34102-79-9

Upstream product

• 61-82-5 3⁽⁵⁾-amino-1,2,4-triazole 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 61-82-5 4H-1,2,4-triazol-3-amine 
• 61-82-5 3-amino-1,2,4-triazole 

Downstream Products

• 1542213-53-5 3-[(2-hydroxyethoxy)methyl]-5-phenyl-1,2,4-triazolo[1,5-a]pyrimidin-7-one 
• 1542213-40-0 3-[(2-acetoxyethoxy)methyl]-5-phenyl-1,2,4-triazolo[1,5-a]pyrimidin-7-one 
• 165820-47-3 N¹-(p-chloro-benzylidene)-(5-phenyl-s-triazolo<1,5-a>pyrimidin-7-yl)-hydrazone 
• 165820-53-1 (5-phenyl-s-triazolo<1,5-a>pyrimidin-7-ylthio)acethydrazide 
• 165820-52-0 ethyl (5-phenyl-s-triazolo<1,5-a>pyrimidin-7-ylthio)acetate 
• 165820-36-0 N¹-benzylidene-(5-phenyl-s-triazolo<1,5-a>pyrimidin-7-yl)-hydrazone 
• 165820-46-2 5-Phenyl-7-piperidin-1-yl-[1,2,4]triazolo[1,5-a]pyrimidine 
• 165820-34-8 Phenyl-(5-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine 
• 165820-45-1 Diethyl-(5-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine 
• 165820-51-9 5-phenyl-s-triazolo<1,5-a>pyrimidin-7(4H)-thione 
• 91092-06-7 7-hydrazino-5-phenyl-s-triazolo<1,5-a>pyrimidine 
• 28565-43-7 7-chloro-5-phenyl-s-triazolo<1,5-a>pyrimidine 

Relevant academic research and scientific papers

Discovery of the Triazolo[1,5- a]Pyrimidine-Based Derivative WS-898 as a Highly Efficacious and Orally Bioavailable ABCB1 Inhibitor Capable of Overcoming Multidrug Resistance

Targeting P-glycoprotein (ABCB1 or P-gp) has been recognized as a promising strategy to overcome multidrug resistance. Here, we reported our medicinal chemistry efforts that led to the discovery of the triazolo[1,5-a]pyrimidine derivative WS-898 as a highly effective ABCB1 inhibitor capable of reversing paclitaxel (PTX) resistance in drug-resistant SW620/Ad300, KB-C2, and HEK293/ABCB1 cells (IC50 = 5.0, 3.67, and 3.68 nM, respectively), more potent than verapamil and zosuquidar. WS-898 inhibited the efflux function of ABCB1, thus leading to decreased efflux and increased intracellular PTX concentration in SW620/Ad300 cells. The cellular thermal shift assay indicated direct engagement of WS-898 to ABCB1. Furthermore, WS-898 stimulated the ATPase activity of ABCB1 but had minimal effects on cytochrome P450 3A4 (CYP3A4). Importantly, WS-898 increased PTX sensitization in vivo without obvious toxicity. The results suggest that WS-898 is a highly effective triazolo[1,5-a]pyrimidine-based ABCB1 inhibitor and shows promise in reversing ABCB1-mediated PTX resistance.

Applications of alkaloid essramycin and derivative thereof in resisting of plant viruses

The invention relates to applications of alkaloid essramycin and a derivative thereof in resisting of plant viruses, wherein the chemical structural formula of the alkaloid essramycin is represented in the specification, specifically the alkaloid essramyc

Discovery of tofacitinib derivatives as orally active antitumor agents based on the scaffold hybridization strategy

In this work, a novel series of tofacitinib analogs were designed and synthesized based on the scaffold hybridization strategy and then evaluated for their antiproliferative activity toward three gastric cancer cell lines, leading to the identification of compound C18 which exhibited potent inhibitory activity against MGC-803 cell lines with an IC50 value of 2.68 μM. Compound C18 could effectively inhibit the colony formation, suppress the cell migration and induce apoptosis of MGC-803 cells through activating the p38 and JNK signaling pathways, while C18 showed no obvious effect on the cell cycle distribution in MGC-803 cells. In addition, C18 could initiate mitochondrial dysfunction of MGC-803 cells. Besides, in vivo antitumor studies indicated that C18 could inhibit gastric cancer tumor growth in vivo without obvious global toxicity.

Development of Highly Potent, Selective, and Cellular Active Triazolo[1,5- a]pyrimidine-Based Inhibitors Targeting the DCN1-UBC12 Protein-Protein Interaction

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 in-house 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.

Synthesis, structure-activity relationship studies and biological characterization of new [1,2,4]triazolo[1,5-a]pyrimidine-based LSD1/KDM1A inhibitors

The histone lysine specific demethylase 1 (LSD1/KDM1A) is implicated in the development of cancers, targeting LSD1 has been recognized as a promising strategy for cancer therapy. To date, some small-molecule inhibitors are currently being investigated in clinical trials. Herein we report the design, synthesis and biochemical characterization of [1,2,4]triazolo[1,5-a]pyrimidine derivatives as new LSD1 inhibitors. Of these compounds, compound C26 inhibited LSD1 in a reversible manner (IC50 = 1.72 μM) and showed selectivity to LSD1 over MAO-A/B. Besides, compound C26 displayed FAD-competitive binding to LSD1. Interestingly, C26 did not inhibit horseradish peroxidase (HRP) and quench H2O2, thus excluding the possibility that LSD1 inhibition by C26 was due to the HRP inhibition and consumption of H2O2. In LSD1 overexpressed A549 cells, compound C26 concentration-dependently induced accumulation of H3K4me1/me2 and H3K9me2 and showed cellular target engagement to LSD1. Additionally, compound C26 significantly inhibited migration of A549 cells in a concentration-dependent manner, further western blot analysis showed that C26 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 C26 toward LSD1. To conclude, the [1,2,4]triazolo[1,5-a]pyrimidine could serve as a promising scaffold for the development of new LSD1 inhibitors.

Synthesis of certain s-triazolopyrimidines structurally related to some chemotherapeutic agents

5-Phenyl-s-triazolopyrimidin-7(4H)-one (2) was prepared and chlorinated with phosphorus oxychloride to give 7-chloro-5-phenyl-s-triazolopyrimidine (3).Compound 3 was subjected to some sequence reactions to produce other new s-triazolo