in Pharmaceutical Synthesis:
1-(4-FLUOROPHENYL)-2-(1H-1,2,4-TRIAZOLE-1-YL)ETHANONE is used as a building block for the synthesis of pharmaceuticals due to its chemical functionalities, which can be incorporated into drug molecules to enhance their properties and effectiveness.
Used in Agricultural Chemicals Synthesis:
1-(4-FLUOROPHENYL)-2-(1H-1,2,4-TRIAZOLE-1-YL)ETHANONE is used as a building block for the synthesis of agricultural chemicals, where its chemical structure can contribute to the development of new pesticides or other agrochemicals with improved performance.
Used in Industrial Chemical Reactions:
1-(4-FLUOROPHENYL)-2-(1H-1,2,4-TRIAZOLE-1-YL)ETHANONE is used as an intermediate in various industrial chemical reactions, leveraging its high reactivity to facilitate the production of other valuable compounds.
Used in Laboratory Chemical Reactions:
1-(4-FLUOROPHENYL)-2-(1H-1,2,4-TRIAZOLE-1-YL)ETHANONE is used as an intermediate in laboratory chemical reactions, where its reactivity can be harnessed for the synthesis of novel compounds or for research purposes in the field of organic chemistry.

InChI:InChI=1/C10H8FN3O/c11-9-3-1-8(2-4-9)10(15)5-14-7-12-6-13-14/h1-4,6-7H,5H2

Upstream product

• 128136-94-7 1-(4-Fluoro-phenyl)-2-[1,2,4]triazol-4-yl-ethanone 
• 288-88-0 1,2,4-Triazole 
• 456-04-2 2-Chloro-4'-fluoroacetophenone 
• 403-29-2 2-bromo-4'-fluoroacetophenone 
• 288-36-8 1,2,3-triazole 
• 288-88-0 1,2,4-Triazole 
• 462-06-6 fluorobenzene 
• 403-42-9 1-(4-fluorophenyl)ethanone 

Downstream Products

• 936105-05-4 4-(4-fluoro-phenyl)-5-[1,2,4]triazol-1-yl-thiazol-2-ylamine 
• 114371-24-3 1-(4-fluorophenyl)-N-methyl-2-(1H-1,2,4-triazol-1-yl)ethanimine N-oxide 
• 168009-79-8 1-[2,3-epoxy-2-(4-fluorophenyl)propyl]-1H-1,2,4-triazole 
• 106325-08-0 epoxiconazole 
• 1394137-23-5 2-(4-(3,5-bis(trifluoromethyl)phenyl)thiazol-2-yl)-1-(1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethylidene)hydrazine 
• 1394137-22-4 1-(1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethylidene)-2-(4-(4-nitrophenyl)thiazol-2-yl)hydrazine 
• 1394137-21-3 2-(4-(4-bromophenyl)thiazol-2-yl)-1-(1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethylidene)hydrazine 

Relevant academic research and scientific papers

Synthesis, optimization, antifungal activity, selectivity, and cyp51 binding of new 2-aryl-3-azolyl-1-indolyl-propan-2-ols

A series of 2-aryl-3-azolyl-1-indolyl-propan-2-ols was designed as new analogs of fluconazole (FLC) by replacing one of its two triazole moieties by an indole scaffold. Two different chemical approaches were then developed. The first one, in seven steps, involved the synthesis of the key intermediate 1-(1H-benzotriazol-1-yl)methyl-1H-indole and the final opening of oxiranes by imidazole or 1H-1,2,4-triazole. The second route allowed access to the target compounds in only three steps, this time with the ring opening by indole and analogs. Twenty azole derivatives were tested against Candida albicans and other Candida species. The enantiomers of the best anti-Candida compound, 2-(2,4-dichlorophenyl)-3-(1H-indol-1-yl)-1-(1H-1,2,4-triazol-1-yl)-propan-2-ol (8g), were analyzed by X-ray diffraction to determine their absolute configuration. The (?)-8g enantiomer (Minimum inhibitory concentration (MIC) = IC80 = 0.000256 μg/mL on C. albicans CA98001) was found with the S-absolute configuration. In contrast the (+)-8g enantiomer was found with the R-absolute configuration (MIC = 0.023 μg/mL on C. albicans CA98001). By comparison, the MIC value for FLC was determined as 0.020 μg/mL for the same clinical isolate. Additionally, molecular docking calculations and molecular dynamics simulations were carried out using a crystal structure of Candida albicans lanosterol 14α-demethylase (CaCYP51). The (?)-(S)-8g enantiomer aligned with the positioning of posaconazole within both the heme and access channel binding sites, which was consistent with its biological results. All target compounds have been also studied against human fetal lung fibroblast (MRC-5) cells. Finally, the selectivity of four compounds on a panel of human P450-dependent enzymes (CYP19, CYP17, CYP26A1, CYP11B1, and CYP11B2) was investigated.

Taming Ambident Triazole Anions: Regioselective Ion Pairing Catalyzes Direct N-Alkylation with Atypical Regioselectivity

Controlling the regioselectivity of ambident nucleophiles toward alkylating agents is a fundamental problem in heterocyclic chemistry. Unsubstituted triazoles are particularly challenging, often requiring inefficient stepwise protection-deprotection strategies and prefunctionalization protocols. Herein we report on the alkylation of archetypal ambident 1,2,4-triazole, 1,2,3-triazole, and their anions, analyzed by in situ 1H/19F NMR, kinetic modeling, diffusion-ordered NMR spectroscopy, X-ray crystallography, highly correlated coupled-cluster computations [CCSD(T)-F12, DF-LCCSD(T)-F12, DLPNO-CCSD(T)], and Marcus theory. The resulting mechanistic insights allow design of an organocatalytic methodology for ambident control in the direct N-alkylation of unsubstituted triazole anions. Amidinium and guanidinium receptors are shown to act as strongly coordinating phase-transfer organocatalysts, shuttling triazolate anions into solution. The intimate ion pairs formed in solution retain the reactivity of liberated triazole anions but, by virtue of highly regioselective ion pairing, exhibit alkylation selectivities that are completely inverted (1,2,4-triazole) or substantially enhanced (1,2,3-triazole) compared to the parent anions. The methodology allows direct access to 4-alkyl-1,2,4-triazoles (rr up to 94:6) and 1-alkyl-1,2,3-triazoles (rr up to 99:1) in one step. Regioselective ion pairing acts in effect as a noncovalent in situ protection mechanism, a concept that may have broader application in the control of ambident systems.

Preparation method of epoxiconazole

The invention relates to a preparation method of epoxiconazole. The preparation method comprises the following steps: in the presence of an inert solvent, enabling fluoroacetophenone and a brominationreagent to react at -10 DEG C to 50 DEG C; carrying out

Novel carbazole-triazole conjugates as DNA-targeting membrane active potentiators against clinical isolated fungi

A series of carbazole-triazole conjugates were designed, synthesized and characterized by IR, NMR, and HRMS spectra. Biological assay showed that most of the synthesized compounds exhibited moderate and even strong antifungal activities, especially 3,6-dibromocarbazolyl triazole 5d displayed excellent inhibitory efficacy against most of the tested fungal strains (MIC = 2–32 μg/mL) and effectively fungicidal ability towards C. albicans, C. tropicals and C. parapsilosis ATCC 22019 (MFC = 4–8 μg/mL). Its combination use with fluconazole could enhance the antifungal efficacy, and compound 5d also did not obviously trigger the development of resistance in C. albicans even after 10 passages. Preliminary mechanism study revealed that the active molecule 5d could depolarize fungal membrane potential and intercalate into DNA to possibly block DNA replication, thus possibly exhibiting its powerful antifungal abilities. Conjugate 5d could interact with HSA, which was constructive for the further design, modification and screening of drug molecules. Docking investigation demonstrated a non-covalent binding of 5d with CYP51 through hydrogen bond and hydrophobicity. These results strongly suggested that compound 5d could act as a potential template for the development of promising antifungal drugs.

Novel alkylated azoles as potent antifungals

Fluconazole (FLC) is the drug of choice when it comes to treat fungal infections such as invasive candidiasis in humans. However, the widespread use of FLC has resulted in the development of resistance to this drug in various fungal strains and, simultaneously has occasioned the need for new antifungal agents. Herein, we report the synthesis of 27 new FLC derivatives along with their antifungal activity against a panel of 13 clinically relevant fungal strains. We also explore their toxicity against mammalian cells, their hemolytic activity, as well as their mechanism of action. Overall, many of our FLC derivatives exhibited broad-spectrum antifungal activity and all compounds displayed an MIC value of 0.03?μg/mL against at least one of the fungal strains tested. We also found them to be less hemolytic and less cytotoxic to mammalian cells than the FDA approved antifungal agent amphotericin B. Finally, we demonstrated with our best derivative that the mechanism of action of our compounds is the inhibition of the sterol 14α-demethylase enzyme involved in ergosterol biosynthesis.

Design, synthesis, & biological activity of new triazole & nitro-triazole derivatives as antifungal agents

In this study two series of fluconazole derivatives bearing nitrotriazole (series A) or piperazine ethanol (series B) side chain were designed and synthesized and then docked in the active site of lanosterol 14α-demethylase enzyme (1EA1) using the Autodock 4.2 program (The scripps research institute, La Jolla, CA, USA). The structures of synthesized compound were confirmed by various methods including elemental and spectral (NMR, CHN, and Mass) analyses. Then antifungal activities of the synthesized compound were tested against several natural and clinical strains of fungi using a broth microdilution assay against several standard and clinical fungi. Nitrotriazole derivatives showed excellent and desirable antifungal activity against most of the tested fungi. Among the synthesized compounds, 5a-d and 5g, possessing nitrotriazole moiety, showed maximum antifungal activity, in particular against several fluconazole-resistant fungi.

OXIME DERIVATIVE, METHOD OF PRODUCING THE SAME AND INSECTICIDE COMPRISING THE SAME AS ACTIVE INGREDIENT

PROBLEM TO BE SOLVED: To provide a compound having excellent insecticidal effect and useful as an active ingredient of an insecticide. SOLUTION: This invention provides an oxime derivative represented by general formula (1) (where Ra, X and n represent definitions described in the specifications) and an insecticide that comprises the same as an active ingredient. COPYRIGHT: (C)2015,JPOandINPIT

Design, synthesis and evaluation of clinafloxacin triazole hybrids as a new type of antibacterial and antifungal agents

A series of clinafloxacin triazole hybrids as a new type of antibacterial and antifungal agents were synthesized for the first time and screened for their antimicrobial efficacy against four Gram-positive bacteria, four Gram-negative bacteria and two fungi by two fold serial dilution technique. The bioactive assay indicated that most of the target compounds displayed broad antimicrobial spectrum and good antibacterial and antifungal activities with low MIC values ranging from 0.25 to 2 μg/mL against all the tested strains which exhibited comparable or even better efficiency in comparison with the reference drugs Chloramphenicol, Clinafloxacin and Fluconazole, respectively. Notably, some synthesized clinafloxacin triazoles showed stronger efficacy against methicillin-resistant Staphylococcus aureus than their parent Clinafloxacin.

Hybrids of ravuconazole: Synthesis and biological evaluation

In continuation of our work on antimicrobial agents, a number of hybrid molecules 4a-y containing thiazole and triazole pharmacophores were designed and synthesized. The structure of the compounds was established by IR, NMR, MS and CHN analysis. All the synthesized compounds were tested for qualitative (Zone of inhibition) and quantitative (MIC) antimicrobial activities against four pathogenic bacteria Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa and two pathogenic fungi Candida albicans and Aspergillus niger. Of all the synthesized compounds screened, most of them show potent antimicrobial activity against Gram positive and Gram negative bacteria as well as the fungi species.

Synthesis, structure, and biological activity of novel 1H-1,2,4-triazol-1- yl-thiazole derivatives

2-Amino-4-aryl-5-(1H-1,2,4-triazol-1-yl)thiazole derivatives were synthesized from the reaction of α-bromo substituted acetophenone and thiourea. The structures were confirmed by elemental analysis, 1H NMR and single crystal X-ray diffraction analysis. Biological evaluation showed that some of them possess antifungal and plant growth regulatory activities. Copyright Taylor & Francis Group, LLC.