Day: April 15, 2022

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 Process Development of Voriconazole: A Novel Broad-Spectrum Triazole Antifungal Agent, published in 2001-02-28, which mentions a compound: 86404-63-9, Name is 1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone, Molecular C10H7F2N3O, Reference of 1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone.

In the synthesis of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (voriconazole), the relative stereochem. is set in the addition of a 4-(1-metalloethyl)-5-fluoropyrimidine derivative to 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-ethanone. The diastereocontrol of this reaction has been examined by variation of pyrimidine substitution pattern and by changes in the metalation and reaction conditions. Excellent diastereoselection (12:1) is obtained using an organozinc derivative of 6-(1-bromoethyl)-4-chloro-5-fluoropyrimidine. After removal of the chlorine from the pyrimidine ring, the absolute stereochem. of voriconazole is established via a diastereomeric salt resolution process using (1R)-10-camphorsulfonic acid. Synthetic routes to the pyrimidine partner have also been evaluated. The initial six-step development route from 5-fluorouracil has been superseded by a four-step synthesis involving fluorination of Me 3-oxopentanoate and cyclization with formamidine acetate.

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

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: 3222-47-7, is researched, SMILESS is O=C(O)C1=CN=C(C)C=C1, Molecular C7H7NO2Journal, Article, Research Support, Non-U.S. Gov’t, Journal of Medicinal Chemistry called Structure-activity relationship studies of tolfenpyrad reveal subnanomolar inhibitors of Haemonchus contortus development, Author is Le, Thuy G.; Kundu, Abhijit; Ghoshal, Atanu; Nguyen, Nghi H.; Preston, Sarah; Jiao, Yaqing; Ruan, Banfeng; Xue, Lian; Huang, Fei; Keiser, Jennifer; Hofmann, Andreas; Chang, Bill C. H.; Garcia-Bustos, Jose; Wells, Timothy N. C.; Palmer, Michael J.; Jabbar, Abdul; Gasser, Robin B.; Baell, Jonathan B., the main research direction is tolfenpyrad Haemonchus contortus nematode parasiticide pharmacokinetics.Reference of 6-Methylnicotinic acid.

Recently, we have discovered that the registered pesticide, tolfenpyrad, unexpectedly and potently inhibits the development of the L4 larval stage of the parasitic nematode Haemonchus contortus with an IC50 value of 0.03 μM while displaying good selectivity, with an IC50 of 37.9 μM for cytotoxicity. As a promising mol. template for medicinal chem. optimization, we undertook anthelmintic structure-activity relationships for this chem. Modifications of the left-hand side (LHS), right-hand side (RHS), and middle section of the scaffold were explored to produce a set of 57 analogs. Analogs I, II, and III were shown to be the most potent compounds of the series, with IC50 values at a subnanomolar level of potency against the chemotherapeutically relevant fourth larval (L4) stage of H. contortus. Selected compounds from the series also showed promising activity against a panel of other different parasitic nematodes, such as hookworms and whipworms.

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

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone, is researched, Molecular C10H7F2N3O, CAS is 86404-63-9, about New triazole derivatives as antifungal agents: Synthesis via click reaction, in vitro evaluation and molecular docking studies.Recommanded Product: 1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone.

A series of 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-substituted-2-propanols, which are analogs of fluconazole, have been designed and synthesized via Cu(I)-catalyzed azide-alkyne cycloaddition on the basis of computational docking experiments to the active site of the cytochrome P 450 14α-demethylase (CYP51). The in vitro antifungal activities of all the target compounds were evaluated against eight human pathogenic fungi. 4-Methylbenzyl-substituted compound I showed the best antifungal activities.

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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.Quality Control of 6-Methylnicotinic acid. The article 《Alkylated Piperazines and Piperazine-Azole Hybrids as Antifungal Agents》 in relation to this compound, is published in Journal of Medicinal Chemistry. Let’s take a look at the latest research on this compound (cas:86404-63-9).

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

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 3222-47-7, is researched, Molecular C7H7NO2, about Versatile {Cp2Ti} Grafted Hetero-Polyoxotungstate Clusters: Synthesis, Crystal Structure, and Photocurrent Properties, the main research direction is titanocene grafted phosphotungstate cluster preparation crystal mol structure photocurrent; crystal mol structure titanocene grafted phosphotungstate cluster.Quality Control of 6-Methylnicotinic acid.

Polyoxotungstate supported titanocene {Cp2Ti}2+ clusters H6{K8(Cp2Ti)2P4W24O88(PO4)2}·14H2O (1), H6[Na2P4W14O58(Cp2Ti)2]·12H2O (2), and H2[K6{Cp2Ti}{PW9O33(WO2)}2{NC5H3(COOK)2}(NC5H3(CH3)COOK)·22H2O] (3) have been synthesized, and their single crystal x-ray structures have revealed unprecedented and intriguing structural features. The synthesized compounds have been characterized by various spectroscopic techniques including UV-vis, cyclic voltammogram, NMR, ESI-MS, and inductive coupled plasma spectroscopy (ICP) in solution and also by IR, TGA, and diffuse reflectance in the solid state. Clusters 1 and 2 are rare examples of lacunary POM supported titanocene clusters obtained by incorporating various phosphorus heteroatoms to form elusive phosphotungstate assemblies, whereas 3 is an unprecedented organometallic as well as heteroleptic pyridyl functionalized POM. Clusters 1-3 show transient photocurrent ON/OFF behavior upon UV-light irradiation and also exhibit characteristic TiIV/III intravalence electron transfer. This behavior is also established by their cyclic voltammograms in mixed phosphate buffers (Na2HPO4/NaH2PO4) which show the evidence of POM supported {Cp2Ti}2+/+ species in their redox solution Furthermore, ESR line broadening is also observed in these clusters at room temperature, a fact which also confirms the formation of partially reduced/oxidized {Cp2Ti}2+/+ species leading to TiIV/III intravalence electron transfers within all three clusters. The {Cp2Ti}2+ decorated polyoxometalate cluster 3 shows improved transient photocurrent behavior which may be due to the presence of pyridyl carboxyl ions which provide better surface contact for the cluster mol. through the carboxylate moiety to the ITO electrode.

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Reference:
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 Conversion of 4-amino-4H-1,2,4-triazole to 1,3-bis(1H-azol-1-yl)-2-aryl-2-propanols and 1-phenacyl-4-[(benzoyl or 4-toluenesulfonyl)imino]-(1H-1,2,4-triazolium) ylides, the main research direction is propanol azolylaryl preparation; fluconazole analog preparation.Name: 1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone.

1,3-Bis(1H-azol-1-yl)-2-aryl-2-propanols I (A,B = N, CH; Z = halo) were prepared in a one-pot procedure by reacting 1-aryl-2-(1H-1,2,4-triazol-1-yl)- or 1-aryl-2-(1H-imidazol-1-yl)ethanones with dimethylsulfoxonium methide in the presence of either 1,2,4-triazole or imidazole. The aromatic groups in I were either 4-bromo-, 4-chloro-, 2,4-dichloro- or 2,4-difluorophenyl. 4-Amino-4H-1,2,4-triazole was acylated with either benzoyl or 4-toluenesulfonyl chloride to afford [4-(benzoyl or 4-toluenesulfonyl)amino]-4H-1,2,4-triazole. Subsequent alkylations with 4-bromo- or 4-chlorophenacyl bromide produced 1-(4-bromo- or 4-chlorophenacyl)-4-[(benzoyl- or 4-toluenesulfonyl)amino]-1H-1,2,4-triazolium bromides. Neutralizations of these salts provided the corresponding ylides.

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

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Research Support, Non-U.S. Gov’t, Journal of the American Chemical Society called Catalytic Deoxygenative Coupling of Aromatic Esters with Organophosphorus Compounds, Author is Kurosawa, Miki B.; Isshiki, Ryota; Muto, Kei; Yamaguchi, Junichiro, which mentions a compound: 3222-47-7, SMILESS is O=C(O)C1=CN=C(C)C=C1, Molecular C7H7NO2, SDS of cas: 3222-47-7.

We have developed a deoxygenative coupling of aromatic esters with diarylphosphine oxides/dialkyl phosphonates under palladium catalysis. In this reaction, aromatic esters can work as novel benzylation reagents to give the corresponding benzylic phosphorus compounds The key of this reaction is the use of Ph esters, an electron-rich diphosphine as a ligand, and sodium formate as a hydrogen source. Arylcarboxylic acids were also applicable in this reaction using (Boc)2O as an additive. Palladium/dcype worked to activate the acyl C-O bond of the ester and to support the reduction with sodium formate.

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

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.Yu, Shichong; Chai, Xiaoyun; Hu, Honggang; Yan, Yongzheng; Guan, Zhongjun; Zou, Yan; Sun, Qingyan; Wu, Qiuye researched the compound: 1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone( cas:86404-63-9 ).Related Products of 86404-63-9.They published the article 《Synthesis and antifungal evaluation of novel triazole derivatives as inhibitors of cytochrome P450 14α-demethylase》 about this compound( cas:86404-63-9 ) in European Journal of Medicinal Chemistry. Keywords: triazole preparation inhibitor cytochrome P 450 14 alpha demethylase; click reaction triazole preparation antifungal evaluation. We’ll tell you more about this compound (cas:86404-63-9).

A series of 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-substituted-2-propanols, which are analogs of fluconazole, have been designed and synthesized as the potential antifungal agents by the click reaction. Click reaction approach toward the synthesis of two sets of novel 1,2,3-triazolyl linked triazole antifungal derivatives was achieved by Cu(I)-catalyzed 1,3-dipolar cycloaddition of propargylated intermediates with substituted benzyl or alkyl azides. The 1,2,3-triazolyl group was inserted into the side chain of the target mol. which can increase the antifungal activity of compounds

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

Srinivasulu, Vunnam; Al-Marzooq, Farah; Hamad, Mohamad; Khanfar, Monther A.; Ramanathan, Mani; Soares, Nelson C.; Al-Tel, Taleb H. published the article 《Sequencing Groebke-Blackburn-Bienayme and Aza-Michael Addition Reactions: A Modular Strategy for Accessing a Diverse Collection of Constrained Benzoxazepine and Imidazopyrazine Systems》. Keywords: benzoxazepinium fuse imidazopyridine preparation; thiazoimidazobenzooxazepinium trifluoromethane sulfonate preparation; pyridothiazoimidazooxzazepinoquinolium trifluoromethane sulfonate preparation; imidazopyrazinoimidazothiazole preparation.They researched the compound: 4-(4-Bromophenyl)-5-methylthiazol-2-amine( cas:65705-44-4 ).HPLC of Formula: 65705-44-4. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:65705-44-4) here.

A divergent strategy that permitted the access to diversely functionalized benzoxazepinium scaffolds fused to various heterocycles was reported. The described strategy featured a one-pot combination of the Groebke-Blackburn-Bienaym reaction and an aza-Michael addition Me (E)-4-(2-formylphenoxy)but-2-enoates were utilized as central elements in this cascade. These building blocks were reacted with a variety of functionalized amino-azines and tert-Bu isocyanide under ytterbium triflate [Yb(OTf)3] catalysis. The cascade represented a rapid, modular and atom-economic process that leaded to the construction of a diverse collection of constrained benzoxazepinium systems from a wide substrate scope.

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

Lei, Jie; He, Liu-Jun; Tang, Dian-Yong; Wen, Jingyuan; Yan, Wei; Li, Hong-yu; Chen, Zhong-Zhu; Xu, Zhi-Gang published an article about the compound: 6-Methylnicotinic acid( cas:3222-47-7,SMILESS:O=C(O)C1=CN=C(C)C=C1 ).Application In Synthesis of 6-Methylnicotinic acid. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:3222-47-7) through the article.

Chemoselective approaches were developed for derivatizing diastereoselective chromanone spiro-γ-lactams through the Michael-type addition by using amide as a weak nucleophile to construct the spiro-carbon center under basic conditions. To expand the scope of this post-Ugi cascade reaction, a new series of oxidized chromone derivatives Iand II [R1 = H, Me, Cl, etc.; R2 = Ph, 2-thienyl, 1,3-benzodioxol-5-yl, etc.; R3 = 2,6-dimethylphenyl, 4-methoxyphenyl, 1-naphthyl, etc.] was synthesized by altering solvent from EtOH to DMF. Compounds II [R1 = H; R2 = 1,3-benzodioxol-5-yl, 4-nitrophenyl; R3 = 2,6-dimethylphenyl] which could be synthesized in one day, demonstrated comparable anticancer activities with legendary anticancer drug paclitaxel in the PANC and U87 cell lines. This methodol. offers a new approach to construct spiro-carbon centers with functionalized chromanones or chromones under mild reaction conditions.

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