Category: Triazoles

Wagman, Allan S. published the artcileSynthesis, Binding Mode, and Antihyperglycemic Activity of Potent and Selective (5-Imidazol-2-yl-4-phenylpyrimidin-2-yl)[2-(2-pyridylamino)ethyl]amine Inhibitors of Glycogen Synthase Kinase 3, Application of 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, the main research area is imidazolyl phenylpyrimidinyl pyridylaminoethylamine preparation glycogen synthase kinase inhibitory activity.

In an effort to identify new antidiabetic agents, we have discovered a novel family of (5-imidazol-2-yl-4-phenylpyrimidin-2-yl)[2-(2-pyridylamino)ethyl]amine analogs which are inhibitors of human glycogen synthase kinase 3 (GSK3). We developed efficient synthetic routes to explore a wide variety of substitution patterns and convergently access a diverse array of analogs. Compound I (CHIR-911, CT-99021, or CHIR-73911) emerged from an exploration of heterocycles at the C-5 position, Ph groups at C-4, and a variety of differently substituted linker and aminopyridine moieties attached at the C-2 position. These compounds exhibited GSK3 IC50s in the low nanomolar range and excellent selectivity. They activate glycogen synthase in insulin receptor-expressing CHO-IR cells and primary rat hepatocytes. Evaluation of lead compounds I and II (CHIR-611 or CT-98014) in rodent models of type 2 diabetes revealed that single oral doses lowered hyperglycemia within 60 min, enhanced insulin-stimulated glucose transport, and improved glucose disposal without increasing insulin levels.

Journal of Medicinal Chemistry published new progress about Antidiabetic agents. 24415-66-5 belongs to class triazoles, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, and the molecular formula is C6H5ClN4, Application of 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Iwamura, Ryo published the artcileIdentification of a Selective, Non-Prostanoid EP2 Receptor Agonist for the Treatment of Glaucoma: Omidenepag and its Prodrug Omidenepag Isopropyl, SDS of cas: 143426-50-0, the main research area is prostanoid EP2 receptor agonist preparation glaucoma.

EP2 receptor agonists are expected to be effective ocular hypotensive agents; however, it has been suggested that agonism to other EP receptor subtypes may lead to undesirable effects. Through medicinal chem. efforts, we identified a scaffold bearing a (pyridin-2-ylamino)acetic acid moiety as a promising EP2-selective receptor agonist. (6-((4-(Pyrazol-1-yl)benzyl)(pyridin-3-ylsulfonyl)aminomethyl)pyridin-2-ylamino)acetic acid 13ax (omidenepag, OMD) exerted potent and selective activity toward the human EP2 receptor (h-EP2). Low doses of omidenepag iso-Pr (OMDI), a prodrug of 13ax, lowered intraocular pressure (IOP) in ocular normotensive monkeys. OMDI was selected as a clin. candidate for the treatment of glaucoma.

Journal of Medicinal Chemistry published new progress about Antiglaucoma agents. 143426-50-0 belongs to class triazoles, name is 4-(1,2,4-Triazol-1-yl)benzyl Alcohol, and the molecular formula is C9H9N3O, SDS of cas: 143426-50-0.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Werbel, Leslie M. published the artcilePotential antimalarial substances. XIV. [[(Dialkylamino)alkyl]amino]pyrimido[1,2-a]benzimidazoles, 2,3,-dihydro-1H-cyclopenta[4,5]pyrimido[1,2-a]benzimidazoles, and s-triazolo[1,5-a]pyrimidines as potential antimalarial agents, Synthetic Route of 24415-66-5, the main research area is pyrimido benzimidazoles; benzimidazoles pyrimido; cyclopentapyrimidobenzimidazoles; triazolo pyrimidines; pyrimidines triazolo.

The structure of the product of the reaction of 2-aminobenzimidazole with ethyl acetoacetate was established by NMR spectroscopy as 2-methylpyr imido[1,2-a]benzimidazol-4-ol (I). 7(and 8)-Chloro-2-methylpyrimido[1,2-a]benzimidazol-4-ol (II and III), 2-(trifluoromethyl)pyrimido[1,2-a]benzimidazol-4-ol, 2,7,8-trimethylpyrimido[1,2-a]benzimidazol-4-ol, 2-benzyl-1,2,3,4-tetrahydropyrido-[4′,3′:4,5]pyrimido[1,2-a]benzimidazol-12-ol, 1,2,3,4-tetrahydro-benzimidazo[2,1-b]quinazolin-12-ol, and 2,3-dihydro-1H-cyclopenta[4,5]pyrimido[1,2-a]benzimidazol-11-ol (IV) were prepared in a similar manner. Chlorination of I, II, III, IV, and 5-methyl-s-triazolo[1,5-a]pyrimidin-7-ol with POCl3 afforded the corresponding chloroheterocycles, which were condensed with the appropriate N,N-dialkylalkylenediamine or Na,Na-diethyl-6-methoxytoluene-α,3-diamine to give various 4-[[(dialkylamino)-alkyl]amino]-2-methylpyrimido[1,2-a]benzimidazoles, 11-[[(dialkylamino)alkyl]amino]-2,3-dihydro-1H-cyclopenta[4,5]pyrimido[1,2-a] benzimidazoles and 7-[[(dialkylamino)alkyl]-amino]-5-methyl-s-triazolo[1,5-a]pyrimidines. None of these compounds displayed significant antimalarial activity against Plasmodium berghei in the mouse.

Journal of Heterocyclic Chemistry published new progress about Drugs. 24415-66-5 belongs to class triazoles, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, and the molecular formula is C6H5ClN4, Synthetic Route of 24415-66-5.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Gomez, Laurent published the artcileDesign and Synthesis of Novel and Selective Phosphodiesterase 2 (PDE2a) Inhibitors for the Treatment of Memory Disorders, Synthetic Route of 24415-66-5, the main research area is triazolopyrimidine preparation PDE2a inhibitor SAR memory disorder treatment.

A series of potent and selective [1,2,4]triazolo[1,5-a]pyrimidine PDE2a inhibitors is reported. The design and improvement of the binding properties of this series was achieved using X-ray crystal structures in conjunction with careful anal. of electronic and structural requirements for the PDE2a enzyme. One of the lead compounds, compound I (DNS-8254), was identified as a potent and highly selective PDE2a enzyme inhibitor with favorable rat pharmacokinetic properties. Interestingly, the increased potency of compound I was facilitated by the formation of a halogen bond with the oxygen of Tyr827 present in the PDE2a active site. In vivo, compound I demonstrated significant memory enhancing effects in a rat model of novel object recognition. Taken together, these data suggest that compound I may be a useful tool to explore the pharmacol. of selective PDE2a inhibition.

Journal of Medicinal Chemistry published new progress about Memory disorders. 24415-66-5 belongs to class triazoles, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, and the molecular formula is C6H5ClN4, Synthetic Route of 24415-66-5.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Umar, Tarana published the artcileA multifunctional therapeutic approach: Synthesis, biological evaluation, crystal structure and molecular docking of diversified 1H-pyrazolo[3,4-b]pyridine derivatives against Alzheimer’s disease, Application of 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, the main research area is piperazinyl pyrazolopyridinyl acetamide preparation docking cholinesterase inhibitor amyloid aggregation; AChE inhibitors; Amyloid β aggregation inhibitors; Docking; N-(1H-pyrazolo[3,4-b]pyridin-3-yl)acetamides; Selectivity.

2-(Piperazin-1-yl)-N-(1H-pyrazolo[3,4-b]pyridin-3-yl)acetamides I [R = piperidin-1-yl, 4-methylpiperazin-1-yl, Et 4-((4-yl)piperazin-1-yl)quinoline-3-carboxylate, etc.] were described as a new class of selective and potent acetylcholinesterase (AChE) inhibitors and amyloid β aggregation inhibitors. Formation of synthesized compounds I was justified via 1H NMR, 13C NMR, mass spectra and single crystal X-Ray diffraction study. All compounds were evaluated for their acetylcholinesterase and butyrylcholinesterase inhibitory activity, inhibition of self-mediated Aβ aggregation and Cu(II)-mediated Aβ aggregation. Also, docking study was carried out in concordance with in vitro results. The most potent mol. amongst the derivatives exhibited excellent anti-AChE activity (IC50 = 4.8 nM). Kinetic study of I [R = 2-((4-yl)piperazin-1-yl)-N-(1H-pyrazolo[3,4-b]pyridin-3-yl)acetamide] suggested it to be a mixed type inhibitor. In vitro study revealed that all the compounds were capable of inhibiting self-induced β-amyloid (Aβ) aggregation with the highest inhibition percentage to be 81.65%. Potency of I [R = Et 4-((4-yl)piperazin-1-yl)quinoline-3-carboxylate, 2-((4-yl)piperazin-1-yl)-N-(1H-pyrazolo[3,4-b]pyridin-3-yl)acetamide] to inhibit self-induced Aβ1-42 aggregation was ascertained by TEM anal. Compounds were also evaluated for their Aβ disaggregation, antioxidation, metal-chelation activity.

European Journal of Medicinal Chemistry published new progress about Aggregation. 24415-66-5 belongs to class triazoles, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, and the molecular formula is C6H5ClN4, Application of 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Yuan, Shuo published the artcileBronsted Acid-Catalyzed Direct C(sp2)-H Heteroarylation Enabling the Synthesis of Structurally diverse Biaryl Derivatives, Related Products of triazoles, the main research area is chloro heteroarene arene hexafluoroisopropanol catalyst arylation; heterocyclic biaryl preparation.

Bronsted acid-catalyzed direct C(sp2)-H heteroarylation that enabled the synthesis of biaryl fragments in moderate to excellent yields (up to 99% yield), which was also performed at a gram scale and successfully applied to the privileged quinazoline scaffolds of the first-generation epidermal growth factor receptor (EGFR) inhibitors Gefitinib and Erlotinib, offering rapid access to a series of quinazoline-based biaryl compounds Addnl., the late-stage diversifications were performed based on the compound 5-methyl-7-(2,4,6-trimethoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, generating a library of structurally diverse and complex biaryl compounds

Advanced Synthesis & Catalysis published new progress about Arylation. 24415-66-5 belongs to class triazoles, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, and the molecular formula is C6H5ClN4, Related Products of triazoles.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Yin, Weiyu published the artcileHighly Practical Synthesis of Nitriles and Heterocycles from Alcohols under Mild Conditions by Aerobic Double Dehydrogenative Catalysis, HPLC of Formula: 143426-50-0, the main research area is alc aerobic double dehydrogenation ammonia nitrile synthesis; biaryl heterocycle one pot synthesis nitrile in situ heterocyclization.

A mild, aerobic, catalytic process for obtaining nitriles directly from alcs. and aqueous ammonia is described (RC6H4CH2OH + NH3 → RC6H4CN). The reaction proceeds via a dehydrogenation cascade mediated by catalytic CuI, bpy, and TEMPO in the presence of O2. The substrate scope is broad including various functionalized aromatic and aliphatic alcs. This protocol enabled the one-pot synthesis of various biaryl heterocycles directly from com. available alcs. (e.g., PhCH2OH + NH3 in first step; addition of ethylenediamine in second step → 2-phenyl-4,5-dihydro-1H-imidazole).

Organic Letters published new progress about Aliphatic alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 143426-50-0 belongs to class triazoles, name is 4-(1,2,4-Triazol-1-yl)benzyl Alcohol, and the molecular formula is C9H9N3O, HPLC of Formula: 143426-50-0.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Temple, Kayla J. published the artcileDiscovery of a novel 2,3-dimethylimidazo[1,2-a]pyrazine-6-carboxamide M4 positive allosteric modulator (PAM) chemotype, Product Details of C7H6BrN3, the main research area is dimethylimidazopyrazinecarboxamide preparation M4 pos allosteric modulator; M(4); Muscarinic acetylcholine receptor; Positive allosteric modulator (PAM); Structure activity relationship (SAR).

This Letter details the authors’ efforts to discover structurally unique M4 PAMs containing 5,6-heteroaryl ring systems. In an attempt to improve the DMPK profiles of the 2,3-dimethyl-2H-indazole-5-carboxamide and 1-methyl-1H-benzo[d][1,2,3]triazole-6-carboxamide cores, the authors studied a plethora of core replacements. This exercise identified a novel 2,3-dimethylimidazo[1,2-a]pyrazine-6-carboxamide core that provided improved M4 PAM activity and CNS penetration.

Bioorganic & Medicinal Chemistry Letters published new progress about Molecular structure-property relationship. 108281-78-3 belongs to class triazoles, name is 6-Bromo-3-methyl-[1,2,4]triazolo[4,3-a]pyridine, and the molecular formula is C7H6BrN3, Product Details of C7H6BrN3.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Nugent, Jeremy published the artcileA General Route to Bicyclo[1.1.1]pentanes through Photoredox Catalysis, Application In Synthesis of 143426-50-0, the main research area is bicyclopentane preparation photoredox catalyst halide carbocyclepropellane addition.

Photoredox catalysis has transformed the landscape of radical-based synthetic chem. Additions of radicals generated through photoredox catalysis to carbon-carbon π-bonds are well-established; however, this approach has yet to be applied to the functionalization of carbon-carbon σ-bonds. Here, the authors report the first such use of photoredox catalysis to promote the addition of organic halides to the carbocycle [1.1.1]propellane; the product bicyclo[1.1.1]pentanes (BCPs) are motifs of high importance in the pharmaceutical industry and in materials chem. Showing broad substrate scope and functional group tolerance, this methodol. results in the first examples of bicyclopentylation of sp2 carbon-halogen bonds to access (hetero)arylated BCPs, as well as the functionalization of nonstabilized sp3 radicals. Substrates containing alkene acceptors allow the single-step construction of polycyclic bicyclopentane products through unprecedented atom transfer radical cyclization cascades, while the potential to accelerate drug discovery is demonstrated through late-stage bicyclopentylations of natural product-like and drug-like mols. Mechanistic studies demonstrate the importance of the photocatalyst in this chem. and provide insight into the balance of radical stability and strain relief in the reaction cycle.

ACS Catalysis published new progress about Photocatalysts. 143426-50-0 belongs to class triazoles, name is 4-(1,2,4-Triazol-1-yl)benzyl Alcohol, and the molecular formula is C9H9N3O, Application In Synthesis of 143426-50-0.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Loubidi, Mohammed published the artcilePd-catalyzed Suzuki/Sonogashira cross-coupling reaction and the direct sp3 arylation of 7-chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, Application of 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, the main research area is methyltriazolopyrimidine chloro preparation aryl alkyne palladium catalyst Sonogashira coupling; arylalkynyl methyltriazolopyrimidine preparation; chloro methyltriazolopyrimidine preparation arylboronic acid palladium catalyst Suzuki coupling; aryl methyltriazolopyrimidine preparation bromobenzene palladium catalyst arylation; benzyl aryl methyltriazolopyrimidine preparation.

A rapid and efficient method was reported for the synthesis of the [1,2,4]triazolo[1,5-a]pyrimidine motif. Palladium catalyzed Suzuki and Sonogashira cross coupling reactions on 7-chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine were performed. The direct sp3 arylation of compounds resulting from the Suzuki reaction was then carried out.

Tetrahedron Letters published new progress about Arylation. 24415-66-5 belongs to class triazoles, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, and the molecular formula is C6H5ClN4, Application of 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics