Category: 86404-63-9

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 86404-63-9, is researched, SMILESS is FC1=CC=C(C(CN2N=CN=C2)=O)C(F)=C1, Molecular C10H7F2N3OJournal, Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov’t, Journal of Medicinal Chemistry called Alkylated Piperazines and Piperazine-Azole Hybrids as Antifungal Agents, Author is Thamban Chandrika, Nishad; Shrestha, Sanjib K.; Ngo, Huy X.; Tsodikov, Oleg V.; Howard, Kaitlind C.; Garneau-Tsodikova, Sylvie, the main research direction is alkylated piperazine azole hybrid synthesis antifungal.COA of Formula: C10H7F2N3O.

The extensive use of fluconazole (FLC) and other azole drugs has caused the emergence and rise of azole-resistant fungi. The fungistatic nature of FLC in combination with toxicity concerns have resulted in an increased demand for new azole antifungal agents. Herein, we report the synthesis and antifungal activity of novel alkylated piperazines and alkylated piperazine-azole hybrids, their time-kill studies, their hemolytic activity against murine erythrocytes, as well as their cytotoxicity against mammalian cells. Many of these mols. exhibited broad-spectrum activity against all tested fungal strains, with excellent min. inhibitory concentration (MIC) values against non-albicans Candida and Aspergillus strains. The most promising compounds were found to be less hemolytic than the FDA-approved antifungal agent voriconazole (VOR). Finally, we demonstrate that the synthetic alkylated piperazine-azole hybrids do not function by fungal membrane disruption, but instead by disruption of the ergosterol biosynthetic pathway via inhibition of the 14α-demethylase enzyme present in fungal cells.

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Reference:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application In Synthesis of 1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone, is researched, Molecular C10H7F2N3O, CAS is 86404-63-9, about Design and synthesis of new fluconazole analogues.

We have synthesized new fluconazole analogs containing two different 1,2,3-triazole units in the side chain. The synthesis of new amide analogs using a variety of acids is also described. All the compounds showed very good antifungal activity. A hemolysis study of the most active compounds I and II showed that both compounds did not cause any hemolysis at the dilutions tested. These compounds did not exhibit any toxicity to L929 cells at MIC and lower concentrations In the docking study, the overall binding mode of I and II appeared to be reasonable and provided a good insight into the structural basis of inhibition of Candida albicans Cyp51 by these compounds

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Reference:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

COA of Formula: C10H7F2N3O. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone, is researched, Molecular C10H7F2N3O, CAS is 86404-63-9, about Development and validation of a liquid chromatographic method for the stability study of a pharmaceutical formulation containing voriconazole using cellulose tris(4-chloro-3-methylphenylcarbamate) as chiral selector and polar organic mobile phases. Author is Servais, Anne-Catherine; Moldovan, Radu; Farcas, Elena; Crommen, Jacques; Roland, Isabelle; Fillet, Marianne.

The ophthalmic solution of voriconazole, i.e. (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, made from an injection formulation which also contains sulfobutylether-β-cyclodextrin sodium salt as an excipient (Vfend), is used for the treatment of fungal keratitis. A liquid chromatog. (LC) method using polar organic mobile phase and cellulose tris(4-chloro-3-methylphenylcarbamate) coated on silica as chiral stationary phase was successfully developed to evaluate the chiral stability of the ophthalmic solution The percentage of methanol (MeOH) in the mobile phase containing acetonitrile (ACN) as the main solvent significantly influenced the retention and resolution of voriconazole and its enantiomer ((2S,3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol). The optimized mobile phase consisted of ACN/MeOH/diethylamine/trifluoroacetic acid (80/20/0.1/0.1; volume/volume/volume/volume). The method was found to be selective not only regarding the enantiomer of voriconazole but also regarding the specified impurities described in the monograph from the European Pharmacopoeia. The LC method was then fully validated applying the strategy based on total measurement error and accuracy profiles. Under the selected conditions, the determination of 0.1% of voriconazole enantiomer could be performed. Finally, a stability study of the ophthalmic solution was conducted using the validated LC method.

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Reference:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone, is researched, Molecular C10H7F2N3O, CAS is 86404-63-9, about Structure-Based Optimization of Azole Antifungal Agents by CoMFA, CoMSIA, and Molecular Docking. Author is Sheng, Chunquan; Zhang, Wannian; Ji, Haitao; Zhang, Min; Song, Yunlong; Xu, Hui; Zhu, Jie; Miao, Zhenyuan; Jiang, Qingfen; Yao, Jianzhong; Zhou, Youjun; Zhu, Jue; Lue, Jiaguo.

In a continuing effort to develop highly potent azole antifungal agents, the three-dimensional quant. structure-activity relationship methods, CoMFA and CoMSIA, were applied using a set of novel azole antifungal compounds The binding mode of the compounds at the active site of lanosterol 14α-demethylase was further explored using the flexible docking method. Various hydrophobic, van der Waals, π-π stacking, and hydrogen bonding interactions were observed between the azoles and the enzyme. Based on results from the mol. modeling, a receptor-based pharmacophore model was established to guide the rational optimization of the azole antifungal agents. Thus, a total of 57 novel azoles were designed and synthesized by a three-step optimization process. In vitro antifungal assay revealed that the antifungal activities of these novel azoles were greatly improved, which confirmed the reliability of the model from mol. modeling.

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Reference:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Discovery of highly potent novel antifungal azoles by structure-based rational design》. Authors are Wang, Wenya; Sheng, Chunquan; Che, Xiaoying; Ji, Haitao; Cao, Yongbing; Miao, Zhenyuan; Yao, Jianzhong; Zhang, Wannian.The article about the compound:1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanonecas:86404-63-9,SMILESS:FC1=CC=C(C(CN2N=CN=C2)=O)C(F)=C1).Name: 1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone. Through the article, more information about this compound (cas:86404-63-9) is conveyed.

On the basis of the active site of lanosterol 14α-demethylase from Candida albicans (CACYP51), a series of new azoles were designed and synthesized. All the new azoles show excellent in vitro activity against most of the tested pathogenic fungi, which represent a class of promising leads for the development of novel antifungal agents. The MIC80 value of compounds 8c, 8i and 8n against C. albicans is 0.001 μg/mL, indicating that these compounds are more potent than fluconazole, itraconazole and voriconazole. Flexible mol. docking was used to analyze the structure-activity relationships (SARs) of the compounds The designed compounds interact with CACYP51 through hydrophobic, van der Waals and hydrogen-bonding interactions.

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Reference:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone(SMILESS: FC1=CC=C(C(CN2N=CN=C2)=O)C(F)=C1,cas:86404-63-9) is researched.COA of Formula: C8H12O4. The article 《Synthesis and antifungal activity of 1,2,3-triazole containing fluconazole analogues》 in relation to this compound, is published in Bioorganic & Medicinal Chemistry Letters. Let’s take a look at the latest research on this compound (cas:86404-63-9).

Fluconazole based mimics containing 1,2,3-triazole were designed and synthesized as antifungal agents. Their antifungal activities were evaluated in vitro by measuring the minimal inhibitory concentrations (MICs). Three compounds were found to be more potent against Candida fungal pathogens than control drugs fluconazole and amphotericin B. The studies presented here provide structural modification of fluconazole to give 1,2,3-triazole containing mols. Furthermore, these mols. were evaluated in vivo against Candida albicans i.v. challenge in Swiss mice and antiproliferative activities were tested against human hepatocellular carcinoma Hep3B and human epithelial carcinoma A431. It was found that compound I resulted in 97.4% reduction in fungal load in mice and did not show any profound proliferative effect at lower dose (0.001 mg/mL).

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Reference:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Synthesis and antifungal activities of 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-substituted group-2-propanols, published in 2004-06-30, which mentions a compound: 86404-63-9, Name is 1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone, Molecular C10H7F2N3O, Formula: C10H7F2N3O.

The title compounds 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-(4-alkyloxyphenylpiperazin-1-yl)-2-propanols, e.g. I, and 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-substituted sulfur ether-2-propanols, e.g. II, were synthesized through the reaction of an intermediate epoxide and 4-alkyloxyphenylpiperazines or substituted sulfur alcs. The structures were confirmed by the elementary anal., 1H-MR and IR spectra. MIC80 of all the title compounds were determined by the method recommended by the National Committee for Clin. Laboratory Standards (NCCLS) using the RPMI1640 test medium. The results of the preliminary antifungal test show that all the title compounds exhibited potent antifungal activities to a certain extent. The antifungal activity of 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-(4-alkyloxyphenylpiperazin-1-yl)-2-propanols was more potent than that of 1-(1H,1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-substituted sulfur ether-2-propanols in vitro. The antifungal activities of the four compounds in 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-(4-alkyloxyphenylpiperazin-1-yl)-2-propanols are more potent than that of fluconazole or equal to that of ketoconazole in vitro.

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Reference:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone( cas:86404-63-9 ) is researched.Product Details of 86404-63-9.Lebouvier, Nicolas; Giraud, Francis; Corbin, Typhanie; Na, Young Min; Le Baut, Guillaume; Marchand, Pascal; Le Borgne, Marc published the article 《Efficient microwave-assisted synthesis of 1-(1H-indol-1-yl)-2-phenyl-3-(1H-1,2,4-triazol-1-yl)propan-2-ols as antifungal agents》 about this compound( cas:86404-63-9 ) in Tetrahedron Letters. Keywords: indolyl triazolylpropanol preparation; chloroacetophenone triazole substitution microwave irradiation; triazolylacetophenone preparation epoxidation microwave irradiation; microwave irradiation substitution Corey Chaykovsky epoxidation mediator; aryl triazolylmethyl oxirane preparation indole ring opening. Let’s learn more about this compound (cas:86404-63-9).

Conazole antifungals, in the series of triazole alcs., e.g., I, have been synthesized by ring opening of corresponding oxiranes, e.g., II. These oxiranes were prepared in high yields by Corey-Chaykovsky reaction under microwave irradiation

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Reference:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Product Details of 86404-63-9. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone, is researched, Molecular C10H7F2N3O, CAS is 86404-63-9, about ‘Online’ liquid chromatography/nuclear magnetic resonance mass spectrometry – a powerful spectroscopic tool for the analysis of mixtures of pharmaceutical interest.

Liquid chromatog. (LC), simultaneously coupled with both NMR and mass spectrometry (MS) ‘online’ is a powerful structural tool and has a potentially vast range of uses within the pharmaceutical industry. Data from a mixture of fluconazole and related triazoles were obtained from an LC/NMR-MS system developed ‘inhouse’, demonstrating the power of this novel anal. approach.

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1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone, is researched, Molecular C10H7F2N3O, CAS is 86404-63-9, about Novel triazole alcohol antifungals derived from fluconazole: design, synthesis, and biological activity, the main research direction is triazole alc antifungal fluconazole design synthesis biol activity.Recommanded Product: 1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone.

A series of new triazole alc. 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 Ph rings of the mol. 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-pos. and Gram-neg. bacteria. Finally, a mol. docking study suggested that compound 10h interacts suitably with lanosterol 14α-demethylase, which is the key enzyme in ergosterol biosynthesis.

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Reference:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics