Category: Triazoles

Al-Azmi, Amal published the artcileAlkylation of azoles: synthesis of new heterocyclic-based AT₁-non-peptide angiotensin (II) receptor antagonists, COA of Formula: C4HN5, the publication is Journal of Heterocyclic Chemistry (2007), 44(3), 515-520, database is CAplus.

Several analogs of Losartan (I) were synthesized as potential non-peptide angiotensin (II) receptor antagonists. In these non-peptide analogs, e.g., II, the tetrazole and the substituted imidazole rings of Losartan were replaced, resp., by a carboxylic acid function or its Me ester and substituted triazole, imidazole or benzimidazole moieties. The biphenyl bromide precursor (BPE) used to introduce the linker between the acid/ester function and the heterocyclic moiety was synthesized using Suzuki biphenyl coupling and then incorporated into the target mol. by simple nucleophilic substitution. The fixed N-aryl isomeric forms of several azole and benzimidazole tautomers were successfully separated by HPLC using 50% aqueous acetonitrile as eluent. Intermediate reaction products and final target compounds were fully characterized spectroscopically.

Journal of Heterocyclic Chemistry 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, COA of Formula: C4HN5.

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

Maalouf, M. published the artcileStudy of proton conductivity of triazole-based electrolytes for high temperature fuel cell applications, Recommanded Product: 1H-1,2,3-Triazole-4,5-dicarbonitrile, the publication is ECS Transactions (2010), 25(33), 19-25, database is CAplus.

4,5-Dicyano-1H-[1,2,3]-Triazole (DCTz) is a possible water replacement for proton transport in high temperature polymer electrolyte membranes since it exhibits a favorable proton affinity. In this study, some properties of DCTz doped with Trifluoromethanesulfonic Acid (TFMSA) and Heptadecafluorooctanesulfonic acid (C₈HO₃F₁₇S-HDSA) are investigated. Thermal anal. as well as FTIR data indicated the formation of the salts. After proving to be stable up to 140°C, DCTz, DCTz_TFMSA and DCTz_HDSA salts were formed into membranes in a Polyacrylonitrile (PAN) polymeric binder. Thermogravimetric anal. (TGA) showed that adding the acid increases the stability of the membranes. Electrochem. measurements showed that the acid loading increases the conductivity of these polymeric membranes. Thus, a DCTZ_TFMSA doped PAN membrane has higher conductivity than a DCTZ doped PAN membrane over a temperature range of 20°C to 160°C at low relative humidity (RH). Similarly, increasing the weight % of DCTz_TFMSA in PAN membranes leads to an improved conductivity by an order of magnitude.

ECS Transactions 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, Recommanded Product: 1H-1,2,3-Triazole-4,5-dicarbonitrile.

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

Subbaraman, R. published the artcileTriazole and triazole derivatives as proton transport facilitators in polymer electrolyte membrane fuel cells, Category: triazoles, the publication is Solid State Ionics (2009), 180(20-22), 1143-1150, database is CAplus.

Some basic aspects pertaining to the application of triazole and its derivatives as proton transport facilitators for membranes for high temperature fuel cell operations are investigated. Performance as proton transport facilitators is studied for compounds in their native solid state and as a dopant in a polymer membrane. Some key parameters which influence the proton transport in the system are the proton affinity, pKa or acidity, activation energy and the ease of formation of hydrogen bonding network. Theor. calculations of the proton affinity of the compounds are presented. The effect of proton affinity of the compound on the activation energies for proton transport is investigated. Proton conductivity is measured for acid doped triazoles in both pellet form (powder triazole mixed with acid) and in composite forms wherein the acid group is contained in a polymer matrix. The effect of formation of a hydrogen bonding network by the triazoles and its impact on the proton conductivity are studied. Also, the effect of ion exchange capacity (IEC) of the host polymeric electrolytes and loading of triazoles in the composites were investigated.

Solid State Ionics 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 C16H24BF4Ir, Category: triazoles.

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

Subbaraman, R. published the artcileTriazole and triazole derivatives as proton transport facilitators in polymer electrolyte membrane fuel cells, SDS of cas: 53817-16-6, the publication is Solid State Ionics (2009), 180(20-22), 1143-1150, database is CAplus.

Some basic aspects pertaining to the application of triazole and its derivatives as proton transport facilitators for membranes for high temperature fuel cell operations are investigated. Performance as proton transport facilitators is studied for compounds in their native solid state and as a dopant in a polymer membrane. Some key parameters which influence the proton transport in the system are the proton affinity, pKa or acidity, activation energy and the ease of formation of hydrogen bonding network. Theor. calculations of the proton affinity of the compounds are presented. The effect of proton affinity of the compound on the activation energies for proton transport is investigated. Proton conductivity is measured for acid doped triazoles in both pellet form (powder triazole mixed with acid) and in composite forms wherein the acid group is contained in a polymer matrix. The effect of formation of a hydrogen bonding network by the triazoles and its impact on the proton conductivity are studied. Also, the effect of ion exchange capacity (IEC) of the host polymeric electrolytes and loading of triazoles in the composites were investigated.

Solid State Ionics 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 C14H10N2O, SDS of cas: 53817-16-6.

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

Subbaraman, Ram published the artcile4,5-Dicyano-1H-[1,2,3]-Triazole as a Proton Transport Facilitator for Polymer Electrolyte Membrane Fuel Cells, Name: 1H-1,2,3-Triazole-4,5-dicarbonitrile, the publication is Journal of the American Chemical Society (2007), 129(8), 2238-2239, database is CAplus and MEDLINE.

High proton conductivity with limited or no dependence on humidity is the desired property for proton exchange membrane for use in a fuel cell operating >100°. Proton exchange facilitators are designed to aid in transport of protons at low humidity conditions by acting as a proton bridge. The presence of intermol. hydrogen bonding in these compounds gives a proton conducting network where the proton hopping is enabled by the amphoteric nature of these neutral mols. The authors report 4,5-dicyano-1H-[1,2,3]-triazole (DCTz) as an active proton transport facilitator for PEM fuel cells. The authors observe conductivities ∼1 mS/cm in dry conditions at 100° for composites of DCTz with polyacrylonitrile in the absence of any external proton sources. High acidity of N-H proton as well as existence of a hydrogen-bonded network in DCTz leads to facile proton transport through the membrane in the absence of humidity. Diffusion measurements from NMR experiments further confirm the existence of local proton conducting structures over the long range. Electrochem. stability of DCTz in the potential window of interest offers addnl. advantage for the use of this material in PEM fuel cells.

Journal of the American Chemical Society 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 C12H19BrS, Name: 1H-1,2,3-Triazole-4,5-dicarbonitrile.

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

Zhang, Xueli published the artcileA simple, fast and convenient new method for predicting the stability of nitro compounds, Product Details of C2H2N4O2, the publication is Journal of Computer-Aided Molecular Design (2015), 29(5), 471-483, database is CAplus and MEDLINE.

A new method has been proposed to understand and predict the stability of nitro compounds This method uses the maximum electron densities at the critical points of two N-O bonds of nitro groups (ρ_max), and it is more simple and faster than the existing methods and applicable to bigger systems. The correlations between the ρ_max and total energy (E), bond lengths (R_C-NO2, R_N-NO2 and R_O-NO2), bond dissociation energy (BDE), and impact sensitivity (h₅₀) reveal that the mol. stability, which can be reflected by E, R, BDE and h₅₀, generally decreases with the increasing ρ_max. The compound with the larger ρ_max is less stable. For the nitrating reaction, the smaller ρ_max of the product generally implies the easier and faster reaction and the higher occurrence ratio of the product. Therefore, ρ_max can be applied to predict the stability of nitro compounds and the easiness of the nitrating reaction.

Journal of Computer-Aided Molecular Design 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 C12H23N3S, Product Details of C2H2N4O2.

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

Sirci, Francesco published the artcileLigand-, structure- and pharmacophore-based molecular fingerprints: a case study on adenosine A₁, A_2A, A_2B, and A₃ receptor antagonists, Safety of 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 Journal of Computer-Aided Molecular Design (2012), 26(11), 1247-1266, database is CAplus and MEDLINE.

FLAP fingerprints are applied in the ligand-, structure- and pharmacophore-based mode in a case study on antagonists of all four adenosine receptor (AR) subtypes. Structurally diverse antagonist collections with respect to the different ARs were constructed by including binding data to human species only. FLAP models well discriminate “active” (=highly potent) from “inactive” (=weakly potent) AR antagonists, as indicated by enrichment curves, numbers of false positives, and AUC values. For all FLAP modes, model predictivity slightly decreases as follows: A_2BR > A_2AR > A₃R > A₁R antagonists. General performance of FLAP modes in this study is: ligand- > structure- > pharmacophore- based mode. We also compared the FLAP performance with other common ligand- and structure-based fingerprints. Concerning the ligand-based mode, FLAP model performance is superior to ECFP4 and ROCS for all AR subtypes. Although focusing on the early first part of the A_2A, A_2B and A₃ enrichment curves, ECFP4 and ROCS still retain a satisfactory retrieval of actives. FLAP is also superior when comparing the structure-based mode with PLANTS and GOLD. In this study we applied for the first time the novel FLAPPharm tool for pharmacophore generation. Pharmacophore hypotheses, generated with this tool, convincingly match with formerly published data. Finally, we could demonstrate the capability of FLAP models to uncover selectivity aspects although single AR subtype models were not trained for this purpose.

Journal of Computer-Aided Molecular Design 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 C8H14O2, Safety of 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

Gyoneva, Stefka published the artcileSystemic inflammation regulates microglial responses to tissue damage in vivo., Synthetic Route of 377727-87-2, the publication is Glia (2014), 62(8), 1345-60, database is MEDLINE.

Microglia, the resident immune cells of the central nervous system, exist in either a “resting” state associated with physiological tissue surveillance or an “activated” state in neuroinflammation. We recently showed that ATP is the primary chemoattractor to tissue damage in vivo and elicits opposite effects on the motility of activated microglia in vitro through activation of adenosine A2A receptors. However, whether systemic inflammation affects microglial responses to tissue damage in vivo remains largely unknown. Using in vivo two-photon imaging of mice, we show that injection of lipopolysaccharide (LPS) at levels that can produce both clear neuroinflammation and some features of sepsis significantly reduced the rate of microglial response to laser-induced ablation injury in vivo. Under proinflammatory conditions, microglial processes initially retracted from the ablation site, but subsequently moved toward and engulfed the damaged area. Analyzing the process dynamics in 3D cultures of primary microglia indicated that only A2A , but not A1 or A3 receptors, mediate process retraction in LPS-activated microglia. The A2A receptor antagonists caffeine and preladenant reduced adenosine-mediated process retraction in activated microglia in vitro. Finally, administration of preladenant before induction of laser ablation in vivo accelerated the microglial response to injury following systemic inflammation. The regulation of rapid microglial responses to sites of injury by A2A receptors could have implications for their ability to respond to the neuronal death occurring under conditions of neuroinflammation in neurodegenerative disorders.

Glia 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, Synthetic Route of 377727-87-2.

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

Del Valle, J. C. published the artcileA theoretical study of the acidity of nitrogen heterocycles, Formula: C2H3N3, the publication is Journal of Molecular Structure: THEOCHEM (1992), 481-91, database is CAplus.

INDO and AM1 calculations of C-H and N-H deprotonation (acidity) of 20 nitrogen heterocycles were performed. Acidity is explained by taking into account lone pair repulsion, aza, and annelation effects. The AM1 method has to be corrected by adding 9 kcal mol^-1 for each adjacent lone pair-lone pair interaction.

Journal of Molecular Structure: THEOCHEM 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, Formula: C2H3N3.

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

Mo, O. published the artcileProtonation energies and tautomerism of azoles. Basis set effects, HPLC of Formula: 63598-71-0, the publication is Journal of Physical Chemistry (1986), 90(22), 5597-604, database is CAplus.

The structure, protonation energies, tautomerism, and vertical ionization potentials of several azoles are examined by ab initio calculations using different basis sets ranging from minimal to split valence plus polarization. Minimal basis tends to overestimate all N-N and C-N lengths. Though, in general, 3-21G geometries are close to 6-31G structures, the former basis does not always correct the deficiencies of minimal basis. In general, 6-31G structures agree with the exptl. ones. Azoles with more than one basic N atom protonate preferentially on imidazolic rather than on pyrazolic type N atoms. Minimal basis significantly overestimates absolute protonation energies, but the deviations observed for relative protonation energies are not always of the same sign. Both 3-21G and 6-31G absolute protonation energies are almost equal and much smaller than those obtained at the minimal basis level. The inclusion of polarization functions in the basis (6-31G^*//6-31G calculations) leads to a further decrease in absolute protonation energies which depends on the degree of anisotropy of the charge distribution of the center which undergoes protonation. The relative stabilities of the tautomers change with the basis set. These changes are particularly important for triazolium and tetrazolium cations, as well as for pyrazole and imidazole. For 1,2,4-triazoles, tetrazoles, and 1H-pentazole Koopman’s theorem predicts the wrong ionization potential.

Journal of Physical 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, HPLC of Formula: 63598-71-0.

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