269065-93-2

Upstream product

• 100-52-7 benzaldehyde 
• 193335-14-7 6-(3,5-dimethylpyrazol-1-yl)-N-(3-methyl-2-pyridyl)-1,2,4,5-tetrazin-3-amine 
• 30169-25-6 3,6-bis-(3,5-dimethyl-pyrazol-1-yl)-1,2,4,5-tetrazine 

Relevant academic research and scientific papers

Synthesis, antitumor evaluation and 3D-QSAR studies of [1,2,4]triazolo[4,3-b][1,2,4,5]tetrazine derivatives

A series of [1,2,4]triazolo[4,3-b][1,2,4,5]tetrazine derivatives have been synthesized and their structures were confirmed by single-crystal X-ray diffraction. Compared to some reported structures of 1,6-dihydro-1,2,4,5-tetrazine, these compounds can't be considered as having homoaromaticity. Their antiproliferative activities were evaluated against MCF-7, Bewo and HL-60 cells in vitro. Two compounds were highly effective against MCF-7, Bewo and HL-60 cells with IC50values in 0.63–13.12?μM. Three-dimensional quantitative structure–activity relationship (3D-QSAR) studies of comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) were carried out on 51 [1,2,4]triazolo[4,3-b][1,2,4,5]tetrazine derivatives with antiproliferative activity against MCF-7 cell. Models with good predictive abilities were generated with the cross validated q2values for CoMFA and CoMSIA being 0.716 and 0.723, respectively. Conventional r2values were 0.985 and 0.976, respectively. The results provide the tool for guiding the design and synthesis of novel and more potent tetrazine derivatives.

Synthesis and biological evaluation of novel 6-alkoxy-3-aryl-[1,2,4]triazolo[4,3-b][1,2,4,5] tetrazines

A series of 6-alkoxy-3-aryl-[1,2,4]triazolo[4,3-b][1,2,4,5] tetrazine derivatives is synthesized and evaluated for their antitumor activities. These compounds exhibit potent antiproliferative activities against A549, Bewo, and MCF-7 cells. Molecular docking is performed to study the inhibitor–c-Met kinase interactions, and the results show that 6-ethoxyl-3-phenylethyl-[1,2,4]triazolo[4,3-b][1,2,4,5] tetrazine is potently bound to c-Met kinase with two hydrogen bonds and one π–π interaction. Based on these preliminary results, it is thought that compound 6-ethoxyl-3-phenylethyl-[1,2,4]triazolo[4,3-b][1,2,4,5] tetrazine with potent inhibitory activity may be a potential anticancer agent.

Pyrazole as a leaving group in nucleophilic substitution in 3,6-bis(3,5-dimethyl-1-pyrazolyl)-1,2,4,5-tetrazines

Nucleophilic substitution by N-nucleophiles of the 3,5-dimethyl-1-pyrazolyl group in 3,6-bis-(3,5-dimethyl-1-pyrazolyl)-1,2,4,5-tetrazine is discussed.