Category: Triazoles

Sams, Anette Graven published the artcileHit-to-lead optimization of a series of carboxamides of ethyl 2-amino-4-phenylthiazole-5-carboxylates as novel adenosine A_2A receptor antagonists, COA of Formula: C25H29N9O3, the publication is Bioorganic & Medicinal Chemistry Letters (2010), 20(17), 5241-5244, database is CAplus and MEDLINE.

Herein we describe the discovery of a series of novel adenosine A_2A receptor antagonists. A successful hit-to-lead optimization of an HTS hit led to replacement of a metabolically labile ester moiety with a heteroaromatic group. A compound from the series, (cyclopropanecarboxylic acid [5-(5-methyl-[1,2,4]oxadiazol-3-yl)-4-phenyl-thiazol-2-yl]-amide, compound 13), was shown to be effective in reversing haloperidol-induced hypolocomotion, a model of motor dysfunction in Parkinson’s Disease.

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 C25H29N9O3, COA of Formula: C25H29N9O3.

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

Kostikova, L. M. published the artcileEnthalpy characteristics of mononitro derivatives heterocyclic compounds, Computed Properties of 84406-63-3, the publication is International Annual Conference of ICT (2002), 86/1-86/8, database is CAplus.

The enthalpies of formation in the standard condition and gas phase some mononitro derivatives heterocyclic compounds are exptl. determined The cleanliness of some compounds is measured by the method of the curve melting. The substances burnt in the solution of the di-Me phthalate for prevention of explosion and ensuring of completeness of combustion. The thermal effect of reaction of dissolution of substances in the di-Me phthalate is measured on the microcalorimeter and it was taken into account at calculation of the enthalpy of formation of the studied compounds Efficient energies of introduction nitro groups in the heterocycles are found. The change of the enthalpy of formation at introduction of electroneg. fragments to atoms of carbon and nitrogen is analyzed.

International Annual Conference of ICT 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, Computed Properties of 84406-63-3.

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

Ponomareov, O. A. published the artcileNature of electronic transitions in absorption spectra of phenyl derivatives of 1,3,4-sym-triazole, Quality Control of 63598-71-0, the publication is Teoreticheskaya i Eksperimental’naya Khimiya (1993), 29(2), 169-73, database is CAplus.

The absorption spectra of 1,3,4-sym-triazole, its mono-, di-, and tri-Ph derivatives were calculated in π electron approach by PPP CI procedure. Application of the special quantum-chem. excitation indexes allows to classify transitions as being either local or entire mol. in character. The dependence of characteristics on π system structure for the latter case was studied.

Teoreticheskaya i Eksperimental’naya Khimiya 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, Quality Control of 63598-71-0.

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

Ishibashi, Kenji published the artcileOccupancy of adenosine A_2A receptors by istradefylline in patients with Parkinson’s disease using ¹¹C-preladenant PET, Product Details of C25H29N9O3, the publication is Neuropharmacology (2018), 106-112, database is CAplus and MEDLINE.

The present study aimed to calculate occupancy rates of A_2ARs by administrating istradefylline 20 mg or 40 mg, which is the currently approved dose for PD in Japan. Addnl., A_2AR availability was compared between patients with PD and healthy controls. Ten patients with PD under levodopa therapy and six age-matched healthy controls were included. The patients underwent a total of two ¹¹C-preladenant positron emission tomog. scans before and after the administration of istradefylline 20 mg or 40 mg (both n = 5). Binding potential (BP_ND) was calculated to estimate A_2AR availability in the ventral striatum, caudate, and putamen. Maximal A_2AR occupancy and ED₅₀ were estimated by modeling the dose-occupancy curves. All patients were around the middle stage of PD, and their characteristics were clin. heterogeneous. Maximal A_2AR occupancy and ED₅₀ were 93.5% and 28.6 mg in the ventral striatum, 69.5% and 10.8 mg in the caudate, and 66.8% and 14.8 mg in the putamen, resp. There were no significant differences in BP_ND values in the ventral striatum (P = 0.42), caudate (P = 0.72), and putamen (P = 0.43) between the PD and control groups. In conclusion, the present study shows that istradefylline binds to A_2ARs dose-dependently. A sufficient occupancy of A_2ARs could be obtained by administrating the approved dose of istradefylline.

Neuropharmacology 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

Alcami, M. published the artcileEnhanced aluminum(1+) binding energies of some azoles: a theoretical study of azole-X⁺ (X = Na, K, Al) complexes, Computed Properties of 63598-71-0, the publication is Journal of Physical Chemistry (1992), 96(7), 3022-9, database is CAplus.

Hartree-Fock calculations with the 3-21G^* and 6-31G^* basis have been performed to investigate the structure and energetics of Na⁺-, K⁺-, and Al⁺-azole complexes. Structures have been fully optimized at the 3-21G^* level. The structures of azole-Al⁺ complexes resemble closely those of the corresponding protonated species while those of Na⁺ and K⁺ complexes are similar to those found upon Li⁺ association Nevertheless, for Na⁺– and K⁺-bridged structures, when the azolic systems presents two neighbor nitrogens having lone pair electrons, are particularly stable with respect to Li⁺-bridged systems. This implies that Li⁺ vs Na⁺ (or K⁺) binding energies follow two different linear correlations. For these cases where Na⁺ and K⁺ are single coordinated a good linear correlation between their binding energies and the proton affinities is found. A similar behavior is observed when Al⁺ binding energies are considered. The former correlation obeys a quite simple electrostatic model, which is not fulfilled by Al⁺ association energies. Our topol. anal. of the complexes charge d. shows that the Al⁺-azole interaction has a nonnegligible covalent character, which involves the low-lying empty p orbitals of Al⁺. These interactions are responsible for the enhanced stability of some Al⁺ complexes, as for instance, Al⁺-imidazole, which presents a stability very close to that of the Li⁺-imidazole system.

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, Computed Properties of 63598-71-0.

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

Alcami, M. published the artcileA molecular orbital study of azole-lithium(1+) complexes, HPLC of Formula: 63598-71-0, the publication is Journal of Physical Chemistry (1989), 93(10), 3929-36, database is CAplus.

Hartree-Fock calculations with the 6-31G^* basis have been performed to investigate the structure and Li⁺ binding energies of the complexes between Li⁺ and a series of azoles. Structures have been fully optimized at the 3-21G level. A topol. anal. of the Laplacian of the electronic charge d. reveals that the nature of Li⁺-azole complexes is markedly different from that of protonated azoles. In the former, stabilization arises mainly from electrostatic interactions while in the latter a new covalent bond between the basic nitrogen and the incoming proton is actually formed. Basis set superposition error is quite significant, especially for Li⁺-bridging complexes. For those cases where Li⁺ is single coordinated a good linear correlation between Li⁺ binding energies and proton affinities is found, the former being 4 times smaller than the latter. A similar correlation is obtained for the corresponding relative values, although in this case the attenuation factor is only 1.8, as it should be expected from simple ion-dipole interactions. When the azole presents two N atoms having a lone pair of electrons, Li⁺-bridging structures are not always the most stable forms. A discussion on which factors favor this particular conformation is offered.

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

Yanez, Manuel published the artcileCan Conventional Bases and Unsaturated Hydrocarbons Be Converted into Gas-Phase Superacids That Are Stronger than Most of the Known Oxyacids? The Role of Beryllium Bonds, Formula: C2H3N3, the publication is Chemistry – A European Journal (2013), 19(35), 11637-11643, database is CAplus and MEDLINE.

The association of BeX₂ (X: H, F, Cl) derivatives with azoles leads to a dramatic increase of their intrinsic acidity. Hence, whereas 1H-tetrazole can be considered as a typical N base in the gas phase, the complex 1H-tetrazole-BeCl₂ is predicted to be, through the use of high-level G4 ab initio calculations, a nitrogen acid stronger than perchloric acid. This acidity enhancement is due to a more favorable stabilization of the deprotonated species after the beryllium bond is formed, because the deprotonated anion is a much better electron donor than the neutral species. Consequently, this is a general phenomenon that should be observed for any Lewis base, including those in which the basic site is a hydroxy group, an amino group, a carbonyl group, an aromatic N atom, a second-row atom, or the π system of unsaturated hydrocarbons. The consequence is that typical bases like aniline or formamide lead to BeX₂ complexes that are stronger acids than phosphoric or chloric acids. Similarly, water, methanol, and SH₂ become stronger acids than sulfuric acid, pyridine becomes a C acid almost as strong as acetic acid, and unsaturated hydrocarbons such as ethylene and acetylene become acids as strong as nitric and sulfuric acids, resp.

Chemistry – A European Journal 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 C12H10FeO4, Formula: C2H3N3.

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

Vala, Christine published the artcileSynthesis and in vivo Evaluation of Fluorine-18 and Iodine-123 Pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine Derivatives as PET and SPECT Radiotracers for Mapping A_2A Receptors, COA of Formula: C25H29N9O3, the publication is ChemMedChem (2016), 11(17), 1936-1943, database is CAplus and MEDLINE.

Imaging agents that target adenosine type 2A (A_2A) receptors play an important role in evaluating new pharmaceuticals targeting these receptors, such as those currently being developed for the treatment of movement disorders like Parkinson’s disease. They are also useful for monitoring progression and treatment efficacy by providing a noninvasive tool to map changes in A_2A receptor d. and function in neurodegenerative diseases. We previously described the successful evaluation of two A_2A-specific radiotracers in both nonhuman primates and in subsequent human clin. trials: [¹²³I]MNI-420 and [¹⁸F]MNI-444. Herein we describe the development of both of these radiotracers by selection from a series of A_2A ligands, based on the pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine core of preladenant. Each of this series of 16 ligands was found to bind to recombinant human A_2A receptor in the low nanomolar range, and of these 16, six were radiolabeled with either fluorine-18 or iodine-123 and evaluated in nonhuman primates. These initial in vivo results resulted in the identification of 7-(2-(4-(4-(2-[¹⁸F]fluoroethoxy)phenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine ([¹⁸F]MNI-444) and 7-(2-(4-(2-fluoro-4-[¹²³I]iodophenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-imidazo[1,2-c]pyrazolo[4,3-e]pyrimidin-5-amine ([¹²³I]MNI-420) as PET and SPECT radiopharmaceuticals for mapping A_2A receptors in brain.

ChemMedChem 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 C5H10O2S, COA of Formula: C25H29N9O3.

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

Politzer, Peter published the artcileC-NO₂ dissociation energies and surface electrostatic potential maxima in relation to the impact sensitivities of some nitroheterocyclic molecules, Formula: C2H2N4O2, the publication is Molecular Physics (1995), 86(2), 251-5, database is CAplus.

A non-local d. functional procedure (GAUSSIAN 92/DFT, BLYP, 6-13^**) has been used to compute the dissociation energies of the C-NO₂ bond in five unsaturated nitro heterocyclic mols. These show a definite correlation with the maximum of the surface electrostatic potentials above these bonds, which amy explain why these potential maxima are one of the properties that appear in an earlier anal. representation of the measured impact sensitive of nitroheterocyclic compounds

Molecular Physics 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, Formula: C2H2N4O2.

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

Politzer, Peter published the artcileRelationships between dissociation energies and electrostatic potentials of C-NO₂ bonds: applications to impact sensitivities, Related Products of triazoles, the publication is Journal of Molecular Structure (1996), 419-24, database is CAplus.

New data for nitroalkanes support earlier results for nitroheterocycles indicating that C-NO₂ dissociation energies are related to the computed electrostatic potential maxima on the mol. surfaces above these bond regions. This presumably explains the well-established involvement of the electrostatic potential in impact sensitivity correlations; a second factor, for unsaturated systems, is the internal charge separation in the mol.

Journal of Molecular Structure 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, Related Products of triazoles.

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