149221-05-6

Usage

InChI:InChI=1/C16H19NO3/c1-11-8-13(9-14(18)15(11)16(19)20-2)17-10-12-6-4-3-5-7-12/h3-7,9,11,15,17H,8,10H2,1-2H3

Upstream product

• 625-33-2 3-penten-2-one 
• 39493-30-6 methyl 2-hydroxy-6-methyl-4-oxocyclohex-2-enecarboxylate 
• 100-46-9 benzylamine 
• 56157-27-8 methyl 6-methyl-2,4-cyclohexanedione-1-carboxylate 
• 39493-62-4 2-oxo-4-hydroxy-6-methyl-cyclohex-3-ene carboxylic acid methyl ester 

Downstream Products

• 1158819-88-5 C₂₅H₂₃NO₆ 

Relevant academic research and scientific papers

Partially saturated indeno[1,2-b]indole derivatives via deoxygenation of heterocyclic α-hydroxy-N,O-hemiaminals

A series of 3-aminocyclohex-2-enones were reacted with indane-1,2,3-trione monohydrate (ninhydrin) yielding 4b,9b-dihydroxyindeno[ 1,2-b]indoles that were deoxygenated to indeno[1,2-b]indoles. Georg Thieme Verlag Stuttgart.

Anticonvulsant evaluation and mechanism of action of benzylamino enaminones

The mechanism of anticonvulsant action was evaluated for the benzylamino enaminones. The most potent enaminone in this series was the unsubstituted benzylamine analog (30; methyl 4-benzylamino-6-methyl-2-oxocyclohex-3-en-1-oate) which had an oral effective dose (ED50) in rats of 27 mg/kg against maximal electroshock seizures, and a concentration 10-fold less than this dose depressed excitatory synaptic transmission, and action potential firing in the rat brain in vitro.

Ultraviolet spectroscopy of anticonvulsant enaminones.

The ultraviolet (UV) spectra of selected enaminones were determined in acidic, alkaline and neutral media and compared to their anticonvulsant activities. The wavelength of maximum absorption and molar absorptivity were compared with the anticonvulsant ac

Synthesis, reactions, and preliminary evaluations of enaminone esters

The objective of this work was to design enaminone esters that would possess potential medicinal properties. The reaction between β-hydroxyketo esters and primary or secondary amines yielded secondary or tertiary enaminone esters, respectively. The UV spe

Synthesis and Anticonvulsant Activity of Enaminone. 2. Further Structure-Activity Correlations.

This report continues the in-depth evaluation of methyl 4--6-methyl-2-oxocyclohex-3-en-1-oate, 1 (ADD 196022), and methyl 4-(benzylamino)-6-methyl-2-oxocyclohex-3-en-1-oate, 2, two potent anticonvulsant enaminones.These compounds were evaluated employing the amygdala kindling model.Neither 1 nor 2 was active against amygdala kindled seizures, further supporting the corneal kindled model as a definitive tool for antielectroshock seizure evaluation as previously reported.Additional intraperitoneal (ip) data on 1 revealed toxicity at 24 h at 100 mg/kg.Several active analogs have been prepared with the view to minimizing toxicity.In a special ip rat screen developed by the Antiepileptic Drug Development (ADD) Program, these newer analogs were evaluated for protection against maximal electroshock seizures (MES) at 10 mg/kg and neurotoxicity at 100 mg/kg.From this screen, several compounds were shown to be safer alternatives, the most notable was methyl 4--6-methyl-2-oxocyclohex-3-en-1-oate, 13.Compound 13 had an ip ED50 of 4 mg/kg in the rat and a TD50 of 269 mg/kg, providing a protective index (TD50/ED50) of > 67.By variation in the ring size, additional aromatic substitutions and the synthesis of acyclic analogs, these newer compounds provide a more definitive insight into the structure-activity correlation.CLOGP evaluation and molecular modeling studies are also provided to further elaborate the molecular characteristics of potential anticonvulsant enaminones.

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