Category: Triazoles

Sekioka, Ryuichi published the artcileDiscovery of N-ethylpyridine-2-carboxamide derivatives as a novel scaffold for orally active γ-secretase modulators, Name: 4-(1,2,4-Triazol-1-yl)benzyl Alcohol, the main research area is Alzheimer’s disease gamma secretase modulator myloid beta peptide; Alzheimer’s disease; Amyloid-beta peptide; Cytochrome P450 3A4; Gamma-secretase modulator.

Gamma-secretase modulators (GSMs) are promising disease-modifying drugs for Alzheimer’s disease because they can selectively decrease pathogenic amyloid-β42 (Aβ42) levels. Here we report the discovery of orally active N-ethylpyridine-2-carboxamide derivatives as GSMs. The isoindolinone moiety of 5-[8-(benzyloxy)-2-methylimidazo[1,2-a]pyridin-3-yl]-2-ethyl-2,3-dihydro-1H-isoindol-1-one hydrogen chloride (1a) was replaced with a picolinamide moiety. Optimization of the benzyl group significantly improved GSM activity and mouse microsomal stability. 5-{8-[([1,1′-Biphenyl]-4-yl)methoxy]-2-methylimidazo[1,2-a]pyridin-3-yl}-N-ethylpyridine-2-carboxamide hydrogen chloride (1v) potently reduced Aβ42 levels with an IC50 value of 0.091μM in cultured cells without inhibiting CYP3A4. Moreover, 1v demonstrated a sustained pharmacokinetic profile and significantly reduced brain Aβ42 levels in mice.

Bioorganic & Medicinal Chemistry published new progress about Alzheimer disease. 143426-50-0 belongs to class triazoles, name is 4-(1,2,4-Triazol-1-yl)benzyl Alcohol, and the molecular formula is C9H9N3O, Name: 4-(1,2,4-Triazol-1-yl)benzyl Alcohol.

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

Wang, Ruihu published the artcileHeterocyclic-Based Nitrodicyanomethanide and Dinitrocyanomethanide Salts: A Family of New Energetic Ionic Liquids, Category: triazoles, the main research area is nitrodicyanomethanide dinitrocyanomethanide salt energetic ionic liquid crystallog.

Twelve novel energetic salts 1a-f and 2a-f with nitrodicyanomethanide and dinitrocyanomethanide anions paired with 1,5-diamino-4-methyltetrazolium, 1,4-dimethyl-5-aminotetrazolium 1,4,5-trimethyltetrazolium, 1-methyl-4-amino-1,2,4-triazolium, 1,4-dimethyltriazolium, and 1,3-dimethylimidazolium were prepared through metathesis reactions of equivalent silver(I) salts with corresponding iodide salts in acetonitrile. Key phys. properties, such as m.p., thermal stability and d., were measured. The relation between their structures and these properties was determined The structures of 1,5-diamino-4-methyltetrazolium-based salts 1a and 2a were further confirmed by single-crystal X-ray anal. The densities and standard enthalpies of formation for these energetic salts were calculated All of the salts possess higher enthalpies of formation than the nitrate analogs.

Inorganic Chemistry published new progress about Crystal structure. 39602-93-2 belongs to class triazoles, name is 4-Amino-1-methyl-4H-1,2,4-triazol-1-ium iodide, and the molecular formula is C3H7IN4, Category: triazoles.

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

Belletire, John L. published the artcilePairing heterocyclic cations with closo-dodecafluorododecaborate (2-), Application of 4-Amino-1-methyl-4H-1,2,4-triazol-1-ium iodide, the main research area is pairing heterocyclic cation closo dodecafluorododecaborate; dipotassium closo dodecafluorododecaborate reaction heterocyclium salt; crystal mol structure triazolium imidazolium pyrimidinium purinium closo dodecafluorododecaborate.

Eight binary salts that pair triazolium(1+), imidazolium(1+), pyrimidinium(1+), or purinium(1+) cations with the icosahedral closo-dodecafluorododecaborate(2-) anion (B12F12 2-) were synthesized using open-air benchtop metathesis reactions in water or acetonitrile. The scale of the reactions varied from just milligrams to nearly one gram of the K2B12F12 starting material. Other reaction conditions, the scope of the reaction, and the solubilities for the new salts are discussed. Five [heterocyclium]2[B12F12] salts, which were obtained in yields ranging from 84% to 99%, displayed significantly higher densities than the corresponding previously reported analogous [heterocyclium]2[B12H12] and [heterocyclium][CB11H12] salts. A ninth high-d. salt consisted of B12F12 2- paired with a complex Ag4(triazole)8 4+ cation. The structures of eight of the nine new compounds were determined by single-crystal x-ray diffraction anal. The d. of five [heterocyclium]2[B12F12] salts was found to increase approx. linearly as the distance between the five-membered-ring heterocyclium(1+) cation centroids decreased. This work demonstrates addnl. flexibility for the rational design of ionic structures with predictable properties, which will ultimately permit the tailoring of ingredient-response behavior.

Journal of Fluorine Chemistry published new progress about Crystal structure. 39602-93-2 belongs to class triazoles, name is 4-Amino-1-methyl-4H-1,2,4-triazol-1-ium iodide, and the molecular formula is C3H7IN4, Application of 4-Amino-1-methyl-4H-1,2,4-triazol-1-ium iodide.

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

Xue, Hong published the artcileEnergetic salts of substituted 1,2,4-triazolium and tetrazolium 3,5-dinitro-1,2,4-triazolates, HPLC of Formula: 39602-93-2, the main research area is energetic salt triazolium tetrazolium dinitrotriazolate.

Energetic salts comprised of substituted 1,2,4-triazolium and tetrazolium cations and 3,5-dinitro-1,2,4-triazolate anion were synthesized and characterized. The structure of 4,5-dimethyl-1-aminotetrazolium 3,5-dinitro-1,2,4-triazolate (16) was confirmed by X-ray anal. Based on exptl. obtained heats of combustion, these materials have calculated heats of formation ranging from ΔHf° = 118 (2) to 778 kJ mol-1 (10) with densities >1.5 g cm-3. Salts, 2, 4, 7, 9 and 10, fall into the ionic liquid class (mp < 100 °C). Journal of Materials Chemistry published new progress about Crystal structure. 39602-93-2 belongs to class triazoles, name is 4-Amino-1-methyl-4H-1,2,4-triazol-1-ium iodide, and the molecular formula is C3H7IN4, HPLC of Formula: 39602-93-2.

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

Wang, Kangcai published the artcileIodocuprate-containing ionic liquids as promoters for green propulsion, Product Details of C3H7IN4, the main research area is iodocuprate ionic liquid promoter propulsion boron containing fuel.

In this work, four novel iodocuprate-containing ionic liquids, CuILs are prepared and comprehensively characterized. In addition to their interesting mol. structures and phys. properties CuILs exhibited capability to efficiently promote hypergolic reactions between boron-containing [EMIM+][H3BCN-] and [MIM]·[BH3] fuels and a highly concentrated H2O2 (95%) oxidizer. The most promising promoter CuIL 3 has the decomposition temperature well above the decomposition temperature of the fuels, was stable in promoter-in-fuel mixtures for weeks and showed ignition delay times down to 14 ms. It is believed that further development of the new iodocuprate ionic liquids can lead to promising “”green”” H2O2-based bipropellant systems for space applications.

Journal of Materials Chemistry A: Materials for Energy and Sustainability published new progress about Crystal structure. 39602-93-2 belongs to class triazoles, name is 4-Amino-1-methyl-4H-1,2,4-triazol-1-ium iodide, and the molecular formula is C3H7IN4, Product Details of C3H7IN4.

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

Wang, Shuai published the artcileDiscovery of new [1,2,4] Triazolo[1,5-a]Pyrimidine derivatives that Kill gastric cancer cells via the mitochondria pathway, Synthetic Route of 24415-66-5, the main research area is triazolopyrimidinylamino diarylpropenone preparation antitumor activity SAR; 1,2,4]triazolo[1,5-a]pyrimidines; Apoptosis; Autophagy; Gastric cancer; Mitochondrial pathway.

A novel series of [1,2,4]triazolo[1,5-a]pyrimidine-based compoundsI [R1 = benzyl, 4-fluorobenzyl, 4-chlorobenzyl, etc.; R2 = Me, Et, Ph; R3 = H, Me] and II [R4 = Ph, (4-(3-(6-bromo-2-pyridyl)prop-2-enoyl)phenyl), (4-(3-(5-bromo-2-pyridyl)prop-2-enoyl)phenyl), etc.] were synthesized and tested their anti-proliferation efficacy against gastric cancer cell line MGC-803. Among them, compounds II [R4 = (4-(3-(6-bromo-2-pyridyl)prop-2-enoyl)phenyl), (4-(3-(5-bromo-2-pyridyl)prop-2-enoyl)phenyl)] inhibited gastric cancer cells at micromolar level. Compound II [R4 = (4-(3-(6-bromo-2-pyridyl)prop-2-enoyl)phenyl)] caused G2/M arrest and induced mitochondria-dependent apoptosis in MGC-803 and SGC-7901. However, inhibiting apoptosis pathway cannot prevent the inhibitory activity of compound II [R4 = (4-(3-(6-bromo-2-pyridyl)prop-2-enoyl)phenyl)] against gastric cancer cell. To our surprising, ROS level was increased by compound II [R4 = (4-(3-(6-bromo-2-pyridyl)prop-2-enoyl)phenyl)] and elevation of ROS could be rescued by NAC. In accordance with that, NAC absolutely prevented the anti-proliferation efficacy of compound 4o. We further found that autophagy inhibitor CQ rather than 3-MA partially reversed inhibitory activity of compound II [R4 = (4-(3-(6-bromo-2-pyridyl)prop-2-enoyl)phenyl)] in MGC-803 cells. Taken together, compound II [R4 = (4-(3-(6-bromo-2-pyridyl)prop-2-enoyl)phenyl)] exhibited its anti-proliferative activity via increasing ROS level and inducing autophagy, thus leading to apoptosis of gastric cancer cells. Therefore, compound II [R4 = (4-(3-(6-bromo-2-pyridyl)prop-2-enoyl)phenyl)] may support further development of lead compounds for gastric cancer therapy via mitochondria pathway.

European Journal of Medicinal Chemistry published new progress about Antitumor 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, Synthetic Route of 24415-66-5.

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

Wang, Shuai published the artcileSynthesis, structure-activity relationship studies and biological characterization of new [1,2,4]triazolo[1,5-a]pyrimidine-based LSD1/KDM1A inhibitors, SDS of cas: 24415-66-5, the main research area is triazolopyrimidine preparation SAR LSD1 KDM1A inhibitor anticancer activity; Antiproliferative activity; LSD1 inhibitors; Migration inhibition; [1,2,4]triazolo[1,5-a]pyrimidines.

The design, synthesis and biochem. characterization of [1,2,4]triazolo[1,5-a]pyrimidine derivatives I [R1 = H, [(2-bromophenyl)methyl]sulfanyl, prop-2-en-1-ylsulfanyl, [(1H-1,3-benzodiazol-2-ylmethyl)sulfanyl], etc.; R2 = H, Me, (CH2)4CH3; R3 = Me, Et, C6H5; R2, R3 = -(CH2)3-; R4 = H, C6H5, [4-(4-methylpiperazin-1-yl)phenyl], etc.] as new LSD1 inhibitors have been reported. Of these compounds, compound I [R1 = (1H-1,3-benzodiazol-2-ylsulfanyl)methyl; R2 = H; R3 = Me; R4 = [4-(4-methylpiperazin-1-yl)phenyl]] (II) inhibited LSD1 in a reversible manner (IC50 = 1.72 μM) and showed selectivity to LSD1 over MAO-A/B. Besides, compound II displayed FAD-competitive binding to LSD1. Interestingly, compound II did not inhibit horseradish peroxidase (HRP) and quench H2O2, thus excluding the possibility that LSD1 inhibition by compound II was due to the HRP inhibition and consumption of H2O2. In LSD1 overexpressed A549 cells, compound II concentration-dependently induced accumulation of H3K4me1/me2 and H3K9me2 and showed cellular target engagement to LSD1. Addnl., compound II significantly inhibited migration of A549 cells in a concentration-dependent manner, further western blot anal. showed that compound II increased expression levels of epithelial cell markers E-Cadherin and Claudin-1, down-regulated mesenchymal cell marker N-Cadherin and the upstream transcription factors Snail and Slug. Docking studies were also performed to rationalize the potency of compound II toward LSD1. To conclude, the [1,2,4]triazolo[1,5-a]pyrimidine I could serve as a promising scaffold for the development of new LSD1 inhibitors.

European Journal of Medicinal Chemistry published new progress about Antitumor 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, SDS of cas: 24415-66-5.

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

Wang, Shuai published the artcileDevelopment of Highly Potent, Selective, and Cellular Active Triazolo[1,5-a]pyrimidine-Based Inhibitors Targeting the DCN1-UBC12 Protein-Protein Interaction, Synthetic Route of 24415-66-5, the main research area is triazolo pyrimidine derivative preparation DCN1 UBC12 protein interaction cancer.

The cullin-RING ubiquitin ligases (CRLs) are responsible for about 20% of cellular protein degradation and regulate diverse cellular processes, and the dysfunction of CRLs is implicated in human diseases. Targeting the CRLs has become an emerging strategy for the treatment of human diseases. Herein, we describe the discovery of a hit compound from our inhouse library and further structure-based optimizations, which have enabled the identification of new triazolo[1,5-a]pyrimidine-based inhibitors targeting the DCN1-UBC12 interaction. Compound WS-383 blocks the DCN1-UBC12 interaction (IC50 = 11 nM) reversibly and shows selectivity over selected kinases. WS-383 exhibits cellular target engagement to DCN1 in MGC-803 cells. WS-383 inhibits Cul3/1 neddylation selectively over other cullins and also induces accumulation of p21, p27, and NRF2. Collectively, targeting the DCN1-UBC12 interaction would be a viable strategy for selective neddylation inhibition of Cul3/1 and may be of therapeutic potential for disease treatment in which Cul3/1 is dysregulated.

Journal of Medicinal Chemistry published new progress about Antitumor 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, Synthetic Route of 24415-66-5.

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

Sanchez, Robert M. published the artcileSynthesis and structure-activity relationships of 1,2,4-triazolo[1,5-a]pyrimidin-7(3H)-ones as novel series of potent β isoform selective phosphatidylinositol 3-kinase inhibitors, Application In Synthesis of 502546-41-0, the main research area is triazolo pyrimidinone preparation phosphatidylinositol 3 kinase inhibitor anticancer SAR.

A series of 1,2,4-triazolo[1,5-a]pyrimidin-7(3H)-ones with excellent enzyme inhibition, improved isoform selectivity, and excellent inhibition of downstream phosphorylation of AKT has been identified. Several compounds in the series demonstrated potent (∼ 0.100 μM IC50) growth inhibition in a PTEN deficient cancer cell line.

Bioorganic & Medicinal Chemistry Letters published new progress about Antitumor agents. 502546-41-0 belongs to class triazoles, name is 5-Cyclopropyl-4H-1,2,4-triazol-3-amine, and the molecular formula is C5H8N4, Application In Synthesis of 502546-41-0.

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

Li, Zhong-Rui published the artcileExperience-based discovery (EBD) of aryl hydrazines as new scaffolds for the development of LSD1/KDM1A inhibitors, Category: triazoles, the main research area is LSD1 inhibitor experience discovery aryl hydrazine scaffolds; Aryl hydrazines; Epigenetic regulation; Experience-based discovery; LSD1 inhibitors; [1, 2, 4] triazolo[1, 5- a] pyrimidine.

Phenelzine was first employed to design new aryl hydrazine-based LSD1 inhibitors based on the experience-based discovery (EBD) strategy. Among these compounds, D8 potently inhibited LSD1 (IC50 = 882.30 nM) in a reversible manner. Compound D8 was selective to LSD1 over MAO-A/B and showed H3K4me2 competitive binding to LSD1. The interaction between H3K4me2 and LSD1 was also confirmed by the Co-IP assay. In LSD1 overexpressed A549 cells, compound D8 dose-dependently induced accumulation of LSD1 substrates H3K4me1/2 and H3K9me1/2, showed cellular target engagement to LSD1 and significantly inhibited cell migration of A549 cells. Docking studies suggested that compound D8 occupied the peptide binding region and therefore blocked the access of the peptide substrate to the FAD, finally leading to the demethylase activity inhibition of LSD1. The findings indicate that aryl hydrazines are new scaffolds for the design of LSD1 inhibitors, the identification of D8 provides further evidence for our previously proposed general principle that fused heterocycles with an amine group are potentially active toward LSD1 by competitive binding to LSD1 with H3 peptide substrates.

European Journal of Medicinal Chemistry published new progress about Antitumor 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, Category: triazoles.

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