Novel N1-(benzyl)cinnamamidine derived NR2B subtype-selective NMDA receptor antagonists

Glutamate Receptor Ion Channels: Structure, Regulation, and Function

“…Similar to Zn 2ϩ binding to the ATD of GluN2A (see section VI.E), ifenprodil increases the potency of proton inhibition of NMDA receptors Mott et al, 1998). Rich pharmacology exists for this site, with nearly a dozen structural classes described, including oxamides (Barta-Szalai et al, 2004), 4-(3,4-dihydro-1H-isoquinolin-2-yl)-quinolines (Bü ttelmann et al, 2003), benzamidines (Claiborne et al, 2003), 5-substituted benzimidazoles (McCauley et al, 2004), indole-2-carboxamides (Borza et al, 2006(Borza et al, , 2007, benzyl cinnamamidines (Tamiz et al, 1999;Curtis et al, 2003), and other biaryl analogs (Tamiz et al, 1998;Wright et al, 2000;Tahirovic et al, 2008;Mosley et al, 2009). …”

7-Amino-2-phenylpyrazolo[4,3-d]pyrimidine derivatives: Structural investigations at the 5-position to target human A1 and A2A adenosine receptors. Molecular modeling and pharmacological studies

“…The methoxy-substituted pyrazolopyrimidines 6e8 were reacted with boron tribromide to be transformed into the corresponding hydroxy-derivatives 16e18. To synthesize the 5-(E)-cynnamyl-derivatives 20e21 (Scheme 2), the pyrazole-3-carbonitrile 34 was cyclized with the (E) ethyl cinnamidate and (E) 4-methoxycinnamidate hydrochlorides, 35 [42] and 36 [43], respectively. Compound 21 was demethylated to give the corresponding hydroxy-derivative 22.…”

Simple Preparation of New Potential Bioactive Nitrogen-Containing Molecules and Their Spectroscopy Analysis

“…Among these important and interesting class of organic molecules: N-benzylcinnamides and Nphenylcinnamides have been always the focus of attention of organic, bioorganic and medicinal chemists due to their many useful synthetic applications (Takasu et al, 2003;Bernini et al, 2006;Nair et al, 2007) as well as their diverse (bio)chemical properties (Curtis et al, 2003;Tamiz et al, 1999;Lewis et al, 1991). Moreover, N-amide cinnamic acid derivatives are frequently presented in the nature (Mbaze et al, 2009;Vasques et al, 2002).…”