Triazoles

Claff, Tobias published the artcileSingle Stabilizing Point Mutation Enables High-Resolution Co-Crystal Structures of the Adenosine A_2A Receptor with Preladenant Conjugates, Computed Properties of 377727-87-2, the publication is Angewandte Chemie, International Edition (2022), 61(22), e202115545, database is CAplus and MEDLINE.

The G protein-coupled adenosine A_2A receptor (A_2AAR) is an important new (potential) drug target in immuno-oncol., and for neurodegenerative diseases. Preladenant and its derivatives belong to the most potent A_2AAR antagonists displaying exceptional selectivity. While crystal structures of the human A_2AAR have been solved, mostly using the A_2A-StaR2 protein that bears 9 point mutations, co-crystallization with Preladenant derivatives has so far been elusive. We developed a new A_2AAR construct harboring a single point mutation (S91^3.39K) which renders it extremely thermostable. This allowed the co-crystallization of two novel Preladenant derivatives, the polyethylene glycol-conjugated (PEGylated) PSB-2113, and the fluorophore-labeled PSB-2115. The obtained crystal structures (2.25 S and 2.6 S resolution) provide explanations for the high potency and selectivity of Preladenant derivatives They represent the first crystal structures of a GPCR in complex with PEG- and fluorophore-conjugated ligands. The applied strategy is predicted to be applicable to further class A GPCRs.

Angewandte Chemie, International Edition 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, Computed Properties of 377727-87-2.

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

Verkhozina, O. N. published the artcileSynthesis of Polynuclear Nonfused Azoles, Safety of 5-Nitro-1H-1,2,3-triazole, the publication is Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii) (2003), 39(12), 1792-1796, database is CAplus.

Polynuclear blocks consisting of nonfused heterocycles of the azole series, connected through methylene bridges, were synthesized by successive addition of azole units via cycloaddition of organic azides to the triple bond of N-(2-propynyl)azoles, as well as via reaction of azide ion at the cyano group of cyanomethylazoles. Initial N-(2-propynyl)azoles were prepared by reaction of 2-propynyl bromide with 1,2,3-triazoles, benzotriazole, and tetrazoles; cyanomethylazoles were obtained by alkylation of azoles with chloroacetonitrile. An analogous scheme was used to add heterocyclic units to 2-phenyl-1,2,3-triazole-4-carbonitrile. In this case, the 1st two heterocyclic units are linked through the ring C atom. For example, 5-phenyl-2-(tetrazol-5-ylmethyl)tetrazole was prepared from NaN₃ and (5-phenyl-2-tetrazolyl)acetonitrile, the latter of which was prepared from 5-phenyl-2H-tetrazole and chloroacetonitrile.

Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii) 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 C24H29N5O3, Safety of 5-Nitro-1H-1,2,3-triazole.

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

Gareev, G. A. published the artcileReaction of some derivatives of 2-nitro-2-azapropanol with azoles, Category: triazoles, the publication is Zhurnal Organicheskoi Khimii (1988), 24(10), 2221-6, database is CAplus.

Treatment of triazoles and tetrazoles with nitroazapropanol derivatives MeN(NO₂)CH₂X [X = OAc (I), O₂CCF₃, or Cl] afforded N-substituted 2-nitro-2-azapropylazoles. Thus, reaction of 4-substituted tetrazole with I in THF or HCCl₃ (or neat) in the presence H₂SO₄ afforded alkylation products II (R = H, Ph, Me, CH₂:CH, CH₂:CMe, CF₃).

Zhurnal Organicheskoi Khimii 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 C2H2N4O2, Category: triazoles.

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

Comeo, Eleonora published the artcileSubtype-Selective Fluorescent Ligands as Pharmacological Research Tools for the Human Adenosine A_2A Receptor, Computed Properties of 377727-87-2, the publication is Journal of Medicinal Chemistry (2020), 63(5), 2656-2672, database is CAplus and MEDLINE.

Among class A G protein-coupled receptors (GPCR), the human adenosine A_2A receptor (hA_2AAR) remains an attractive drug target. However, translation of A_2AAR ligands into the clinic has proved challenging and an improved understanding of A_2AAR pharmacol. could promote development of more efficacious therapies. Subtype-selective fluorescent probes would allow detailed real-time pharmacol. investigations both in vitro and in vivo. In the present study, two families of fluorescent probes were designed around the known hA_2AAR selective antagonist preladenant (SCH 420814). Both families of fluorescent antagonists retained affinity at the hA_2AAR, selectivity over all other adenosine receptor subtypes and allowed clear visualization of specific receptor localization through confocal imaging. Furthermore, the Alexa Fluor 647-labeled conjugate allowed measurement of ligand binding affinities of unlabeled hA_2AAR antagonists using a bioluminescence resonance energy transfer (NanoBRET) assay. The fluorescent ligands developed here can therefore be applied to a range of fluorescence-based techniques to further interrogate hA_2AAR pharmacol. and signaling.

Journal of Medicinal Chemistry 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, Computed Properties of 377727-87-2.

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

Szaboo, Nikoletta published the artcileNovel therapy in Parkinson’s disease: adenosine A_2A receptor antagonists, HPLC of Formula: 377727-87-2, the publication is Expert Opinion on Drug Metabolism & Toxicology (2011), 7(4), 441-455, database is CAplus and MEDLINE.

A review. Introduction: Parkinson’s disease (PD) is a progressive neurodegenerative disorder. To date, most of the currently available therapies in PD target the dopaminergic system and none of these therapeutic approaches have been proven to modify the course of the disease. To various extents, these drugs can also cause motor and non-motor complications. A novel target, the adenosine A_2A receptor (AA2AR), was recently identified, blockade of which may alleviate Parkinsonian symptoms, reduce motor fluctuations and potentially afford neuroprotection. Areas covered: This review is based on a PubMed search covering the relationship of the adenosine receptors and PD. The role of the AA2AR is reviewed and the results of preclin. investigations of antagonists are assessed. A synopsis of current drug development is provided, with a special focus on the pharmacokinetics and relevant clin. trials. Expert opinion: The localization of the AA2AR in the central nervous system, the ultra structural localization and the mol. mechanism of its action reveal the potential importance of the AA2AR in movement disorders. The theor. background and exptl. data indicate that AA2AR antagonists may have a potential therapeutic effect in Parkinson’s disease. More importantly, the putative neuroprotective effect needs further investigation.

Expert Opinion on Drug Metabolism & Toxicology 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 C8H6ClF3, HPLC of Formula: 377727-87-2.

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

Lee, Sunghun published the artcileDeep-blue phosphorescence from perfluoro carbonyl-substituted iridium complexes, Safety of 2-[5-(Trifluoromethyl)-1H-1,2,4-triazol-3-yl]pyridine, the publication is Journal of the American Chemical Society (2013), 135(38), 14321-14328, database is CAplus and MEDLINE.

The new deep-blue iridium-(III) complexes, (TF)₂Ir-(pic), (TF)₂Ir-(fptz), (HF)₂Ir-(pic), and (HF)₂Ir-(fptz), consisting of 2′,4”-difluororphenyl-3-methylpyridine with trifluoromethyl carbonyl or heptafluoropropyl carbonyl at the 3′ position as the main ligand and a picolinate or a trifluoromethylated-triazole as the ancillary ligand, were synthesized and characterized for applications in organic light-emitting diodes (OLEDs). D. function theory (DFT) calculations showed that these iridium complexes had a wide band gap, owing to the introduction of the strong electron withdrawing perfluoro carbonyl group. Time-dependent DFT (TD-DFT) calculations suggested that their lowest triplet excited state was dominated by a HOMO → LUMO transition and that the contribution of the metal-to-ligand charge transfer (MLCT) was higher than 34% for all four complexes, indicating that strong spin-orbit coupling exists in the complexes. The 10 wt % (TF)₂Ir-(pic) doped 9-(3-(9H-carbazole-9-yl)-phenyl)-3-(dibromophenylphosphoryl)-9H-carbazole (mCPPO1) film exhibited the highest photoluminescence quantum yield of 74 ± 3% among the films based on the four complexes. Phosphorescent OLEDs based on (TF)₂Ir-(pic) and (TF)₂Ir-(fptz) exhibited maximum external quantum efficiencies of 17.1% and 8.4% and Commission Internationale de l’Eclairage (CIE) coordinates of (0.141, 0.158) and (0.147, 0.116), resp. These CIE coordinates represent some of the deepest blue emissions ever achieved from phosphorescent OLEDs with considerably high EQEs.

Journal of the American Chemical Society 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, Safety of 2-[5-(Trifluoromethyl)-1H-1,2,4-triazol-3-yl]pyridine.

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

Sohn, Sunyoung published the artcileSynthesis and characterization of heptaflurosulfonyl-substituted iridium complexes for blue phosphorescent organic light emitting diodes, Recommanded Product: 2-[5-(Trifluoromethyl)-1H-1,2,4-triazol-3-yl]pyridine, the publication is Molecular Crystals and Liquid Crystals (2018), 676(1), 83-94, database is CAplus.

We synthesized the heptaflurosulfonyl-substituted iridium complexes with SOCF₇pic, SOCF₇mpic, and SOCF₇taz as a dopants for blue phosphorescent organic light emitting diodes (PHOLEDs). The SOCF₇pic, SOCF₇mpic, and SOCF₇taz showed high thermal stability with thermal decomposition temperature of 395, 396, and 411 °C by the TGA measurement. Using newly synthesized dopants, blue emissive PHOLEDs were fabricated by using co-host materials during vacuum process. The devices with SOCF₇pic or SOCF₇mpic dopant exhibited similar current efficiencies (1.55 cd/A vs. 1.25 cd/A) and power efficiencies (1.24 lm/W vs. 1.0 lm/W). It showed relatively higher than the SOCF₇taz doped device efficiencies with 1.0 cd/A and 0.6 lm/W. The high efficiencies of the SOCF₇pic and SOCF₇mpic doped devices compared with the SOCF₇taz doped device are caused by the improved electrons and holes injection into the emitting layer with well-aligned HOMO-LUMO levels or relatively uniform surface morphol.

Molecular Crystals and Liquid Crystals 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 C12H15NO, Recommanded Product: 2-[5-(Trifluoromethyl)-1H-1,2,4-triazol-3-yl]pyridine.

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

Park, Hea Jung published the artcileRational Design, Synthesis, and Characterization of Deep Blue Phosphorescent Ir(III) Complexes Containing (4′-Substituted-2′-pyridyl)-1,2,4-triazole Ancillary Ligands, Application In Synthesis of 219508-27-7, the publication is Journal of Organic Chemistry (2013), 78(16), 8054-8064, database is CAplus and MEDLINE.

On the basis of the results of frontier orbital considerations, 4-substituted-2′-pyridyltriazoles were designed to serve as ancillary ligands in 2-phenylpyridine main ligand containing heteroleptic iridium(III) complexes that display deep blue phosphorescence emission. The iridium(III) complexes, Ir1–Ir7, prepared using the new ancillary ligands, were found to display structured, highly quantum efficient (Φ_p = 0.20-0.42) phosphorescence with emission maxima in the blue to deep blue 448-456 nm at room temperature In accord with predictions based on frontier orbital considerations, the complexes were observed to have emission properties that are dependent on the electronic nature of substituents at the C-4 position of the pyridine moiety of the ancillary ligand. Importantly, placement of an electron-donating Me group at C-4′ of the pyridine ring of the 5-(pyridine-2′-yl)-3-trifluoromethyl-1,2,4-triazole ancillary ligand leads to an iridium(III) complex that displays a deep blue phosphorescence emission maximum at 448 nm in both the liquid and film states at room temperature Finally, an OLED device, constructed using an Ir-complex containing the optimized ancillary ligand as the dopant, was found to emit deep blue color with a CIE of 0.15, 0.18, which is close to the perfect goal of 0.15, 0.15.

Journal of Organic 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, Application In Synthesis of 219508-27-7.

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

Jang, Jae-Ho published the artcileBlue-green phosphorescent imidazole-based iridium(III) complex with a broad full width at half maximum for solution-processed organic light-emitting diodes, Safety of 2-[5-(Trifluoromethyl)-1H-1,2,4-triazol-3-yl]pyridine, the publication is Synthetic Metals (2015), 180-186, database is CAplus.

A blue-green phosphorescent Ir(III) complex was designed and synthesized for solution-processed organic LEDs (OLEDs), (DMDPI)₂Ir(tftap), that contains 1,2-dimethyl-4,5-diphenyl-1H-imidazole (DMDPI) as the main ligand and 2-(3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl)pyridine (tftap) as an ancillary ligand. (DMDPI)₂Ir(tftap) showed good solubility in common organic solvents such as CH₂Cl₂, CHCl₃, toluene, and chlorobenzene. The luminescence (PL) of (DMDPI)₂Ir(tftap) showed a maximum emission peak (λ_max) of 532 nm in CH₂Cl₂ solution The HOMO and LUMO levels of (DMDPI)₂Ir(tftap) are -5.36 and -2.76 eV, resp. Solution-processed blue-green OLEDs were fabricated based on (DMDPI)₂Ir(tftap) with an ITO/PEDOT:PSS (30 nm)/26DCzPPy:(DMDPI)₂Ir(tftap) (11%) (40 nm)/TPBi (60 nm)/CsF (1 nm)/Al structure. The electroluminescent (EL) spectra of (DMDPI)₂Ir(tftap) exhibited a maximum emission peak at 522 nm with a broad full-width at half-maximum (FWHM) of 115 nm and Commission Internationale de L’Eclairage (CIE) coordinates of (0.33, 0.54) at 1000 cd m^-2. The device with 11% doping concentration of (DMDPI)₂Ir(tftap) exhibited a maximum luminance of 6304 cd m^-2, a maximum luminous efficiency of 7.14 cd A^-1, a power efficiency of 3.63 lm W^-1, and an external quantum efficiency of 2.59%. White-emitting devices containing a single emissive layer consisting of PVK as a polymer host, (DMDPI)₂Ir(tftap) as a blue-green dopant, and (PIQ)₂Ir(acac) as a red dopant were fabricated. These devices exhibited CIE coordinates of (0.42, 0.48) at 1000 cd m^-2, which are close to the standard warm white-light CIE coordinates of (0.44, 0.40).

Synthetic Metals 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, Safety of 2-[5-(Trifluoromethyl)-1H-1,2,4-triazol-3-yl]pyridine.

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

Hattori, Nobutaka published the artcileAdjunctive preladenant: A placebo-controlled, dose-finding study in Japanese patients with Parkinson’s disease., Application In Synthesis of 377727-87-2, the publication is Parkinsonism & related disorders (2016), 73-79, database is MEDLINE.

BACKGROUND: Preladenant, an adenosine 2A antagonist, reduced daily OFF time when administered as adjunctive treatment in a previous phase 2 trial in non-Japanese Parkinson’s disease (PD) patients on stable doses of levodopa. This study aimed to evaluate preladenant as adjunctive therapy in Japanese patients with PD. METHODS: In this randomized, placebo-controlled, double-blind, 12-week, dose-ranging, phase 2 study, Japanese patients with moderate to severe PD on a stable regimen of levodopa were randomly assigned 1:1:1:1 to preladenant 2 mg, 5 mg, or 10 mg BID or placebo. The primary efficacy end point was change from baseline to week 12 in mean OFF time, recorded using a PD diary. Safety and tolerability were also assessed. RESULTS: In total, 111 patients were randomly assigned to receive preladenant 2 mg, and 113 each received preladenant 5 mg, 10 mg, or placebo. In contrast to previous data, preladenant in this study did not demonstrate statistically significant efficacy; the primary outcome was -0.7 h (P = 0.0564), -0.5 h (P = 0.1844), and -0.3 h (P = 0.3386), respectively, for preladenant 2 mg, 5 mg, and 10 mg BID versus placebo. Overall, preladenant was well tolerated, and the frequency of adverse events appeared to be dose related. CONCLUSIONS: In this phase 2 study, preladenant used as adjunctive therapy in PD patients on stable doses of levodopa did not reduce mean OFF time; treatment was well tolerated at doses between 2 and 10 mg BID.

Parkinsonism & related disorders 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