78002-38-7

Upstream product

• 106-40-1 4-bromo-aniline 
• 110-20-3 acetone semicarbazone 
• 1967-25-5 4-bromophenylurea 
• 2646-26-6 4-(4-bromophenyl)semicarbazide 
• 67-64-1 acetone 

Downstream Products

• 78002-42-3 4-(4-Bromo-phenyl)-5,5-dimethyl-4,5-dihydro-[1,2,4]triazol-3-one 

Relevant academic research and scientific papers

Synthesis and anticonvulsant activity of 4-bromophenyl substituted aryl semicarbazones

A number of 4-bromophenyl semicarbazones were synthesised and evaluated for anticonvulsant and sedative-hypnotic activities. After intraperitoneal injection to mice, the semicarbazone derivatives were examined in the maximal electroshock seizure (MES), subcutaneous pentylenetetrazole (scPTZ), subcutaneous strychnine (scSTY) and neurotoxicity (NT) screens. All the compounds showed anticonvulsant activity in one or more test models. Compound 12 showed greatest activity, being active in all the screens with very low neurotoxicity and no sedative-hypnotic activity. All the compounds except 7 had lower neurotoxicity compared to phenytoin. Three compounds (6, 11 and 14) showed greater protection than Sodium valproate. The essential structural features responsible for interaction with receptor site are established within a suggested pharmacophore. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

Synthesis and antitumour evaluation of 4-bromophenyl semicarbazones

4-Bromophenyl semicarbazone derivatives have been synthesized and their chemical structures have been confirmed by means of their IR, 1H-NMR data and by elemental analyses. The in vitro evaluation in the 3-cell line, one dose primary anticancer assay is described. The 4-bromo substituted p-nitrobenzylidene phenyl semicarbazone (5) showed significant activity against breast MCF7 cell line and was further evaluated for potential anticancer activity in an in vitro human disease-oriented tumour cell line screening panel that consisted of 59 human tumour cell lines arranged in nine subpanels, representing diverse histologies. Melanoma UACC-62 cell line was relatively more sensitive to compounds 5 (growth inhibition: GI50 = 15.3 μmol/l).

Thermolysis of 5,5-dimethyl-4-aryl-Δ1-1,2,4-triazolin-3-ones in solution. Products, kinetics, substituent effects, and solvent effects

A series of 5,5-dimethyl-4-Δ1-1,2,4-triazolin-3-ones (Ar=C6H5, p-C6H4CH3, p-C6H40CH3,p-C6H4Cl, and p-C6H4Br) were prepared from the corresponding 4-arylsemicarbazones of acetone by oxidative cyclization on alumina.The triazolines decompose in solution to N2,CO, and isopropylidene aryl amine, with first order kinetics, in the temperature range 148-200 deg C.Average activation parameters are ΔH*=35 kcal*mol-1 and ΔS*=8 cal*K-1*mol-1.Substituent effects are correlated through Σ-constants but the thermolyses are relatively insensitive to substituents, with p=-0.17 at 172.5 deg C.Solvent effects indicate a transition state that is less polar than the ground state.It is tentatively concluded that the triazolinone fragmentation, like the analogous thermolysis of a Δ3-1,3,4-oxadiazolin-2-one, may be a fully-concerted but nonsynchronous process with a transition state involving little, if any, charge separation.Other mechanisms, except for those involving highly polar (e.g. zwitterionic) transition states, have not been ruled out.