67174-68-9

Usage

InChI:InChI=1/C10H14O4/c1-3-14-10(13)9-6(2)4-7(11)5-8(9)12/h5-6,9,11H,3-4H2,1-2H3

Upstream product

• 141-97-9 ethyl acetoacetate 
• 623-70-1 ethyl (E)-crotonate 
• 625-33-2 3-penten-2-one 
• 105-53-3 diethyl malonate 
• 10544-63-5 ethyl crotonate 

Downstream Products

• 1147846-73-8 C₁₄H₂₁NO₄ 
• 1147846-74-9 C₁₈H₂₃NO₃ 
• 149221-21-6 4-(4-Bromo-phenylamino)-6-methyl-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester 
• 1147846-94-3 ethyl 4-(3-fluoro-4-morpholinophenylamino)-6-methyl-2-oxocyclohex-3-ene-1-carboxylate 
• 1147846-97-6 ethyl 4-(4-(2-fluoro-4-nitrophenyl)piperazin-1-yl)-6-methyl-2-oxocyclohex-3-ene-1-carboxylate 
• 1147846-92-1 ethyl 4-(((S)-3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methylamino)-6-methyl-2-oxocyclohex-3-ene-1-carboxylate 
• 1586771-91-6 ethyl 4-(2',4'-dibromophenylamino)cyclohex-3-en-6-methyl-2-oxo-1-oate 
• 28520-50-5 2,4-Diacetoxy-6-methylbenzoesaeureethylester 
• 38103-09-2 ethyl 3-chloro-2,4-dihydroxy-6-methylbenzoate 
• 3187-58-4 methyl orsellinate 
• 4341-24-6 5-methylcyclohexan-1,3-dione 

Relevant academic research and scientific papers

Synthesis, neuronal activity and mechanisms of action of halogenated enaminones

Due to the excellent anticonvulsant activity of previously synthesized halogenated enaminones, more disubstituted analogs were synthesized and evaluated in vitro. The new enaminones either had no effect, depressed, or enhanced population spike (PS) amplitude in the rat hippocampus in a concentration-dependent manner. Structure-activity relationship (SAR) analysis indicated that compounds 21 and 25 (with dibromo substituents) were equipotent, and more potent than compound 2 (with dichloro substituents), with compound 25 being the most efficacious of all tested compounds. Both diiodo derivatives 30 and 31 tested produced no significant effect on PS. For PS depression, phenyl substitution on the cyclohexenone ring produced the most efficacious compound 25. PS depressing analogues also depressed evoked excitatory postsynaptic current (EPSC) and action potential firing frequency. Removal of phenyl or methyl group from position 6 on the cyclohexenone ring of enaminone esters produced compound 28 which exhibited pro-convulsant effects. There was no direct correlation between C log P values and anticonvulsant activity of the halogenated enaminones. The mechanisms of anticonvulsant activity were the indirect suppression of excitatory synaptic transmission by enhancing extracellular GABA, and the direct suppression of action potential firing of the neurons.

Synthesis, antibacterial and anticonvulsant evaluations of some cyclic enaminones

Several cyclic enaminone esters were synthesized, characterized, and evaluated for anticonvulsant and antibacterial activities using standardized tests. A series of enaminones were mainly phenyl analogs of anticonvulsant enaminones, while a second series

Synthesis and anticonvulsant activity of enaminones

A new series of novel enaminones has been synthesized from cyclic β- dicarbonyl precursors which were condensed with morpholine, pyrrolidine, phenethylamine, hydrazines, substituted benzyl amines, and substituted anilines. These compounds were subsequentl