[1,2,4]Triazolo[1,5-a]pyrimidine

Base Information

• Chemical Name: [1,2,4]Triazolo[1,5-a]pyrimidine
• CAS No.: 275-02-5
• Molecular Formula: C5H4 N4
• Molecular Weight: 120.11
• Hs Code.: 2933990090
• European Community (EC) Number: 626-056-1
• DSSTox Substance ID: DTXSID50181914
• Nikkaji Number: J590.752G
• Wikidata: Q83052558
• Mol file: 275-02-5.mol

Synonyms:1,2,4-triazolo(1,5-a)pyrimidine

Chemical Property of [1,2,4]Triazolo[1,5-a]pyrimidine

Chemical Property:

• Melting Point: 142-145 °C(lit.)
• Boiling Point: °Cat760mmHg
• PKA: 0.70±0.30(Predicted)
• Flash Point: °C
• PSA: 43.08000
• Density: 1.48 g/cm³
• LogP: 0.12430
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 120.043596145
• Heavy Atom Count: 9
• Complexity: 105

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,2,4-Triazolo[1,5-a]pyrimidine 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A poison.
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CN2C(=NC=N2)N=C1
• General Description: 1,2,4-Triazolo[1,5-a]pyrimidine derivatives, particularly those with specific substitutions at the 2-, 5-, and 7-positions, have been identified as potent and selective inhibitors of *Leishmania (Leishmania) amazonensis* arginase, a key enzyme in the parasite's survival pathway. Among these, 1,2,4-TRIAZOLO[1,5-A]PYRIMIDINE with a trifluoromethyl group at the 2-position and a hydrazinecarbothioamide at the 7-position demonstrated strong non-competitive inhibition, showing high selectivity for the parasitic enzyme over mammalian arginase. This highlights its potential as a promising scaffold for developing targeted anti-leishmanial therapies.

Technology Process of [1,2,4]Triazolo[1,5-a]pyrimidine

There total 11 articles about [1,2,4]Triazolo[1,5-a]pyrimidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

3(5)-amino-1,2,4-triazole (61-82-5) + malonaldehydebis(dimethylacetal) (102-52-3) → 1-deaza-5-azapurine (275-02-5)

Guidance literature:

With acetic acid; for 1h; regioselective reaction; Reflux;

DOI:10.1002/mrc.2634

Reference yield: 82.0%

3-amino-1,2,4-triazole (61-82-5) + 3-dimethylaminoacrolein (927-63-9) → 1-deaza-5-azapurine (275-02-5)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; for 2h; Reflux;

DOI:10.1002/jhet.3222

Reference yield: 74.0%

3(5)-amino-1,2,4-triazole (61-82-5) + malondialdehyde bis(diethyl acetal) (122-31-6) → 1-deaza-5-azapurine (275-02-5)

Guidance literature:

With acetic acid; for 1.5h; Heating;

upstream raw materials:

2-pyrimidinylhydrazine

formic acid

[1,2,4]triazolo[4,3-a]pyrimidine

7-chloro-[1,2,4]triazolo[1,5-a]pyrimidine

Downstream raw materials:

7-phenyl-1,2,4-triazolo<1,5-a>pyrimidine

7-(4-chlorophenyl)-1,2,4-triazolo<1,5-a>pyrimidine

Refernces

Novel Selective Inhibitor of Leishmania (Leishmania) amazonensis Arginase

10.1111/cbdd.12566

This study investigates the potential of [1,2,4]triazolo[1,5-a]pyrimidine derivatives as selective inhibitors of Leishmania (Leishmania) amazonensis arginase, an enzyme crucial for the parasite's polyamine and trypanothione biosynthesis, making it a promising drug target for leishmaniasis treatment. The researchers synthesized and tested twenty-nine [1,2,4]triazolo[1,5-a]pyrimidine derivatives, focusing on the impact of different substituents at the 2-, 5-, and 7-positions. The compound 2-(5-methyl-2(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)hydrazinecarbothioamide (30), featuring a CF3 group at the 2-position and a hydrazinecarbothioamide at the 7-position, emerged as the most potent arginase inhibitor, exhibiting non-competitive inhibition with Ki and IC50 values of 17 ± 1 μM and 16.5 ± 0.5 μM, respectively. This compound selectively inhibited the parasite's arginase without affecting mammalian arginase, suggesting its potential as a lead compound for developing new anti-leishmaniasis drugs.

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