Category: Triazoles

Ostrovskii, V. A. published the artcileStudy of five-membered nitrogen-containing heterocycles by quantum-chemical methods. II. Structure and aromaticity of azoles, Recommanded Product: 4H-1,2,4-Triazole, the publication is Zhurnal Organicheskoi Khimii (1995), 31(9), 1422-1431, database is CAplus.

The MNDO method was used to study the electronic and geometric structure of 5-membered heterocycles, their anions, and their protonated forms. Reactivities, acidities, and basicities were related to at. charges. In contrast to the anions, the neutral and protonated forms exhibit relatively low aromaticity.

Zhurnal Organicheskoi Khimii published new progress about 63598-71-0. 63598-71-0 belongs to triazoles, auxiliary class Triazole, name is 4H-1,2,4-Triazole, and the molecular formula is C2H3N3, Recommanded Product: 4H-1,2,4-Triazole.

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

Jones, Carrie K. published the artcileThe metabotropic glutamate receptor 4-positive allosteric modulator VU0364770 produces efficacy alone and in combination with L-DOPA or an adenosine 2A antagonist in preclinical rodent models of Parkinson’s disease, Product Details of C25H29N9O3, the publication is Journal of Pharmacology and Experimental Therapeutics (2012), 340(2), 404-421, database is CAplus and MEDLINE.

Parkinson’s disease (PD) is a debilitating neurodegenerative disorder associated with severe motor impairments caused by the loss of dopaminergic innervation of the striatum. Previous studies have demonstrated that pos. allosteric modulators (PAMs) of metabotropic glutamate receptor 4 (mGlu₄), including N-phenyl-7-(hydroxyimino)cyclopropa[b]chromen-1a-carboxamide, can produce antiparkinsonian-like effects in preclin. models of PD. However, these early mGlu₄ PAMs exhibited unsuitable physiochem. properties for systemic dosing, requiring intracerebroventricular administration and limiting their broader utility as in vivo tools to further understand the role of mGlu₄ in the modulation of basal ganglia function relevant to PD. In the present study, we describe the pharmacol. characterization of a systemically active mGlu₄ PAM, N-(3-chlorophenyl)picolinamide (VU0364770), in several rodent PD models. VU0364770 showed efficacy alone or when administered in combination with L-DOPA or an adenosine 2A (A_2A) receptor antagonist currently in clin. development (preladenant). When administered alone, VU0364770 exhibited efficacy in reversing haloperidol-induced catalepsy, forelimb asymmetry-induced by unilateral 6-hydroxydopamine (6-OHDA) lesions of the median forebrain bundle, and attentional deficits induced by bilateral 6-OHDA nigrostriatal lesions in rats. In addition, VU0364770 enhanced the efficacy of preladenant to reverse haloperidol-induced catalepsy when given in combination. The effects of VU0364770 to reverse forelimb asymmetry were also potentiated when the compound was coadministered with an inactive dose of L-DOPA, suggesting that mGlu₄ PAMs may provide L-DOPA-sparing activity. The present findings provide exciting support for the potential role of selective mGlu₄ PAMs as a novel approach for the symptomatic treatment of PD and a possible augmentation strategy with either L-DOPA or A_2A antagonists.

Journal of Pharmacology and Experimental Therapeutics published new progress about 377727-87-2. 377727-87-2 belongs to triazoles, auxiliary class GPCR/G Protein,Adenosine Receptor, name is 2-(Furan-2-yl)-7-(2-(4-(4-(2-methoxyethoxy)phenyl)piperazin-1-yl)ethyl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine, and the molecular formula is C25H29N9O3, Product Details of C25H29N9O3.

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

Fray, M. Jonathan published the artcileStructure-Activity Relationships of 1,4-Dihydro-(1H,4H)-quinoxaline-2,3-diones as N-Methyl-D-aspartate (Glycine Site) Receptor Antagonists. 1. Heterocyclic Substituted 5-Alkyl Derivatives, Name: 4H-1,2,4-Triazole, the publication is Journal of Medicinal Chemistry (2001), 44(12), 1951-1962, database is CAplus and MEDLINE.

A series of 6,7-dichloro-1,4-dihydro-(1H,4H)-quinoxaline-2,3-diones were prepared in which the 5-position substituent was a heterocyclylmethyl or 1-(heterocyclyl)-1-Pr group. Structure-activity relationships were evaluated where binding affinity for the glycine site of the N-methyl-D-aspartate (NMDA) receptor was measured using the specific radioligand [³H]-L-689,560, and functional antagonism was demonstrated by inhibition of NMDA-induced depolarizations of rat cortical wedges. The ability to prevent NMDA-induced hyperlocomotion in mice in vivo was measured for selected compounds Binding affinity increased significantly if the heterocyclic group, e.g. 1,2,3-triazol-1-yl could participate in accepting a hydrogen bond from the receptor. It was difficult to obtain compounds with adequate aqueous solubility and strategies to improve it were investigated. The most potent compound in this series, 6,7-dichloro-5-[1-(1,2,4-triazol-4-yl)propyl]-1,4-dihydro-(1H,4H)-quinoxaline-2,3-dione (I) (binding IC₅₀ = 2.6 nM; cortical wedge EC₅₀ = 90 nM), inhibited NMDA-induced hyperlocomotion in mice (6/9 protected at 20 mg/kg iv). Pharmacokinetic parameters, including extent of brain penetration, for I and 6,7-dichloro-5-[(1-propyl-4-imidazolyl)methyl]-1,4-dihydro-(1H,4H)-quinoxaline-2,3-dione are reported.

Journal of Medicinal Chemistry published new progress about 63598-71-0. 63598-71-0 belongs to triazoles, auxiliary class Triazole, name is 4H-1,2,4-Triazole, and the molecular formula is C2H3N3, Name: 4H-1,2,4-Triazole.

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

Zhou, Ru-Shuang published the artcileC-H Amination of Nitro Azaheterocyclic Compounds by Vicarious Nucleophilic Substitution, Recommanded Product: 4-Nitro-2H-1,2,3-triazole, the publication is Synlett (2022), 33(1), 88-92, database is CAplus.

Various nitro azaheterocyclic compounds were subjected to C-H amination by vicarious nucleophilic substitution with 4H-1,2,4-triazol-4-amine (ATA). The aminated products were characterized by NMR, mass spectroscopy, and single-crystal X-ray diffraction analyses. The substrates examined gave moderate to excellent yields (30-88%) and showed good regioselectivities. This protocol offers the advantages of mild conditions, a short reaction time (2-4 h), and an inexpensive, com. available, and less-toxic amination reagent; moreover, no addnl. catalyst or reagent is needed. A possible reaction mechanism is discussed.

Synlett published new progress about 84406-63-3. 84406-63-3 belongs to triazoles, auxiliary class Triazole,Nitro Compound, name is 4-Nitro-2H-1,2,3-triazole, and the molecular formula is C15H14O, Recommanded Product: 4-Nitro-2H-1,2,3-triazole.

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

Hauser, Robert A. published the artcilePreladenant in patients with Parkinson’s disease and motor fluctuations: a phase 2, double-blind, randomised trial, Application In Synthesis of 377727-87-2, the publication is Lancet Neurology (2011), 10(3), 221-229, database is CAplus and MEDLINE.

Preladenant is an adenosine 2A (A_2A) receptor antagonist. In animal models of Parkinson’s disease, preladenant monotherapy improves motor function without causing dyskinesia and, as an adjunct to levodopa, it improves motor function without worsening dyskinesia. We aimed to assess the efficacy and safety of preladenant in patients with Parkinson’s disease and motor fluctuations who were receiving levodopa and other antiparkinsonian drugs. In this phase 2, dose-finding trial, patients with Parkinson’s disease who were receiving levodopa were enrolled and treated at 44 sites in 15 countries between Dec., 2006, and Nov., 2008. Assignment to treatment was done centrally with an interactive voice response system, according to a block randomisation schedule that was computer generated by the sponsor. Patients were assigned to receive 1, 2, 5, or 10 mg oral preladenant twice daily, or matching placebo for 12 wk. Patients, study staff, investigators, and all sponsor personnel were masked to treatment assignment. The primary outcome was change in mean daily off time from baseline to week 12, as assessed by home diaries. Efficacy anal. included all patients who received at least one dose of study drug and had data for assessments after baseline. This trial is registered with ClinicalTrials.gov, number NCT00406029. 253 Patients were randomised to receive preladenant (1 mg [n = 49], 2 mg [n = 49], 5 mg [n = 49], 10 mg [n = 57]) or placebo (n = 49), of whom 234 on preladenant (1 mg [n = 47], 2 mg [n = 48], 5 mg [n = 45], 10 mg [n = 49]) and placebo (n = 45) were eligible for the efficacy anal. Mean daily off time from baseline to week 12 was reduced vs. placebo in patients on 5 mg preladenant (difference -1.0 h, 95% CI -2.1 to 0.0; p = 0.0486) and 10 mg preladenant (-1.2 h, -2.2 to -0.2; p = 0.019). Changes in mean daily off time vs. placebo were not significant for 1 mg preladenant (0.2 h, -0.9 to 1.2; p = 0.753) or 2 mg preladenant (-0.7 h, -1.7 to 0.3; p = 0.162). The most common adverse events in the combined preladenant group vs. placebo were worsening of Parkinson’s disease (22 [11%] vs 4 [9%]), somnolence (20 [10%] vs 3 [6%]), dyskinesia (18 [9%] vs 6 [13%]), nausea (17 [9%] vs 5 [11%]), constipation (15 [8%] vs 1 [2%]), and insomnia (15 [8%] vs 4 [9%]). 5 and 10 mg preladenant twice daily might be clin. useful to reduce off time in patients with Parkinson’s disease and motor fluctuations. Funding: Schering-Plough, a subsidiary of Merck.

Lancet Neurology published new progress about 377727-87-2. 377727-87-2 belongs to triazoles, auxiliary class GPCR/G Protein,Adenosine Receptor, name is 2-(Furan-2-yl)-7-(2-(4-(4-(2-methoxyethoxy)phenyl)piperazin-1-yl)ethyl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine, and the molecular formula is C25H29N9O3, Application In Synthesis of 377727-87-2.

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

Chen, Jing-Lin published the artcileSynthesis, Characterization, and Photophysical Properties of Heteroleptic Copper(I) Complexes with Functionalized 3-(2′-Pyridyl)-1,2,4-triazole Chelating Ligands, Computed Properties of 219508-27-7, the publication is Inorganic Chemistry (2013), 52(17), 9727-9740, database is CAplus and MEDLINE.

Mononuclear Cu(I) complexes (1–9) with functionalized 3-(2′-pyridyl)-1,2,4-triazole chelating ligands, as well as the halide and/or phosphine ancillary ligands, were synthesized. Complexes 1–9 were fully characterized by elemental anal., NMR spectroscopy, mass spectroscopy, electronic absorption spectroscopy, fluorescence spectroscopy, cyclic voltammetry, and x-ray crystallog. (1–8). They adopt a distorted tetrahedral configuration, and are considerably air-stable in solid state and in solution All these Cu(I) complexes display a comparatively weak low-energy absorption in CH₂Cl₂ solution, assigned to charge-transfer transitions with appreciable MLCT character, as supported by TD-DFT studies. Cu(I) halide complexes 1–4 each shows bright solid-state emission at room temperature, though they are nonemissive in fluid solutions, in which emission markedly depends on the halide and the substituent on the 2-pyridyl ring. Complexes 5–9 bearing 2-pyridyl functionalized 1,2,4-triazole and phosphine exhibit good photoluminescence properties in solution and solid states at ambient temperature, which are well-modulated via the alteration of the auxiliary phosphine ligand and the structural modification of 3-(2′-pyridyl)-1,2,4-triazole. Cationic complex 6 and neutral derivative 7 can readily be interconverted through the ring inversion of the 1,2,4-triazolyl regulated by the NH ↔ N^– transformation.

Inorganic Chemistry published new progress about 219508-27-7. 219508-27-7 belongs to triazoles, auxiliary class Trifluoromethylated Building Blocks, name is 2-[5-(Trifluoromethyl)-1H-1,2,4-triazol-3-yl]pyridine, and the molecular formula is C8H5F3N4, Computed Properties of 219508-27-7.

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

Franco, Mauricio P. published the artcileEvaluation of N-binding through N1, N2 or N3 of 4-R-1,2,3-Triazolate to [CuCO]⁺ Complexes, Product Details of C2H2N4O2, the publication is ChemistrySelect (2022), 7(10), e202104006, database is CAplus.

We computationally investigated eight 4-R-1,2,3-triazolates and their three possible N-binding modes. Optimization of the pre-ligands to verify NPA charges were done with M06-2X/def2-TZVPP. The complexes with [CuCO]⁺ were optimized with M06 L/def2-TZVPP and the electronic energies were improved with DLPNO-CCSD(T)/cc-pVTZ. Our calculations with pre-ligands indicated the NPA charge of N2 as less neg. than N1 and N3 by at least ∼0.100 e. Taking into account the complexes energies and vibrations, coordination via N2 is the most stable among all three nitrogens in gas-phase by at least, 8 kJ/mol and the vibrational anal. of the ν_CO indicates linkage isomer N2 as the best electron d. donor among the three linkage isomers. The results exhibit a fine-tuning of ligand donation properties that can be achieved by selecting different R groups in 4-R-1,2,3-triazoles.

ChemistrySelect published new progress about 14544-45-7. 14544-45-7 belongs to triazoles, auxiliary class Triazoles, name is 5-Nitro-1H-1,2,3-triazole, and the molecular formula is C2H2N4O2, Product Details of C2H2N4O2.

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

Gan, Zhi-yong published the artcileSynthesis and characterization of hexaalkylguanidinium TADC energetic ionic liquids, HPLC of Formula: 53817-16-6, the publication is Huozhayao Xuebao (2012), 35(1), 19-22, 31, database is CAplus.

Four kinds of hexaalkylguanidinium 4, 5-dicyano-1, 2, 3-triazole ([C_n-guan][TADC], n=3, 4, 5, 6) energetic ionic liquids were synthesized by an ion exchange technique. Their structures were identified by IR and ¹HNMR. Their d., solubility, thermal properties were studied. Their structures were identified by IR, ¹HNMR, solubility were tested in common organic solvents, d. were measured by surface interfacial tension meter, thermal properties were studied through TG, DSC method. The results showed that hexaalkylguanidinium TADC ionic liquids had good solubility in most of organic solvents. The maximum decomposition temperature was about 370°C, revealing that [C_3-6-guan][TADC] had good thermal stability. In the second heating process of DSC, ([C_n-guan][TADC], n=3, 4, 5) experienced four kinds of phases, glassy, supercooled state, crystalline solid and liquid

Huozhayao Xuebao published new progress about 53817-16-6. 53817-16-6 belongs to triazoles, auxiliary class Triazoles, name is 1H-1,2,3-Triazole-4,5-dicarbonitrile, and the molecular formula is C4HN5, HPLC of Formula: 53817-16-6.

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

Guan, Zhongjun published the artcileSynthesis, molecular docking, and biological evaluation of novel triazole derivatives as antifungal agents, Quality Control of 86386-77-8, the publication is Chemical Biology & Drug Design (2010), 76(6), 496-504, database is CAplus and MEDLINE.

Twenty-eight novel triazoles I (R = 2-FC₆H₄, 4-BrC₆H₄, 3-BrC₆H₄, etc.) and II [4-(MeOSO₂)C₆H₄, 4-(EtOSO₂)C₆H₄, 4-(i-PrOSO₂)C₆H₄, etc.] have been synthesized for structure-activity relationship studies as antifungal agents. The compounds were designed based on the structure of fluconazole and mol. modeling of the active site of the cytochrome P 450 14α-demethylase (CYP51). All of them are reported for the first time. Their chem. structures are characterized by ¹H NMR, ¹³C NMR, LC-MS, and elemental anal. The antifungal activities have been evaluated in vitro by measuring the minimal inhibitory concentrations Compounds I exhibited higher activity against nearly all fungi tested except Aspergillus fumigatus than fluconazole. The computational mol. docking experiments indicated that the inhibition of CYP51 involves a coordination bond with iron of the heme group, a hydrophilic H-bonding region, a hydrophobic region, and a narrow hydrophobic binding cleft.

Chemical Biology & Drug Design 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 artcileSynthesis and antifungal evaluation of novel triazole derivatives as inhibitors of cytochrome P450 14α-demethylase, Name: 1-((2-(2,4-Difluorophenyl)oxiran-2-yl)methyl)-1H-1,2,4-triazole methanesulfonate, the publication is European Journal of Medicinal Chemistry (2010), 45(10), 4435-4445, database is CAplus and MEDLINE.

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

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 C3H6O2, Name: 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