2503-56-2

Basic information

• Product Name: 7-Hydroxy-5-methyl-1,3,4-triazaindolizine
• Synonyms: 2,4]Triazolo[1,5-a]pyrimidin-7-ol,5-methyl-[1;5-a)pyrimidin-7-ol,5-methyl-s-triazolo(;5-Methyl-7-hydroxy-1,3,4-triazindolizine;5-Methyl-s-trazolo[1,5-]pyrimidin-7-ol;Methyl hydroxytriazaindolizine;s-Triazolo(1,5-a)pyrimidin-7-ol, 5-methyl-;BUTTPARK 125\40-15;7-HYDROXY-5-METHYL-[1,2,4]TRIAZOLO[2,3-A]PYRIMIDINE
• CAS NO: 2503-56-2
• Molecular Formula: C₆H₆N₄O
• Molecular Weight: 149.15
• EINECS: 219-706-7
• Product Categories: Industrial/Fine Chemicals;Benzotriazoles;Building Blocks;C-C Bond Formation;Chemical Synthesis;Heterocyclic Building Blocks;Others;Synthetic Reagents
• Mol File: 2503-56-2.mol
• Article Data: 13

Chemical Properties

• Melting Point: 280-283 °C(lit.)
• Boiling Point: 271.66°C (rough estimate)
• Appearance: white fine crystalline powder
• Density: 1.3471 (rough estimate)
• Vapor Pressure: 0-0Pa at 20-25℃
• Refractive Index: 1.6700 (estimate)
• Storage Temp.: 2-8°C
• PKA: 1.14±0.53(Predicted)
• Water Solubility: INSOLUBLE IN COLD WATER
• BRN: 609440
• CAS DataBase Reference: 7-Hydroxy-5-methyl-1,3,4-triazaindolizine(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Hydroxy-5-methyl-1,3,4-triazaindolizine(2503-56-2)
• EPA Substance Registry System: 7-Hydroxy-5-methyl-1,3,4-triazaindolizine(2503-56-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 1
• RTECS: XZ6133300
• F: 9
• TSCA: Yes
• Hazardous Substances Data: 2503-56-2(Hazardous Substances Data)

Usage

Chemical Properties

7-Hydroxy-5-methyl-1,3,4-triazaindolizine is white fine crystalline powder

Uses

Different sources of media describe the Uses of 2503-56-2 differently. You can refer to the following data:
1. Reactant for the synthesis of: ? ;Ruthenium(II)-Hmtpo complexes1? ;Dihydroorotate dehydrogenase inhibitors with antimalarial activity2Reactant for the Vilsmeier reaction of conjugated carbocycles and heterocycles3Investigations of the pharmacological activity caused by binding to HIV TAR RNA4Additive to study the space charge layer in silver bromide microcrystals5
2. Reactant for the synthesis of: Ruthenium(II)-Hmtpo complexesDihydroorotate dehydrogenase inhibitors with antimalarial activityReactant for the Vilsmeier reaction of conjugated carbocycles and heterocyclesInvestigations of the pharmacological activity caused by binding to HIV TAR RNAAdditive to study the space charge layer in silver bromide microcrystals

InChI:InChI=1/C7H7N3O/c1-5-2-6(11)3-7-8-4-9-10(5)7/h2-4,11H,1H3

Upstream product

• 61-82-5 3⁽⁵⁾-amino-1,2,4-triazole 
• 141-97-9 ethyl acetoacetate 
• 61-82-5 3-amino-1,2,4-triazole 
• 61-82-5 4H-1,2,4-triazol-3-amine 

Downstream Products

• 33376-96-4 5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine 
• 898478-91-6 (2-fluorophenyl)(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amine 
• 56347-09-2 5-methyl-7-phenyl-[1,2,4]triazolo[1,5-a]pyrimidine 

Relevant articles and documents

Quinoline carboxamide core moiety-based compounds inhibit P. falciparum falcipain-2: Design, synthesis and antimalarial efficacy studies

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 hemoglobin degradation pathway. A new series of quinoline carboxamide-based compounds was designed, synthesized and evaluated for antimalarial activity. We integrated molecular 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 2.64 μM, respectively. Among the 25 synthesized compounds, four compounds showed significant antimalarial activities. These compounds also depicted morphological 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.

Pd-catalyzed Suzuki/Sonogashira cross-coupling reaction and the direct sp3 arylation of 7-chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

A rapid and efficient method is 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.

Rational design, synthesis and biological screening of triazine-triazolopyrimidine hybrids as multitarget anti-Alzheimer agents

In our endeavor towards the development of potent multitarget ligands for the treatment of Alzheimer's disease, a series of triazine-triazolopyrimidine hybrids were designed, synthesized and characterized by various spectral techniques. Docking and scoring techniques were used to design the inhibitors and to display their interaction with key residues of active site. Organic synthesis relied upon convergent synthetic routes were mono and di-substituted triazines were connected with triazolopyrimidine using piperazine as a linker. In total, seventeen compounds were synthesized in which the di-substituted triazine-triazolopyrimidine derivatives 9a-d showed better acetylcholinesterase (AChE) inhibitory activity than the corresponding tri-substituted triazine-triazolopyrimidine derivatives 10a-f. Out of the disubstituted triazine-triazolopyrimidine based compounds, 9a and 9b showed encouraging inhibitory activity on AChE with IC50 values 0.065 and 0.092?μM, respectively. Interestingly, 9a and 9b also demonstrated good inhibition selectivity towards AChE over BuChE by ～28 folds. Furthermore, kinetic analysis and molecular modeling studies showed that 9a and 9b target both catalytic active site as well as peripheral anionic site of AChE. In addition, these derivatives effectively modulated Aβ self-aggregation as investigated through CD spectroscopy, ThT fluorescence assay and electron microscopy. Besides, these compounds exhibited potential antioxidants (2.15 and 2.91 trolox equivalent by ORAC assay) and metal chelating properties. In silico ADMET profiling highlighted that, these novel triazine derivatives have appropriate drug like properties and possess very low toxic effects in the primarily pharmacokinetic study. Overall, the multitarget profile exerted by these novel triazine molecules qualified them as potential anti-Alzheimer drug candidates in AD therapy.