Category: Triazoles

Vasiliu, Monica published the artcileComputational Studies of the Properties of Azole·xBH₃ Adducts for Chemical Hydrogen Storage Systems, Application In Synthesis of 63598-71-0, the publication is Journal of Physical Chemistry C (2012), 116(42), 22196-22211, database is CAplus.

The thermodn. properties of the potential hydrogen storage compounds, the borane adducts of pyrrole, pyrazole, imidazole, triazole, and tetrazole, were calculated at the G3MP2 level by using an isodesmic approach including exptl. and accurate (CCSD(T)/CBS) values for the other components of the reaction. The heats of formation, bond dissociation energies, dehydrogenation energies, proton affinities, gas phase acidities, pK_as in aqueous solution, and hydride affinities were calculated The H₃B-N dative bonds to an sp² nitrogen are much stronger than those to an sp³ nitrogen for the 5-member rings. The dehydrogenation energies at the sp³ nitrogen for the azole borane adducts are exothermic and those at the sp² nitrogen borane adducts are closer to thermo-neutral (-7.7 to +9.4 kcal/mol). The gas phase acidity decreases (becomes more acidic) with increasing the number of the nitrogen atoms in the 5-member heterocycle and with increasing the number of coordinated BH₃ mols. to the azole nitrogens. The pK_a values show that the azole borane adducts are strong to very strong acids with the 1,2,5-triboryl-1,2,3,4-tetrazole, predicted to be even stronger than the strongest known acid (CF₃SO₂)₂CH. The hydride affinities of the azole borane adducts show that they are stronger Lewis acids than BH₃.

Journal of Physical Chemistry C 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 C17H29BO2, Application In Synthesis of 63598-71-0.

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

Mittapelli, Vasantha published the artcileIsolation/synthesis & characterization & potential impurities of antifungal drug, Fluconazole, Quality Control of 86386-77-8, the publication is Asian Journal of Biochemical and Pharmaceutical Research (2011), 1(4), 201-206, database is CAplus.

In the synthesis of Fluconazole in bulk [α-(2,4-difluorophenyl)-α-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazole-1-ethanol] various impurities are formed. The synthesis of the target compounds was achieved by a literature synthesis or using fluconazole as a starting material. The present work details the isolation/synthesis and characterization of isomer impurity, triazole impurity and desfluoro impurity [i.e., α-(4-fluorophenyl)-α-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazole-1-ethanol].

Asian Journal of Biochemical and Pharmaceutical Research 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

Zhou, Gang published the artcileDiscovery of aminoquinazoline derivatives as human A_2A adenosine 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 Bioorganic & Medicinal Chemistry Letters (2016), 26(4), 1348-1354, database is CAplus and MEDLINE.

Novel bicyclic adenosine A_2A antagonists with an aminoquinazoline moiety were designed and synthesized. The optimization of the initial lead compound based on in vitro and in vivo activity has led to the discovery of a potent and selective class of adenosine A_2A antagonists. The structure-activity relationships of this novel series of bicyclic aminoquinazoline derivatives as adenosine A_2A antagonists are described in detail.

Bioorganic & Medicinal Chemistry Letters 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 C21H18N4OS, 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

Orru, Marco published the artcileStriatal pre- and postsynaptic profile of adenosine A_2A receptor antagonists, SDS of cas: 377727-87-2, the publication is PLoS One (2011), 6(1), e16088, database is CAplus and MEDLINE.

Striatal adenosine A_2A receptors (A_2ARs) are highly expressed in medium spiny neurons (MSNs) of the indirect efferent pathway, where they heteromerize with dopamine D₂ receptors (D₂Rs). A_2ARs are also localized presynaptically in cortico-striatal glutamatergic terminals contacting MSNs of the direct efferent pathway, where they heteromerize with adenosine A₁ receptors (A₁Rs). It was hypothesized that postsynaptic A_2AR antagonists should be useful in Parkinson’s disease, while presynaptic A_2AR antagonists could be beneficial in dyskinetic disorders, such as Huntington’s disease, obsessive-compulsive disorders and drug addiction. The aim or this work was to determine whether selective A_2AR antagonists may be subdivided according to a preferential pre- vs. postsynaptic mechanism of action. The potency at blocking the motor output and striatal glutamate release induced by cortical elec. stimulation and the potency at inducing locomotor activation were used as in vivo measures of pre- and postsynaptic activities, resp. SCH-442416 and KW-6002 showed a significant preferential pre- and postsynaptic profile, resp., while the other tested compounds (MSX-2, SCH-420814, ZM-241385 and SCH-58261) showed no clear preference. Radioligand-binding experiments were performed in cells expressing A_2AR-D₂R and A₁R-A_2AR heteromers to determine possible differences in the affinity of these compounds for different A_2AR heteromers. Heteromerization played a key role in the presynaptic profile of SCH-442416, since it bound with much less affinity to A_2AR when co-expressed with D₂R than with A₁R. KW-6002 showed the best relative affinity for A_2AR co-expressed with D₂R than co-expressed with A₁R, which can at least partially explain the postsynaptic profile of this compound Also, the in vitro pharmacol. profile of MSX-2, SCH-420814, ZM-241385, and SCH-58261 was is in accordance with their mixed pre- and postsynaptic profile. On the basis of their preferential pre- vs. postsynaptic actions, SCH-442416 and KW-6002 may be used as lead compounds to obtain more effective antidyskinetic and antiparkinsonian compounds, resp.

PLoS One 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, SDS of cas: 377727-87-2.

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

Efimov, Ilya published the artcileReactions of β-Azolylenamines with Sulfonyl Azides as an Approach to N-Unsubstituted 1,2,3-Triazoles and Ethene-1,2-diamines, Application of 5-Nitro-1H-1,2,3-triazole, the publication is European Journal of Organic Chemistry (2014), 2014(17), 3684-3689, database is CAplus.

The reactions of β-azolylenamines with sulfonyl azides in acetonitrile furnished 1H-4-(azol-5-yl)-1,2,3-triazoles in yields of 52-93%. β-Benzoylenaminones and β-nitroenamine of type 1 also reacted with tosyl azide to form the same type of products 3, proving the generality and efficiency of the method for the synthesis of N-unsubstituted 1,2,3-triazoles. However, the reactions of 3-(1-aryl-1,2,3-triazol-5-yl)enamines with tosyl azide in the absence of a solvent afforded a mixture of (E)-1-dimethylamino-2-tosylaminoethenes and N,N-dimethyl-N’-tosylformamidine in yields of 40-50 and 20 %, resp. The formation of a variety of compounds from the reactions of enamines with sulfonyl azides is rationalized by the various possible transformations of the intermediate 5-dimethylamino-1,2,3-triazolines.

European Journal of Organic Chemistry 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, Application of 5-Nitro-1H-1,2,3-triazole.

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

Katritzky, Alan R. published the artcileAromaticity as a quantitative concept. 4. Less familiar five- and six-membered monocyclic heterocycles, Related Products of triazoles, the publication is Journal fuer Praktische Chemie (Leipzig) (1990), 332(6), 885-97, database is CAplus.

An addnl. set of 23 monoheterocycles was subjected to AM1 calculations, and the characteristics thus determined, together with available exptl. data were treated by PC anal. Utilizing characteristic loadings previously determined for other monoheterocycles, scores for the 23 monoheterocycles were deduced. The new scores correlate well with those previously found and with the chem. nature of the heterocycles. The dominant influence on the t₁ is the nature of the heteroatoms present, whereas the dominant influence on t₂ is the number of heteroatoms present. Pyridine-like nitrogen atoms have relatively little effect on classical aromaticity. Five-membered rings are less aromatic than six-membered, the presence of an oxygen atom has a particularly aromaticity-reducing effect, and the effect of sulfur is much less than oxygen and only a little more than nitrogen. The predictive power for the present compounds is limited by the relative paucity of and some problems with the input data but succeeds well for some parameters.

Journal fuer Praktische Chemie (Leipzig) 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, Related Products of triazoles.

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

Hodgson, Robert A. published the artcilePreladenant, a selective A_2A receptor antagonist, is active in primate models of movement disorders, Product Details of C25H29N9O3, the publication is Experimental Neurology (2010), 225(2), 384-390, database is CAplus and MEDLINE.

Parkinson’s Disease (PD) and Extrapyramidal Syndrome (EPS) are movement disorders that result from degeneration of the dopaminergic input to the striatum and chronic inhibition of striatal dopamine D₂ receptors by antipsychotics, resp. Adenosine A_2A receptors are selectively localized in the basal ganglia, primarily in the striatopallidal (“indirect”) pathway, where they appear to operate in concert with D₂ receptors and have been suggested to drive striatopallidal output balance. In cases of dopaminergic hypofunction, A_2A receptor activation contributes to the overdrive of the indirect pathway. A_2A receptor antagonists, therefore, have the potential to restore this inhibitor imbalance. Consequently, A_2A receptor antagonists have therapeutic potential in diseases of dopaminergic hypofunction such as PD and EPS. Targeting the A_2A receptor may also be a way to avoid the issues associated with direct dopamine agonists. Recently, preladenant was identified as a potent and highly selective A_2A receptor antagonist, and has produced a significant improvement in motor function in rodent models of PD. Here we investigate the effects of preladenant in two primate movement disorder models. In MPTP-treated cynomolgus monkeys, preladenant (1 or 3 mg/kg; PO) improved motor ability and did not evoke any dopaminergic-mediated dyskinetic or motor complications. In Cebus apella monkeys with a history of chronic haloperidol treatment, preladenant (0.3-3.0 mg/kg; PO) delayed the onset of EPS symptoms evoked by an acute haloperidol challenge. Collectively, these data support the use of preladenant for the treatment of PD and antipsychotic-induced movement disorders.

Experimental 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, Product Details of C25H29N9O3.

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

Dahmani, R. published the artcileInsights on the interaction of Zn^2 + cation with triazoles: Structures, bonding, electronic excitation and applications, Recommanded Product: 4H-1,2,4-Triazole, the publication is Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy (2018), 375-384, database is CAplus and MEDLINE.

At present, we investigate the structures, the stability, the bonding and the spectroscopy of the Zn²⁺-triazole complexes (Zn²⁺-Tz), which are subunits of triazolate based porous materials and Zn-enzymes. This theor. work is performed using ab initio methods and d. functional theory (DFT) where dispersion correction is included. Through these benchmarks, we establish the ability and reliability of M05-2X + D3 and PBE0 + D3 functionals for the correct description of Zn²⁺-Tz bond since these DFTs lead to close agreement with post Hartree-Fock methods. Therefore, M05-2X + D3 and PBE0 + D3 functionals are recommended for the characterization of larger organometallic complexes formed by Zn and N-rich linkers. For Zn²⁺-Tz, we found two stable σ-type complexes: (i) a planar structure where Zn²⁺ links to unprotonated nitrogen and (ii) an out-of-plane cluster where carbon interacts with Zn²⁺. The most stable isomers consist on a coordinated covalent bond between the lone pair of unprotonated nitrogen and the vacant 4s orbital of Zn²⁺. The roles of covalent interactions within these complexes are discussed after vibrational, NBO, NPA charges and orbital analyses. The bonding is dominated by charge transfer from Zn²⁺ to Tz and intramol. charge transfer, which plays a vital role for the catalytic activity of these complexes. These findings are important to understand, at the microscopic level, the structure and the bonding within triazolate based macromol. porous materials and Zn-enzymes.

Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy 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

Hodgson, Robert A. published the artcileCharacterization of the potent and highly selective A_2A receptor antagonists preladenant and SCH 412348 [7-[2-[4-2,4-difluorophenyl]-1-piperazinyl]ethyl]-2-(2-furanyl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine] in rodent models of movement disorders and depression, Name: 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 Pharmacology and Experimental Therapeutics (2009), 330(1), 294-303, database is CAplus and MEDLINE.

The adenosine A_2A receptor has been implicated in the underlying biol. of various neurol. and psychiatric disorders, including Parkinson’s disease (PD) and depression. Preladenant and SCH 412348 [7-[2-[4-2,4-difluorophenyl]-1-piperazinyl]ethyl]-2-(2-furanyl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine] are potent competitive antagonists of the human A_2A receptor (K_i = 1.1 and 0.6 nM, resp.) and have > 1000-fold selectivity over all other adenosine receptors, making these compounds the most selective A_2A receptor antagonists reported to date. Both compounds attenuate hypolocomotion induced by the A_2A receptor agonist CGS-21680 [2-[p-(2-carboxyethyl)phenethylamino]-5′-N-ethylcarboxamidoadenosine], suggesting that they inhibit A_2A receptor activity in vivo. Their high degree of selectivity and robust in vivo activity make preladenant and SCH 412348 useful tools to investigate the role of the A_2A receptor system in animal models of PD and depression. Oral administration of preladenant and SCH 412348 (0.1-1 mg/kg) to rats potentiated 3,4-dihydroxy-L-phenylalanine (L-Dopa)-induced contralateral rotations after 6-hydroxydopamine lesions in the medial forebrain bundle and potently attenuated the cataleptic effects of haloperidol. Preladenant (1 mg/kg) inhibited L-Dopa-induced behavioral sensitization after repeated daily administration, which suggests a reduced risk of the development of dyskinesias. Finally, preladenant and SCH 412348 exhibited antidepressant-like profiles in models of behavioral despair, namely the mouse tail suspension test and the mouse and rat forced swim test. These studies demonstrate that preladenant and SCH 412348 are potent and selective A_2A receptor antagonists and provide further evidence of the potential therapeutic benefits of A_2A receptor inhibition in PD (with reduced risk of dyskinesias) and depression (one of the primary nonmotor symptoms of PD).

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, Name: 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

Palmer, M. H. published the artcileAssignment of the UV photoelectron spectra of the azoles by ab initio multi-reference configuration interaction calculations, Application of 4H-1,2,4-Triazole, the publication is Chemical Physics (1987), 111(2), 249-61, database is CAplus.

Ab initio multiref. CI calculations were performed on pyrrole, pyrazole, imidazole, each of the triazoles, and tetrazole. The tautomerism of these species is discussed, and the UPS were reinterpreted in the light of the CI data. Many shake-up states were evident ≳14 eV; these can cause difficulties in the positioning of LP_N states by CI methods.

Chemical Physics 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, Application of 4H-1,2,4-Triazole.

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