32675-48-2Relevant academic research and scientific papers
A kinetic study of the high temperature rearrangement of 4-ethyl-3,5-diphenyl-4H-1,2,4-triazole
Gautun,Carlsen
, p. 955 - 959 (2001)
The kinetics of the thermal rearrangement 4-ethyl-3,5-diphenyl-4H-1,2,4-triazoles, 1, to the corresponding 1-ethyl-3,5-diphenyl-l-alkyl-1H-1,2,4-triazoles, 2, was studied in 15-Crown-5 and octadecane at 3130 °C. The reaction was very slow in octadecane but proceed well in 15-Crown-5. The reaction order for the reaction was not constant but changed from an initial second order rate law towards a first order rate law as the reaction progressed. This was confirmed by the concentration dependent reaction order, nc, which was larger than the time dependent rate law, nt. The rationale for the observation was, that at high substrate concentrations the reaction order was second order while at lower concentrations a competing solvent assisted reaction plays an increasing important role. The data were in agreement with a mechanism in which the neutral 4-alkyl-triazoles in an intermolecular nucleophilic displacement reaction form a triazolium triazolate, which in a subsequent nucleophilic reaction gives the observed product.
Development of novel liver?X?receptor modulators based on a 1,2,4-triazole scaffold
Goher, Shaimaa S.,Griffett, Kristine,Hegazy, Lamees,Elagawany, Mohamed,Arief, Mohamed M.H.,Avdagic, Amer,Banerjee, Subhashis,Burris, Thomas P.,Elgendy, Bahaa
, p. 449 - 453 (2019/01/04)
Liver X Receptor (LXR) agonists have been reported as a potential treatment for atherosclerosis, Alzheimer's disease and hepatitis C virus (HCV) infection. We have designed and synthesized a series of potent compounds based on a 1,2,4-triazole scaffold as novel LXR modulators. In cell-based cotransfection assays these compounds generally functioned as LXR agonists and we observed compounds with selectivity towards LXRα (7-fold) and LXRβ (7-fold) in terms of potency. Assessment of the effects of selected compounds on LXR target gene expression in HepG2 cells revealed that compounds 6a-b and 8a-b behaved as inverse agonists on FASN expression even though they were agonists in the LXRα and LXRβ cotransfection assays. Interestingly, these compounds had no effect on the expression of SREBP-1c confirming a unique LXR modulator pharmacology. Molecular docking studies and evaluation of ADME properties in-silico show that active compounds possess favorable binding modes and ADME profiles. Thus, these compounds may be useful for in vivo characterization of LXR modulators with unique profiles and determination of their potential clinical utility.
Thermal rearrangement of 4-alkyl-4H-1,2,4-triazoles to 1-alkyl-1H-1,2,4-triazoles - A study of the mechanism by cross-over experiments
Gautun, Odd R.,Carlsen, Per H. J.
, p. 3745 - 3748 (2007/10/03)
The mechanism for the thermal rearrangement of 4-alkyl-1,2,4-triazoles to the corresponding 1-alkyl-1,2,4-triazoles, was studied by cross-over experiments with mixtures of 4-ethyl-3,5-diphenyl-4H-1,2,4-triazole and 3,5-bis(4-methylphenyl)-4-propyl-4H-1,2,
Transition States in the Crystalline Phase? Thermal Rearrangements of Solid 4H-1,2,4-Triazoles
Carlsen, Per H. J.,Joergensen, Kare B.,Gautun, Odd Reidar,Jagner, Susan,Hakansson, Mikael
, p. 676 - 682 (2007/10/03)
In the crystalline state the 4-methyl and 4-ethyl substituted 4H-1,2,4-triazoles were found to undergo thermal rearrangement to the corresponding 1-alkyl substituted triazoles.The same reaction took place in the melts.Reaction rates were measured in both
Substituent Effects in the Rearrangement of 4-Alkyl-4H-1,2,4-triazoles
Gautun, Odd Reidar,Carlsen, Per H. J.
, p. 411 - 416 (2007/10/02)
A study of the thermal rearrangement of neat 4-alkyl-substituted 4H-1,2,4-triazoles to the corresponding 1-alkyl-1H-1,2,4-triazoles showed that the rearrangement was accompanied by formation of 3,5-diphenyl-1H-1,2,4-triazole and alkenes.The composition of
Synthesis and reactions of 1,6-diaryl-2,5-bis(diazo)-1,3,4,6- tetraoxohexanes
Rubin, Mordecai B.,Bargurie, Moshe,Kosti, Sonia,Kaftory, Menahem
, p. 2670 - 2677 (2007/10/02)
The title compounds were obtained in about 50% yields by reaction of the corresponding diaryltetraoxohexanes with dinitrogen trioxide. A mechanism to account for their formation is proposed. Thermal decompositions of bis-diazo-compounds in the solid state
