18888-58-9

Upstream product

• 6973-40-6 2,4,6-trinitrophenyl phenyl ether 
• 536-90-3 m-Anisidine 
• 88-88-0 2,4,6-trinitrochlorobenzene 
• 88-89-1 2,4,6-Trinitrophenol 

Relevant academic research and scientific papers

Synthesis and biological evaluation of 2,4,6-trinitroaniline derivatives as potent antitumor agents

Abstract: Nitro group-containing compounds are well known as effective anticancer drugs. The aim of the study is to synthesize a series of trinitroaniline derivatives to determine their potential antitumor activities on diverse cancer cell models, anti-apoptotic and anti-metastatic features on hepatoma cells. The anti-proliferative studies show that IC50 values of N-phenyl-2,4,6-trinitroaniline, N-(2,4,6-trinitrophenyl)naphthalen-1-amine, N-(2,4,6-trinitrophenyl)naphthalen-2-amine, N-(3-nitrophenyl)-2,4,6-trinitroaniline were similar to IC50 value of cisplatin in Hep3B cells. In fact, IC50 value of N-(3,5-difluorophenyl)-2,4,6-trinitroaniline is better than cisplatin. In addition, all compounds could decrease the expression of the cell cycle checkpoint protein cyclin D1. To investigate the effect of compounds on the apoptotic pathway, mRNA and protein expressions of Bcl-2 and Bax were analyzed with qRT-PCR and Western blot. Annexin V staining assay, apoptotic mRNA and protein analysis indicate that N-isopropyl-2,4,6-trinitroaniline, N-(2,4,6-trinitrophenyl)-5-methylisoxazole-3-amine, N-(3-nitrophenyl)-2,4,6-trinitroaniline, N-(4-nitrophenyl)-2,4,6-trinitroaniline induce intrinsic apoptosis by increasing the ratio of Bax/Bcl-2 expression. In addition, colony formation and wound healing assays confirmed that these compounds also inhibit the metastatic activity of Hep3B cells. 2,4,6-Trinitroaniline derivatives, especially N-(3-nitrophenyl)-2,4,6-trinitroaniline might be used as candidate for the development of new antitumor drugs. Graphic abstract: [Figure not available: see fulltext.].

Mechanism of the Reactions of Substituted Anilines with Phenyl 2,4,6-Trinitrophenyl Ether in Benzene: Evidence for a Cyclic Transition State involving an Eight-membered Ring

Rates and activation parameters have been determined for the reactions of phenyl 2,4,6-trinitrophenyl ether with substituted anilines in benzene.For some of the nucleophiles, the rates decrease with increasing temperature in the range 5-35 deg C resulting in negative activation enthalpies (ΔH(excit.) -3.1 to -27.3 kJ mol-1).This is strong evidence for a stepwise mechanism involving (at least) a pre-equilibrium.These base-catalysed nucleophilic substitution reactions are sensitive to the nature of the arylated amine as indicated by the Hammett's constant (ρ -7.7).