Category: Triazoles

Artico, M. published the artcileAromatic hydrazides as specific inhibitors of bovine serum amine oxidase, Quality Control of 143426-50-0, the main research area is aromatic hydrazide preparation amine oxidase inhibitor; structure activity hydrazide oxidase inhibitor.

New hydrazides were synthesized in search for specific inhibitors of bovine serum amine oxidase: a series of benzoic and phenylacetic acid hydrazides containing the 1H-imidazol-1-yl or the 1H-imidazol-1-ylmethyl group as as o-, m-, or p-substituent in the Ph ring; an analogous series of p-substituted phenylhydrazides with a 5 or 6-membered heterocyclic ring substituent, and a series of similar phenylpropionic hydrazides. The longer and more flexible phenylacetic hydrazides, and to a somewhat lesser extent the phenylpropionic ones, were better specific inhibitors of bovine serum amine oxidase than the benzoic hydrazides, which were also bound by the enzyme with high affinity, but at a slow rate. Derivatives with p- and m-substituents were more reactive than the o-substituted ones. The chem. nature of the substituent was less important than its position in the Ph ring and the presence of methylene spacers. These data point to the presence of a hydrophobic site at short distance from the protein carbonyl cofactor, so that simultaneous interaction of the 2 ends of the inhibitor mol. can occur at the 2 sites. The presence of the hydrophobic site was confirmed by the capability of some mols. deprived of the hydrazidic group to act as mild inhibitors. All hydrazides were less reactive by 2-3 orders of magnitude towards pig kidney diamine oxidase and FAD-dependent monoamine oxidase from rat brain mitochondria, while the other compounds showed similar inhibition power against all proteins. The specificity for the bovine enzyme seems therefore to be related to the concerted action of the 2 moieties of the inhibitor mol.

European Journal of Medicinal Chemistry published new progress about aromatic hydrazide preparation amine oxidase inhibitor; structure activity hydrazide oxidase inhibitor. 143426-50-0 belongs to class triazoles, name is 4-(1,2,4-Triazol-1-yl)benzyl Alcohol, and the molecular formula is C9H9N3O, Quality Control of 143426-50-0.

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

Moran, Daniel B. published the artcileSynthesis of (pyridinyl)-1,2,4-triazolo[4,3-a]pyridines, Recommanded Product: 6-Bromo-3-methyl-[1,2,4]triazolo[4,3-a]pyridine, the main research area is pyridinylpyridinone chlorination; chloropyridine condensation hydrazine; hydrazinopyridine orthoformate cyclization; triazolopyridine pyridinyl.

The principal route for the synthesis of pyridinyltriazolopyridines I (R = H, Me) was based upon the intermediate 2-chloropyridines II (R1 = Cl), which were prepared by the chlorination of pyridinylpyridinones. Direct chlorination of N-oxides III with POCl3 gave chloro-substituted mixtures, whereas rearrangement of III with Ac2O followed by chlorination gave exclusively II (R1 = Cl). Condensation of II with N2H4 gave II(R1 = NHNH2), which were cyclized with RC(OEt)3 to give I.

Journal of Heterocyclic Chemistry published new progress about pyridinylpyridinone chlorination; chloropyridine condensation hydrazine; hydrazinopyridine orthoformate cyclization; triazolopyridine pyridinyl. 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, Recommanded Product: 6-Bromo-3-methyl-[1,2,4]triazolo[4,3-a]pyridine.

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

Kawaguchi, Mitsuyasu published the artcileDevelopment of an ENPP1 Fluorescence Probe for Inhibitor Screening, Cellular Imaging, and Prognostic Assessment of Malignant Breast Cancer, Name: 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, the main research area is ENPP1 fluorescence probe inhibitor screening imaging prognostic breast cancer.

Ectonucleotide pyrophosphatase/phosphodiesterase 1 (ENPP1) is a type II transmembrane glycoprotein that is involved in bone metabolism and insulin resistance, hydrolyzes 2′,3′-cGAMP (a STING ligand that promotes innate immunity), and is associated with cancer stemness in breast cancers and glioblastoma. Therefore, ENPP1 is considered a candidate therapeutic target and/or biomarker for early diagnosis of malignant tumors. In this study, we designed and synthesized a sensitive ENPP1 fluorescence probe, Tokyo Green (TG) mAMP. We used it to screen a chem. library for non-phosphate ENPP1 inhibitors. Structural optimization of a selected hit afforded a potent and specific ENPP1 inhibitor. We further found that ENPP1 mRNA expression in tissue samples from patients with triple-neg. breast cancer was significantly inversely related to recurrence-free survival (RFS) and overall survival (OS), and TG-mAMP assay revealed a significant difference in ENPP1 activity between ENPP1 high-expressing and ENPP1 low-expressing samples. Our results suggest that TG-mAMP assay might be a rapid and inexpensive tool for predicting the prognosis of patients with malignant breast cancers.

Journal of Medicinal Chemistry published new progress about Cancer diagnosis. 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, Name: 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine.

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

Savateev, Aleksandr published the artcileHalogen free 1,2,3- and 1,2,4-triazolide based ionic liquids: synthesis and properties, Category: triazoles, the main research area is azolium triazolide ionic liquid preparation thermal stability dynamic viscosity.

Triazoles were successfully used as building blocks to create “”fully organic”” ILs featuring on both sides organic ions, i.e., 1,2,3- or 1,2,4-triazolide anions and 1,2,4-triazolium or imidazolium cations. Glass transition temperatures, densities and viscosities of these ILs were determined Their electrochem. and thermal stability and also conductivity, were higher than those for known ILs.

Chemical Communications (Cambridge, United Kingdom) published new progress about Current density. 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

Moderhack, Dietrich published the artcilePhenylcarbamoylation of N-acetyl-1,2,4-triazolium-4-aminides revisited, Recommanded Product: 4-Amino-1-methyl-4H-1,2,4-triazol-1-ium iodide, the main research area is phenylcarbamoylation acetyltriazolium aminide.

The reaction of N-acetyl-1,2,4-triazolium-4-aminides with PhSCN affords ring functionalized products rather than linear adducts. Analogous compounds are obtained from 1-acetamido-4-methyl-4H-1,2,4-triazolium iodide and its imidazolium congener. Twofold carbamoylation occurs on reaction of aminotriazolium salts in the presence of base. Azoliums having Me at C(5)/(2) are inert throughout.

Heterocycles published new progress about Carbamoylation. 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, Recommanded Product: 4-Amino-1-methyl-4H-1,2,4-triazol-1-ium iodide.

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

Phillips, Margaret A. published the artcileTriazolopyrimidine-Based Dihydroorotate Dehydrogenase Inhibitors with Potent and Selective Activity against the Malaria Parasite Plasmodium falciparum, Recommanded Product: 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, the main research area is triazolopyrimidine preparation crystal structure dihydroorotate dehydrogenase inhibitor antimalarial agent; triazolo pyrimidine preparation dihydroorotate dehydrogenase inhibitor antimalarial Plasmodium falciparum.

A Plasmodium falciparum dihydroorotate dehydrogenase (PfDHODH) inhibitor I that is potent (KI = 15 nM) and species-selective (>5000-fold over the human enzyme) was identified by high-throughput screening. The substituted triazolopyrimidine and its structural analogs were produced by an inexpensive three-step synthesis, and the series showed good association between PfDHODH inhibition and parasite toxicity. This study has identified the first nanomolar PfDHODH inhibitor with potent antimalarial activity in whole cells (EC50 = 79 nM).

Journal of Medicinal Chemistry published new progress about Antimalarials. 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, Recommanded Product: 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine.

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

Singh, Anju published the artcileQuinoline carboxamide core moiety-based compounds inhibit P. falciparum falcipain-2: Design, synthesis and antimalarial efficacy studies, Computed Properties of 24415-66-5, the main research area is Plasmodium falcipain quinoline carboxamide based compound antimalarial; Drug development; Falcipain-2 (FP2); Malaria; P. falciparum; Quinoline carboxamide.

Targeting Falcipain-2 (FP2) for the development of antimalarials is a promising and established concept in antimalarial drug discovery and development. FP2, a member of papain-family cysteine protease of the malaria parasite Plasmodium falciparum holds an important role in Hb degradation pathway. A new series of quinoline carboxamide-based compounds was designed, synthesized and evaluated for antimalarial activity. We integrated mol. hybridization strategy with in-silico drug design to develop FP2 inhibitors. In-vitro results of FP2 inhibition by Qs17, Qs18, Qs20 and Qs21 were found to be in low micromolar range with IC50 4.78, 7.37, 2.14 and 2.64μM, resp. Among the 25 synthesized compounds, four compounds showed significant antimalarial activities. These compounds also depicted morphol. and food-vacuole abnormalities much better than that of E-64, an established FP2 inhibitor. Overall these aromatic substituted quinoline carboxamides can serve as promising leads for the development of novel antimalarial agents.

Bioorganic Chemistry published new progress about Antimalarials. 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, Computed Properties of 24415-66-5.

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

Hameed P, Shahul published the artcileAminoazabenzimidazoles, a Novel Class of Orally Active Antimalarial Agents, Category: triazoles, the main research area is aminoazabenzimidazole preparation SAR antimalarial Plasmodium.

Whole-cell high-throughput screening of the AstraZeneca compound library against the asexual blood stage of Plasmodium falciparum (Pf) led to the identification of amino imidazoles, a robust starting point for initiating a hit-to-lead medicinal chem. effort. Structure-activity relation studies followed by pharmacokinetics optimization resulted in the identification of (I) as an attractive lead with good oral bioavailability. Compound I was efficacious (ED90 of 28.6 mg·kg-1) in the humanized P. falciparum mouse model of malaria (Pf/SCID model). Representative compounds displayed a moderate to fast killing profile that is comparable to that of chloroquine. This series demonstrates no cross-resistance against a panel of Pf strains with mutations to known antimalarial drugs, thereby suggesting a novel mechanism of action for this chem. class.

Journal of Medicinal Chemistry published new progress about Antimalarials. 502546-41-0 belongs to class triazoles, name is 5-Cyclopropyl-4H-1,2,4-triazol-3-amine, and the molecular formula is C5H8N4, Category: triazoles.

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

Gujjar, Ramesh published the artcileIdentification of a Metabolically Stable Triazolopyrimidine-Based Dihydroorotate Dehydrogenase Inhibitor with Antimalarial Activity in Mice, COA of Formula: C6H5ClN4, the main research area is metabolically stable triazolopyrimidine derivative preparation dihydroorotate dehydrogenase malaria.

Plasmodium falciparum causes 1-2 million deaths annually. Yet current drug therapies are compromised by resistance. We previously described potent and selective triazolopyrimidine-based inhibitors of P. falciparum dihydroorotate dehydrogenase (PfDHODH) that inhibited parasite growth in vitro; however, they showed no activity in vivo. Here we show that lack of efficacy against P. berghei in mice resulted from a combination of poor plasma exposure and reduced potency against P. berghei DHODH. For compounds containing naphthyl (DSM1) or anthracenyl (DSM2), plasma exposure was reduced upon repeated dosing. Phenyl-substituted triazolopyrimidines were synthesized leading to identification of analogs with low predicted metabolism in human liver microsomes and which showed prolonged exposure in mice. Compound 21 (DSM74), containing p-trifluoromethylphenyl, suppressed growth of P. berghei in mice after oral administration. This study provides the first proof of concept that DHODH inhibitors can suppress Plasmodium growth in vivo, validating DHODH as a new target for antimalarial chemotherapy.

Journal of Medicinal Chemistry published new progress about Antimalarials. 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, COA of Formula: C6H5ClN4.

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

Boechat, Nubia published the artcileNew trifluoromethyl triazolopyrimidines as anti-Plasmodium falciparum agents, Formula: C6H5ClN4, the main research area is trifluoromethyl triazolopyrimidine preparation antimalarial SAR.

According to the World Health Organization, half of the World’s population, approx. 3.3 billion people, is at risk for developing malaria. Nearly 700,000 deaths each year are associated with the disease. Control of the disease in humans still relies on chemotherapy. Drug resistance is a limiting factor, and the search for new drugs is important. We have designed and synthesized new 2-(trifluoromethyl)[1,2,4]triazolo[1,5-α]pyrimidine derivatives based on bioisosteric replacement of functional groups on the anti-malarial compounds mefloquine and amodiaquine. This approach enabled us to investigate the impact of: (i) ring bioisosteric replacement; (ii) a CF3 group substituted at the 2-position of the [1,2,4]triazolo[1,5-α]pyrimidine scaffold and (iii) a range of amines as substituents at the 7-position of the of heterocyclic ring; on in vitro activity against Plasmodium falciparum. According to docking simulations, the synthesized compounds are able to interact with P. falciparum dihydroorotate dehydrogenase (PfDHODH) through strong hydrogen bonds. The presence of a trifluoromethyl group at the 2-position of the [1,2,4]triazolo[1,5-α]pyrimidine ring led to increased drug activity. Thirteen compounds were found to be active, with IC50 values ranging from 0.023 to 20 μM in the anti-HRP2 and hypoxanthine assays. The selectivity index (SI) of the most active derivatives 5, 8, 11 and 16 was found to vary from 1,003 to 18,478.

Molecules published new progress about Antimalarials. 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, Formula: C6H5ClN4.

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