Category: Triazoles

Gamezo, V. N. published the artcileTheoretical analysis of the effects of nitration of the explosive properties of triazoles: 4-nitro-2H-1,2,3-triazole and 4,5-dinitro-2H-1,2,3-triazole, Quality Control of 84406-63-3, the publication is Journal of Molecular Structure: THEOCHEM (1995), 337(2), 189-97, database is CAplus.

At the mol. level, the ground-state intrinsic energies of the C-NO₂ and N-N bonds and the excited-state bond polarities of the 4-nitro- and 4,5-dinitro-2H-1,2,3-triazoles were compared using their theor. optimized geometries. Their enthalpies of formation were calculated using a modified Xα approach; finally, their explosive characteristics were studied at the macroscopic level with the help of the thermodn. code of Kondrikov-Sumin. With respect to the planar mononitro derivative, the second nitration provokes: (1) a torsion of ∼30° of the two nitro groups, (2) a significantly decreased C-N bond dissociation energy, by ∼9 kcal/mol, together with a weakening of the N-N bonds, thus reducing thermal stability, (3) an increase of C-NO₂ and N-N bond polarities in the electronically excited states, correlated with a decreased shock sensitivity, and (4) an increase in gas-phase enthalpy of formation, from -25 kcal/mol (or -51 kcal/mol, estimated for the condensed phase) for the mononitro derivative to +65 kcal/mol (e.g., +50 kcal/mol) for the dinitro compound Using these enthalpy results and a Kondrikov-Sumin-like equation of state, one can describe the ideal velocity of detonation D_CJ as a function of the d. ρ₀ by D_CJ = 0.337 + 3.86ρ₀ ,and D_CJ = 2.246 + 3.61ρ₀ for the mononitro and dinitro derivatives, resp., thus giving the corresponding detonation velocities of 6.5 and 8.0 km/s for an assumed d. of 1.6 g/m³.

Journal of Molecular Structure: THEOCHEM 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, Quality Control of 84406-63-3.

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

Nichols, Charles M. published the artcileGas-Phase Acidities of Nitrated Azoles as Determined by the Extended Kinetic Method and Computations, Application In Synthesis of 84406-63-3, the publication is Journal of Physical Chemistry A (2015), 119(2), 395-402, database is CAplus and MEDLINE.

Making use of the extended kinetic method and the alternative method for data anal., we have exptl. determined ΔH°_acid (kcal/mol) for six mononitrated azole species (2-nitropyrrole = 337.0, 3-nitropyrrole = 335.8, 3-nitropyrazole = 330.5, 4-nitropyrazole = 329.5, 2-nitroimidazole = 327.4, and 4-nitroimidazole = 325.0). We report an absolute uncertainty of ±2.2 kcal/mol that arises from the uncertainties of the reference acids; the relative values are known within 0.4 kcal/mol. Combining these exptl. ΔH°_acid values with ΔS°_acid values calculated at the B3LYP/aug-cc-pVTZ level of theory, we report ΔG°_acid (kcal/mol) for the nitroazoles (2-nitropyrrole = 329.4, 3-nitropyrrole = 328.4, 3-nitropyrazole = 323.1, 4-nitropyrazole = 322.0, 2-nitroimidazole = 319.7, and 4-nitroimidazole = 317.6); the absolute uncertainties are ±2.4 kcal/mol. In addition to the exptl. studies, we have computationally investigated the gas-phase acidities and electron affinities of the azoles in this work, as well as higher-order aza- and dinitro-substituted azoles. We discuss trends in the stabilities of the deprotonated azoles based on aza substitution and nitro group placement. 4-Nitroimidazole has already found use as the anionic component in ionic liquids, and we propose that the addnl. nitrated azolate ions are potential candidates for the anionic component of ionic liquids

Journal of Physical Chemistry A 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, Application In Synthesis of 84406-63-3.

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

Trifonov, R. E. published the artcileBasicity of 1,2,3-triazole and some of its derivatives, Application of 5-Nitro-1H-1,2,3-triazole, the publication is Zhurnal Organicheskoi Khimii (1995), 31(6), 928-33, database is CAplus.

The following pK_BH⁺ values were found: 1,2,3-triazole, -0.16; 4-nitro-1,2,3-triazole, -6.80; 1-phenyl-1,2,3-triazole, -0.11; 2-phenyl-1,2,3-triazole, -5.21; 4-phenyl-1,2,3-triazole, -5.36. The values for the phenyl-1,2,3-triazoles were discussed in terms of the structure of the conjugate acids and nπ-interactions.

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 C6H8N2, Application of 5-Nitro-1H-1,2,3-triazole.

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

Krygowski, Tadeusz M. published the artcileSigma- and pi-electron structure of aza-azoles, Category: triazoles, the publication is Journal of Molecular Modeling (2011), 17(6), 1427-1433, database is CAplus and MEDLINE.

The reasons behind changes of aromaticity in 10 unsubstituted aza-azoles were analyzed by employing the natural bond orbital (NBO) approach at the MP2/6-311+G(d,p) level of theory. Sum of occupations of p_z orbitals at atoms in the ring correlates well with the magnetism based aromaticity index NICS as well as with the number of nitrogen atoms in the ring. Changes of NICS depend strongly in a linear way on the number of NN bonds. Classification of azoles based on the number of pyridine-type nitrogen atoms vicinal to NH is supported by plotting the relative occupation of π orbitals (π_occ) against the relative occupation of σ orbitals (σ_occ) for all individual atoms in rings.

Journal of Molecular Modeling 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, Category: triazoles.

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

Tran, Kim T. published the artcileA Comparative Assessment Study of Known Small-Molecule Keap1-Nrf2 Protein-Protein Interaction Inhibitors: Chemical Synthesis, Binding Properties, and Cellular Activity, HPLC of Formula: 1799973-82-2, the publication is Journal of Medicinal Chemistry (2019), 62(17), 8028-8052, database is CAplus and MEDLINE.

Inhibiting the protein-protein interaction (PPI) between the transcription factor Nrf2 and its repressor protein Keap1 has emerged as a promising strategy to target oxidative stress in diseases, including central nervous system (CNS) disorders. Numerous non-covalent small-mol. Keap1-Nrf2 PPI inhibitors have been reported to date, but many feature suboptimal physicochem. properties for permeating the blood-brain barrier, while others contain problematic structural moieties. Here, we present the first side-by-side assessment of all reported Keap1-Nrf2 PPI inhibitor classes using fluorescence polarization, thermal shift assay, and surface plasmon resonance-and further evaluate the compounds in an NQO1 induction cell assay and in counter tests for nonspecific activities. Surprisingly, half of the compounds were inactive or deviated substantially from reported activities, while we confirm the cross-assay activities for others. Through this study, we have identified the most promising Keap1-Nrf2 inhibitors that can serve as pharmacol. probes or starting points for developing CNS-active Keap1 inhibitors.

Journal of Medicinal Chemistry published new progress about 1799973-82-2. 1799973-82-2 belongs to triazoles, auxiliary class Other Aromatic Heterocyclic,Bromide,Ether, name is 5-Bromo-7-methoxy-1-methyl-1H-benzo[d][1,2,3]triazole, and the molecular formula is C4H3Cl2N3, HPLC of Formula: 1799973-82-2.

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

Catalan, J. published the artcileOn the acidity and basicity of azoles: the Taft scheme for electrostatic proximity effects, Synthetic Route of 63598-71-0, the publication is International Journal of Mass Spectrometry and Ion Processes (1998), 175(1,2), 51-59, database is CAplus.

A theor. study of the acid-base behavior of azole systems was carried out using d. functional theory (B3LYP). The results were consistent with exptl. measurements of the systems in the gas phase. A 2-way linear relationship between theor. and exptl. data is established that links the acid and base ranges for the neutral forms. The applicability of the Taft model for electrostatic proximity effects to this type of compounds is shown.

International Journal of Mass Spectrometry and Ion Processes 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, Synthetic Route of 63598-71-0.

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

Saini, Anjali published the artcileAdenosine receptor antagonists: Recent advances and therapeutic perspective, Recommanded Product: 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, the publication is European Journal of Medicinal Chemistry (2022), 113907, database is CAplus and MEDLINE.

A review. Adenosine is an endogenous purine-based nucleoside expressed nearly in all body tissues. It regulates various body functions by activating four G-protein coupled receptors, A1, A2A, A2B, and A3. These receptors are widely acknowledged as drug targets for treating different neurol., metabolic, and inflammatory diseases. Although numerous adenosine receptor inhibitors have been developed worldwide, achieving target selectivity is still a big hurdle in drug development. However, the identification of specific radioligands-based affinity assay, fluorescent ligands, and MS-based ligand assay have contributed to the development of selective and potent adenosine ligands. In recent years various small heterocyclic-based mols. have shown some promising results. Istradefylline has been approved for treating Parkinson’s in Japan, while preladenant, tozadenant, CVT-6883, MRS-1523, and many more are under different phases of clin. development. The present review is focused on the quest to develop potent and selective adenosine inhibitors from 2013 to early 2021 by various research groups. The review also highlights their biol. activity, selectivity, structure-activity relationship, mol. docking, and mechanistic studies. A special emphsesis on drug designing strategies has been also given the manuscript. The comprehensive compilation of research work carried out in the field will provide inevitable scope for designing and developing novel adenosine inhibitors with improved selectivity and efficacy.

European 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, Recommanded Product: 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.

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

Hebert, T. J. published the artcileThe influence of solvent upon the optical rotation of diethyl tartrate, Synthetic Route of 53817-16-6, the publication is Proceedings of the Iowa Academy of Science (1927), 218-9, database is CAplus.

Determination, of the [α] of di-Et tartrate in various mixed solvents have been made at 25° and 30°, with 2 different concentrations of the ester. The solvents used were EtOH, MeOH, C₆H₆ and PhMe and the binary mixtures of each solvent with each of the remaining solvents. The mixed solvents were made on a mol. fraction basis. The [α] was found to be dependent on the composition of the mixed solvent, upon the concentration of the ester and upon the temperature It was also found to be influenced by the nature and proportions of the 2 solvents forming the binary mixture

Proceedings of the Iowa Academy of Science 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, Synthetic Route of 53817-16-6.

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

Xu, Huixia published the artcileSynthesis and photoelectric performances of blue-green emitting iridium phenylpyridine complexes using N,N’-heteroaromatic ancillary ligands, Computed Properties of 219508-27-7, the publication is New Journal of Chemistry (2015), 39(7), 5293-5299, database is CAplus.

Four iridium complexes [(ppy)₂IrL] containing different ancillary ligands [HL = 2-(5-R-2H-1,2,4-triazol-3-yl)pyridine, where R = 4-CF₃C₆H₄ (Htfmpptz), 4-FC₆H₄ (Hfpptz), CF₃ (Htfmptz); Hppy = 2-phenylpyridine] were synthesized and characterized. Their mol. structures were identified by x-ray single crystal diffraction. The effects of ancillary ligands on the photophys. and luminescence behaviors were investigated. The emission maximum peaks of (ppy)₂Ir(tfmpptz), (ppy)₂Ir(fpptz) and (ppy)₂Ir(tfmptz) in CH₂Cl₂ solution appear at 485, 487 and 483 nm, resp. Phosphorescent organic light-emitting devices (PhOLEDs) were fabricated using these complexes doped in CBP as an emitting layer.

New Journal of 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 C7H8O3, Computed Properties of 219508-27-7.

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

Rascol, Olivier published the artcileNew treatments for levodopa-induced motor complications, Category: triazoles, the publication is Movement Disorders (2015), 30(11), 1451-1460, database is CAplus and MEDLINE.

A review. Levodopa (L-dopa)-induced motor complications, including motor fluctuations and dyskinesia, affect almost all patients with Parkinson’s disease (PD) at some point during the disease course, with relevant implications in global health status. Various dopaminergic and nondopaminergic pharmacol. approaches as well as more invasive strategies including devices and functional surgery are available to manage such complications. In spite of undisputable improvements during the last decades, many patients remain significantly disabled, and a fully satisfying management of L-dopa-induced motor complications is still an important unmet need of PD therapy. This article reviews the recent trial results published from 2013 to Apr. 2015 about pharmacol. and nonpharmacol. interventions to treat motor complications. Randomized controlled trials conducted in patients suffering from already established complications showed that new levodopa (L-dopa) formulations such as intrajejunal L-dopa-carbidopa infusion and bilayered extended-release L-dopa-carbidopa (IPX066) can improve motor fluctuations. Pos. results were also obtained with a new monoamine oxidase B (MAO-B) inhibitor (safinamide) and a catechol-O-methyltransferase COMT inhibitor (opicapone). Pilot data suggest that new formulations of dopamine agonists (inhaled apomorphine) are also of potential interest. The development of novel nondopaminergic adenosine A2A antagonists (istradefylline, preladenant, and tozadenant) to treat motor fluctuations showed conflicting results in phase 2 and phase 3 trials. For dyskinesia, trials with new amantadine extended-release formulations confirmed the interest of the glutamatergic N-methyl-L-aspartate (NMDA) antagonist approach. Pos. pilot antidyskinetic effects were also recently reported using serotonin agents such as eltoprazine and glutamate mGluR5 modulators such as mavoglurant. However, the translation to clin. practice of such innovative concepts remains challenging, because subsequent phase 2 trials conducted to confirm the antidyskynetic effects of mavoglurant failed, leading to the interruption of the development of this compound for this indication. © 2015 International Parkinson and Movement Disorder Society.

Movement 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, Category: triazoles.

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