149221-33-0Relevant academic research and scientific papers
Vanadium(IV) acetylacetonate catalyzed stereoselective synthesis of β-enaminoesters and β-enaminones
Laskar, Rajibul A.,Begum, Naznin A.,Hedayetullah Mir, Mohammad,Ali, Shahzad,Khan, Abu T.
, p. 436 - 440 (2013/02/23)
An efficient and stereoselective procedure has been described for the synthesis of a series of β-enaminoesters and β-enaminones by vanadium(IV) acetylacetonate [VO(acac)2] catalyzed reaction of β-ketoesters and 1,3-diketones with both aliphatic and aromatic amines. X-ray crystallographic studies of some representative compounds corroborate two types of structural geometry formed by inter-molecular as well as intra-molecular hydrogen bonds.
Synthesis and Anticonvulsant Activity of Enaminone. 2. Further Structure-Activity Correlations.
Scott, K. R.,Edafiogho, Ivan O.,Richardson, Erica L.,Farrar, Vida A.,Moore, Jacqueline A.,et al.
, p. 1947 - 1955 (2007/10/02)
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.
