Category: 86386-77-8

Sun, Qing-Yan published the artcileSynthesis of novel triazole derivatives as inhibitors of cytochrome P450 14α-demethylase (CYP51), Computed Properties of 86386-77-8, the publication is European Journal of Medicinal Chemistry (2007), 42(9), 1226-1233, database is CAplus and MEDLINE.

A series of 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-[(4-substitutedphenyl)-piperazin-1-yl]-propan-2-ols have been designed and synthesized on the basis of the structure-activity relationships and antimycotic mechanism of azole antifungal agents. Their structures were confirmed by elemental anal., IR, MS and ¹H NMR. Results of preliminary antifungal tests against eight human pathogenic fungi (Candida albicans, Candida parapsilosis, Candida tropicalis, Cryptococcus neoformans, Aspergillus fumigatus, Trichophyton rubrum, Fonsecaea compacta, and Microsporum gypseum) in vitro showed that all title compounds exhibited activity against fungi tested to some extent. Among the compounds tested, all compounds showed higher activity against C. albicans than fluconazole in vitro. Several compounds exhibited the same activities against C. albicans as voriconazole (with the MIC value of 0.0152 μg/mL). Three compounds showed higher activity against C. parapsilosis than all five pos. controls.

European Journal of Medicinal Chemistry published new progress about 86386-77-8. 86386-77-8 belongs to triazoles, auxiliary class Epoxides,Triazole,Fluoride,Salt,Sulfonic acid,Benzene, name is 1-((2-(2,4-Difluorophenyl)oxiran-2-yl)methyl)-1H-1,2,4-triazole methanesulfonate, and the molecular formula is C24H20Ge, Computed Properties of 86386-77-8.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Liu, Chaomei published the artcileSynthesis and antifungal activities of 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-substituted group-2-propanols, HPLC of Formula: 86386-77-8, the publication is Zhongguo Yaowu Huaxue Zazhi (2004), 14(3), 129-133, database is CAplus.

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.

Zhongguo Yaowu Huaxue Zazhi published new progress about 86386-77-8. 86386-77-8 belongs to triazoles, auxiliary class Epoxides,Triazole,Fluoride,Salt,Sulfonic acid,Benzene, name is 1-((2-(2,4-Difluorophenyl)oxiran-2-yl)methyl)-1H-1,2,4-triazole methanesulfonate, and the molecular formula is C12H13F2N3O4S, HPLC of Formula: 86386-77-8.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Fu, Ben published the artcileSynthesis and bioactivity evaluation of novel azoles containing dithiocarbamate moieties, Category: triazoles, the publication is Medicinal Chemistry Research (2017), 26(10), 2491-2498, database is CAplus.

A series of novel azoles, N-methyl-N-[2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)]-propyl-(1-substituted phenyl)-dithiocarbamate derivatives(i.e. I) has been designed, synthesized and screened for antifungal activity by min. inhibitory concentration Results of preliminary antifungal tests showed that most of the title compounds had good antifungal activities against nearly all the tested fungal pathogens, especially against the Candida species. The most surprising finding of this study is that compound I exhibited higher activities than fluconazole against Aspergillus fumigatus.

Medicinal Chemistry Research published new progress about 86386-77-8. 86386-77-8 belongs to triazoles, auxiliary class Epoxides,Triazole,Fluoride,Salt,Sulfonic acid,Benzene, name is 1-((2-(2,4-Difluorophenyl)oxiran-2-yl)methyl)-1H-1,2,4-triazole methanesulfonate, and the molecular formula is C12H13F2N3O4S, Category: triazoles.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Jiang, Zhigan published the artcileDiscovery of highly potent triazole antifungal derivatives by heterocycle-benzene bioisosteric replacement, Formula: C12H13F2N3O4S, the publication is European Journal of Medicinal Chemistry (2013), 16-22, database is CAplus and MEDLINE.

On the basis of the authors’ previously discovered triazole antifungal lead compounds, heterocycle-benzene bioisosteric replacement was used to improve their pharmacokinetic profile. The designed new triazole derivatives have good antifungal activity toward a wide range of pathogenic fungi. Their binding mode with the target enzyme was clarified by mol. docking. The MIC value of the highly potent compound 1-(4-(benzo[d]thiazol-2-yl-methyl)piperazin-1-yl)-2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol against Candida albicans, Candida tropicalis, and Cryptococcus neoformans is 0.016 μg/mL, 0.004 μg/mL, and 0.016 μg/mL, resp. Moreover, preliminary pharmacokinetic studies revealed that it showed improved oral absorption as compared to the lead compound iodiconazole and deserved for further evaluations.

European Journal of Medicinal Chemistry published new progress about 86386-77-8. 86386-77-8 belongs to triazoles, auxiliary class Epoxides,Triazole,Fluoride,Salt,Sulfonic acid,Benzene, name is 1-((2-(2,4-Difluorophenyl)oxiran-2-yl)methyl)-1H-1,2,4-triazole methanesulfonate, and the molecular formula is C12H13F2N3O4S, Formula: C12H13F2N3O4S.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Gao, Yijun published the artcileDesign and synthesis of fluconazole derivatives, Quality Control of 86386-77-8, the publication is Zhongguo Xinyao Zazhi (2012), 21(6), 681-685, 700, database is CAplus.

Fluconazole derivatives I [wherein R = cyclopropyl, 1-Bu, 1-Pr, allyl, propargyl, iso-Bu, cyclopentyl, iso-Pr, Et, 1-pentyl, 1-hexyl, cyclohexyl, or benzyl] were designed and synthesized. Based on the previous result of computer-aided drug design, we systematically altered the structure of fluconazole according to the structure-activity relationships of the azoles in antifungal compounds and synthesized target compounds in six steps. Thirteen new compounds were synthesized. The structures were confirmed by ¹H-NMR and MS. The design of synthetic route is reasonable. Target compounds are correct and can be used for further study of pharmacol. activities.

Zhongguo Xinyao Zazhi published new progress about 86386-77-8. 86386-77-8 belongs to triazoles, auxiliary class Epoxides,Triazole,Fluoride,Salt,Sulfonic acid,Benzene, name is 1-((2-(2,4-Difluorophenyl)oxiran-2-yl)methyl)-1H-1,2,4-triazole methanesulfonate, and the molecular formula is C12H13F2N3O4S, Quality Control of 86386-77-8.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Yu, Shichong published the artcileMolecular docking, design, synthesis and antifungal activity study of novel triazole derivatives containing the 1,2,3-triazole group, Product Details of C12H13F2N3O4S, the publication is RSC Advances (2013), 3(32), 13486-13490, database is CAplus.

A series of 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-[N-propyl-N-((1-substituted-1H-1,2,3-triazol-4-yl)methyl)amino]-2-propanols which are analogs of fluconazole, have been designed and synthesized on the basis of computational docking experiments to the active site of the cytochrome P 450 14α-demethylase (CYP51). Their structures were characterized by ¹H NMR, ¹³C NMR and HR ESI MS. The MIC₈₀ values indicate that the target compounds, e.g., I, showed higher activities against nearly all the fungi tested to some extent except against A. fum. and T. rub. All of the target compounds exhibited higher activities against C. alb. SC5314 and C. alb. Y0109 than all of the six pos. controls.

RSC Advances published new progress about 86386-77-8. 86386-77-8 belongs to triazoles, auxiliary class Epoxides,Triazole,Fluoride,Salt,Sulfonic acid,Benzene, name is 1-((2-(2,4-Difluorophenyl)oxiran-2-yl)methyl)-1H-1,2,4-triazole methanesulfonate, and the molecular formula is C20H21ClN4O4, Product Details of C12H13F2N3O4S.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Yu, Shichong published the artcileSynthesis and antifungal activity of the novel triazole derivatives containing 1,2,3-triazole fragment, Computed Properties of 86386-77-8, the publication is Archives of Pharmacal Research (2013), 36(10), 1215-1222, database is CAplus and MEDLINE.

A series of fluconazole analogs containing a 1,2,3-triazole fragment has been designed and synthesized on the basis of the active site of the cytochrome P 450 14α-demethylase (CYP51). Their structures were characterized by ¹H NMR, ¹³C NMR, and LC-MS. The MIC₈₀ values indicate that the target compounds showed higher activities against nearly all the fungi tested to some extent except against Aspergillus fumigatus. Several compounds, e.g. I, showed 128 times higher activity (with the MIC₈₀ value of 0.0039 mg/mL) than that of fluconazole against Candida albicans and also showed higher activity than that of the other pos. controls.

Archives of Pharmacal Research published new progress about 86386-77-8. 86386-77-8 belongs to triazoles, auxiliary class Epoxides,Triazole,Fluoride,Salt,Sulfonic acid,Benzene, name is 1-((2-(2,4-Difluorophenyl)oxiran-2-yl)methyl)-1H-1,2,4-triazole methanesulfonate, and the molecular formula is C7H16ClNO2, Computed Properties of 86386-77-8.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Wang, Wenya published the artcileDiscovery of highly potent antifungal triazoles by structure-based lead fusion, Application of 1-((2-(2,4-Difluorophenyl)oxiran-2-yl)methyl)-1H-1,2,4-triazole methanesulfonate, the publication is MedChemComm (2011), 2(11), 1066-1072, database is CAplus.

By means of structure-based lead fusion, a series of novel drug-like azoles possessing 4-(benzyloxy)piperidin-1-yl side chains were rationally designed and synthesized. Flexible mol. docking studies indicated that the newly synthesized azoles took advantages of the key interactions between the two lead structures and CACYP51. As a result, they revealed improved antifungal activity and broader spectrum. All the new azoles showed good to excellent in vitro antifungal activity against all of the tested pathogenic fungi (MIC₈₀ range: 2.33-0.01 μM). Compounds 10a, 10g and 10h, the most active azoles toward Candida albicans (MIC₈₀ = 0.01 μM) are 82 fold more potent than fluconazole. In particular, all the compounds also showed good activity against Aspergillus fumigatus (MIC₈₀ = 2.33-0.55 μM) that is not sensitive to fluconazole.

MedChemComm published new progress about 86386-77-8. 86386-77-8 belongs to triazoles, auxiliary class Epoxides,Triazole,Fluoride,Salt,Sulfonic acid,Benzene, name is 1-((2-(2,4-Difluorophenyl)oxiran-2-yl)methyl)-1H-1,2,4-triazole methanesulfonate, and the molecular formula is C12H15BO4, Application of 1-((2-(2,4-Difluorophenyl)oxiran-2-yl)methyl)-1H-1,2,4-triazole methanesulfonate.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Sheng, Chunquan published the artcileImproved model of lanosterol 14α-demethylase by ligand-supported homology modeling: validation by virtual screening and azole optimization, Application In Synthesis of 86386-77-8, the publication is ChemMedChem (2010), 5(3), 390-397, database is CAplus and MEDLINE.

Lanosterol 14α-demethylase (CYP51) is an important target for antifungal drugs. An improved three-dimensional model of CYP51 from Candida albicans (CACYP51) was constructed by ligand-supported homol. modeling and mol. dynamics simulations. The accuracy of the constructed model was evaluated by its performance in a small-scale virtual screen. The results show that known CYP51 inhibitors were efficiently discriminated by the model, and it performed better than our previous CACYP51 model. The active site of CACYP51 was characterized by multiple copy simultaneous search (MCSS) calculations On the basis of the MCSS results, a series of novel azoles were designed and synthesized, and they showed good in vitro antifungal activity with a broad spectrum. The MIC₈₀ value of four of these compounds against C. albicans is 0.001 μg mL^-1, indicating that they are promising leads for the discovery of novel antifungal agents.

ChemMedChem published new progress about 86386-77-8. 86386-77-8 belongs to triazoles, auxiliary class Epoxides,Triazole,Fluoride,Salt,Sulfonic acid,Benzene, name is 1-((2-(2,4-Difluorophenyl)oxiran-2-yl)methyl)-1H-1,2,4-triazole methanesulfonate, and the molecular formula is C12H16BN3O2, Application In Synthesis of 86386-77-8.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Wang, Wenya published the artcileDiscovery of highly potent antifungal triazoles by structure-based lead fusion, Application of 1-((2-(2,4-Difluorophenyl)oxiran-2-yl)methyl)-1H-1,2,4-triazole methanesulfonate, the publication is MedChemComm (2011), 2(11), 1066-1072, database is CAplus.

By means of structure-based lead fusion, a series of novel drug-like azoles possessing 4-(benzyloxy)piperidin-1-yl side chains were rationally designed and synthesized. Flexible mol. docking studies indicated that the newly synthesized azoles took advantages of the key interactions between the two lead structures and CACYP51. As a result, they revealed improved antifungal activity and broader spectrum. All the new azoles showed good to excellent in vitro antifungal activity against all of the tested pathogenic fungi (MIC₈₀ range: 2.33-0.01 μM). Compounds 10a, 10g and 10h, the most active azoles toward Candida albicans (MIC₈₀ = 0.01 μM) are 82 fold more potent than fluconazole. In particular, all the compounds also showed good activity against Aspergillus fumigatus (MIC₈₀ = 2.33-0.55 μM) that is not sensitive to fluconazole.

MedChemComm published new progress about 86386-77-8. 86386-77-8 belongs to triazoles, auxiliary class Epoxides,Triazole,Fluoride,Salt,Sulfonic acid,Benzene, name is 1-((2-(2,4-Difluorophenyl)oxiran-2-yl)methyl)-1H-1,2,4-triazole methanesulfonate, and the molecular formula is C12H15BO4, Application of 1-((2-(2,4-Difluorophenyl)oxiran-2-yl)methyl)-1H-1,2,4-triazole methanesulfonate.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics