312593-08-1

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 24848-20-2 4-amino-2,4-dihydro-5-trifluoromethyl-3H-1,2,4-triazole-3-thione 
• 24848-20-2 4-amino-5-trifluoromethyl-4H-1,2,4-triazole-3-thiol 

Downstream Products

• 1224727-27-8 C₂₈H₂₈F₆N₁₀O₂S₂ 
• 1224727-13-2 C₂₀H₂₁F₃N₈OS 
• 1224727-16-5 C₂₁H₂₃F₃N₈OS 
• 1224727-22-3 C₂₂H₂₅F₃N₈OS 
• 1335203-78-5 C₂₃H₂₃Cl₂F₃N₆OS 
• 1335203-72-9 C₂₃H₂₄ClF₃N₆OS 
• 1335203-66-1 C₂₃H₂₅F₃N₆OS 

Relevant academic research and scientific papers

VEGFR2 and hepatocellular carcinoma inhibitory activities of trisubstituted triazole derivatives

The vascular endothelial growth factor receptor 2 (VEGFR2) is considered as a significant target for inhibition in the discovery of novel molecules with anti-proliferative activity. Here, we report the synthesis of novel derivatives of 1,2,4-triazole as potent VEGFR2 inhibitors with anti-HCC activity. The chemical structures of the target triazole derivatives were assured through elemental and spectral analysis. The in vitro anti-VEGFR2 activity of the new compounds was evaluated. Most compounds revealed promising inhibitory activity in comparison to Sorafenib (IC50= 0.088 μM). The triazolothiadiazine derivative 7a was the most active one (IC50= 0.057 μM). Also, the phenylhydrazono triazole derivatives 11c, 13b, and 13c showed potent activities (IC50= 0.074–0.124 μM) that were comparable to that of Sorafenib. Moreover, the anti-proliferative activity of most active compounds was assessed against two HCC cell lines and against normal hepatic cells THLE3. Compound 7a showed superior activity to Sorafenib; 2 times its activity against HepG2 and 15.5 times against Huh7. Furthermore, compound 13c was comparable to sorafenib against HepG2 and 4.1 times against Huh7. Besides, these potent compounds displayed higher safety profiles than Sorafenib against the normal THLE3 cells. In addition, docking simulation demonstrated good fitting with strong binding interactions within the VEGFR2 ATP binding site. In silico ADME calculations showed good GI absorption and high oral bioavailability of compound 7a.

Synthesis, structure and biological activity of novel 1,2,4-triazole Mannich bases containing a substituted benzylpiperazine moiety

A series of novel Mannich bases with trifluoromethyl-1,2,4-triazole and substituted benzylpiperazine moieties were synthesized. Their structures were confirmed by IR, 1H NMR and elemental analysis. The single crystal structure of compound 4r was also determined. The preliminary bioassays showed that most of the lead compounds had low herbicidal activity against Brassica campestris, Echinochloa crusgalli, and KARI enzyme. However, most of them exhibited significant fungicidal activity at the dosage of 50μg/mL toward five test fungi. Among the 18 novel compounds, several showed superiority over the commercial fungicide Triadimefon against Cercospora arachidicola and Fusarium oxysporum f. sp. cucumerinum during this study. Meanwhile, some compounds displayed plant growth regulatory activity at the dosage of 10μg/mL.

Synthesis and biological activity of some novel trifluoromethyl-substituted 1,2,4-triazole and bis(1,2,4-Triazole) mannich bases containing piperazine rings

A series of trifluoromethyl-substituted 1,2,4-triazole Mannich base 6 and bis(1,2,4-triazole) Mannich base 7 containing pyrimidinylpiperazine rings via the Mannich reaction were synthesized and characterized by infrared (IR), 1H nuclear magnetic resonance (NMR), and elemental analysis. The fungicidal tests indicated that most of compounds 6 and 7 possessed excellent fungicidal activity. Among 19 novel compounds, some showed superiority over commercial fungicides Dimethomorph, Thiophanate-methyl, Iprodione, and Zhongshengmycin. Some compounds also exhibited favorable herbicidal activity in the preliminary studies. On the basis of the comparative molecular field analysis (CoMFA), five novel compounds were subsequently synthesized, their activities were estimated fairly accurately, and compounds 6-A1 and 7-A2 displayed good fungicidal activity against Pseudoperonospora cubensis (96.9 and 84.9%) as 6h and 7c, respectively.