Synthesis of aminomethyl-substituted cyclic imide derivatives for evaluation as anticonvulsants

Abstract

A series of aminomethyl-substituted cyclic imides (II) based on the 2,5-pyrrolidinedione (X = CH2, succinimide) and 2,4-imidazolidinedione (X = NH, hydantoin) ring systems have been prepared. The compounds were designed on the basis of a potential interaction in the gamma-aminobutyric acid (GABA) neurotransmitter system and evaluated for anticonvulsant activity. The 3-(aminomethyl)-2,5-pyrrolidinediones were prepared by a dehydration procedure beginning with N-benzyl-2-(aminomethyl)succinic acid, whereas the 3-(aminomethyl)-3-methyl-2,3-pyrrolidinediones were best obtained by fusion of the amine salts of 2-(aminomethyl)-2-methylsuccinic acid. The hydantoin derivative, 5-(aminomethyl)-5-methyl-2,4-imidazolidinedione, was obtained by standard procedures. Although none of the compounds tested showed significant activity against convulsions induced by pentylenetetrazole (PTZ), some showed significant activity against maximal electroshock seizures in mice. Possible reasons for the lack of anti-PTZ activity and directions for further testing are discussed.

N-Chlorination rate of five-membered heterocyclic nitrogen compounds

“…This set of heterocyclic organic compounds of five atoms (Fig. ) and their derivatives, very different chemically but with similar structures, is very interesting from the point of view pharmacologically because of their activity like antiepileptic and anticonvulsants . It is interesting to indicate that the type of substituent at C(5) appears to be extremely important in determining the physiological properties of these compounds…”

“…1) and their derivatives, very different chemically but with similar structures, is very interesting from the point of view pharmacologically because of their activity like antiepileptic and anticonvulsants. [4][5][6][7][8][9] It is interesting to indicate that the type of substituent at C(5) appears to be extremely important in determining the physiological properties of these compounds. [10] Moreover, these heterocyclic compounds and their derivatives are of great interest because they possess other interesting characteristics.…”

Synthesis and anticancer activity evaluation of 3,4-mono- and bicyclosubstituted N -(het)aryl trifluoromethyl succinimides

“…Succinimides represent an important class of organic compounds, both as synthetic intermediates and as biological agents with anticonvulsive [31–33], tranquilizing [34], and antiepileptic [35] activity. A 1,3-indanedione, miradon (anisindione, XIII, Fig.…”

Antimicrobial activity of 10-(diphenylmethylene)-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione derivatives

“…Many derivatives possess biological activity. They have antibacterial (Albuquerque et al 1999;Zentz et al 2002;Struga et al 2008a, b), anticonvulsive (Stratford and Curley 1983), hypnotic, sedative (Duarte et al 2006;Kozioł et al 2006), anxiolytic (Chilmończyk et al 1995), and antitumor properties (Di Pardo et al 2001;Kumar and Rajkumar 2006;Nakamura et al 2006). It is also known that compounds bearing short-amine fragment possess antibacterial and antifungal activity (Stefańska et al 2008).…”