16876-54-3

Upstream product

• 67263-27-8 2,4,6-trinitro-1-piperidinobenzene 
• 75-31-0 isopropylamine 
• 88-88-0 2,4,6-trinitrochlorobenzene 
• 77379-02-3 2,4,6-trinitro-1-pyrrolidinobenzene 
• 131170-45-1 1-(N-Methyl)butylamino-2,4,6-trinitrobenzene 
• 88-89-1 2,4,6-Trinitrophenol 
• 13029-07-7 1-diethylamino-2,4,6-trinitro-benzene 
• 2493-31-4 N,N-dimethyl-2,4,6-trinitro-aniline 

Relevant academic research and scientific papers

1H NMR Studies of Proton Transfer and ?-Complex Formation in the Reactions of N-Substituted Picramides with Oxygen and Nitrogen Bases

1H NMR measurements of N-substituted picramides in dimethyl sulphoxide-methanol containing sodium methoxide show that the two major modes of 1:1 interaction involve transfer of an amino proton to give the conjugate base or methoxide attack at the 3-position to give a ?-adduct.The proportion of parent reacting by the latter pathway increases as the proportion of methanol in the solvent increases.Some comparative measurements in isopropanol-dimethyl sulphoxide show that relative to methoxide the isopropoxide ion has a greater propensity abstraction than for base addition.Reaction of the substrates with amide ions derived from piperidine or from benzylamine gives ?-complexes by attack at unsubstituted ring positions.In the benzylamide adducts spin coupling is observed between the amino proton and the adjacent ring and methylene protons.

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.].

Aromatic nucleophilic substitution reactions of 1-dialkylamino-substituted activated benzenes with various amines in dimethyl sulfoxide

In the reactions of 1-dlalkylamino-2,4,6-trinitro- and 1-dialkylamlno-2, 4-dinitrobenzenes with various amines in dimethyl sulfoxide, 1-dialkylamino group is easily replaced with primary n-alkylamines at room temperature, and in a low yield with pyrrolidine only among secondary amines.