39573-73-4

Upstream product

• 142954-77-6 5-phenyl-4,7-dihydro-1,2,4-triazolo<1,5-a>pyrimidine 
• 61-82-5 3-amino-1,2,4-triazole 
• 879-72-1 3-(dimethylamino)propiophenone hydrochloride 
• 1201-93-0 1-phenyl-3-dimethylaminoprop-2-enone 
• 98-80-6 phenylboronic acid 
• 3506-36-3 3-dimethylaminopropiophenone 

Relevant academic research and scientific papers

Synthesis of New [1,2,4]Triazolo[1,5-a]pyrimidine Derivatives: Reactivity of 3-Amino[1,2,4]triazole towards Enaminonitriles and Enaminones

A diversity of new 7-substituted[1,2,4]triazolo[1,5-a]pyrimidine and 6-substituted[1,2,4]triazolo[1,5-a]pyrimidine-7-amine derivatives has been synthesized via reaction of 3-amino-[1,2,4]triazole with enaminonitriles and enaminones. The regio orientation and the structure of the products were confirmed by spectral and analytical data and synthesis via an alternative route. The procedure proved to be simple, efficient, and high yielding, and diversities of [1,2,4]triazolo[1,5-a]pyrimidines were obtained.

Synthesis, characterization and cytotoxicity studies of 1,2,3-triazoles and 1,2,4-triazolo [1,5-a] pyrimidines in human breast cancer cells

Vascular endothelial growth factor (VEGF) and its receptor (VEGFR) is essential for physiological functions of tissues and neovasculature. VEGFR signaling is associated with the progression of pathological angiogenesis in various types of malignancies, making it an attractive therapeutic target in cancer treatment. In the present work, we report the synthesis of 1,4-disubstituted 1,2,3-triazoles and 1,2,4-triazolo[1, 5-a]pyrimidine derivatives via copper (I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction and screened for their anticancer activity against MCF7 cells. We identified 1-(2′-ethoxy-4′-fluoro-[1,1′-biphenyl]-4-yl)-4-phenyl-1H-1,2,3-triazole (EFT) as lead cytotoxic agent against MCF7 cell lines with an IC50 value of 1.69 μM. Further evaluation revealed that EFT induces cytotoxicity on Ishikawa, MDA-MB-231 and BT474 cells with IC50 values of 1.97, 4.81 and 4.08 μM respectively. However, EFT did not induce cytotoxicity in normal lung epithelial (BEAS-2B) cells. Previous reports suggested that 1,2,3-triazoles are the inhibitors of VEGFR1 and therefore, we evaluated the effect of EFT on the expression of VEGFR1. The results demonstrated that EFT downregulates the expression of VEGFR1 in MCF7 cells. In summary, we identified a potent cytotoxic agent that imparts its antiproliferative activity by targeting VEGFR1 in breast cancer cells. The novel compound could serve as a lead structure in developing VEGFR1 inhibitors.

The synthesis and evaluation of triazolopyrimidines as anti-tubercular agents

We identified a di-substituted triazolopyrimidine with anti-tubercular activity against Mycobacterium tuberculosis. Three segments of the scaffold were examined rationally to establish a structure-activity relationship with the goal of improving potency and maintaining good physicochemical properties. A number of compounds displayed sub-micromolar activity against Mycobacterium tuberculosis with no cytotoxicity against eukaryotic cells. Non-substituted aromatic rings at C5 and a two-carbon chain connecting a terminal aromatic at C7 were preferred features; the presence of NH at C7 and a lack of substituent at C2 were essential for potency. We identified compounds with acceptable metabolic stability in rodent and human liver microsomes. Our findings suggest that the easily-synthesized triazolopyrimidines are a promising class of potent anti-tubercular agents and warrant further investigation in our search for new drugs to fight tuberculosis.

The application of unsymmetrical vinylogous iminium salts and related synthons to the preparation of monosubstituted triazolo[1,5-a]pyrimidines

The reaction of vinylogous iminium salts and related analogs with 3-amino-1,2,4-triazole to yield 7-substituted and 5-substituted triazolo[1,5-a]pyrimidines is described.

IMINE-ENAMINE TAUTOMERISM OF DIHYDROAZOLOPYRIMIDINES. 3. 5-ARYL-SUBSTITUTED 4,7(6,7)-DIHYDRO-1,2,4-TRIAZOLOPYRIMIDINES

5-Aryl-substituted 4,7(6,7)-dihydro-1,2,4-triazolopyrimidines were obtained by condensation of 3-amino-1,2,4-triazole with β-dimethylaminopropiophenone hydrochlorides or crotophenone.The effect of steric and electronic factors on the position of th