0000000000177593
AUTHOR
Sigurd Elz
Racemattrennung, Kristallstruktur und histaminartige Wirkung von 4-[1-(2-Aminoethylthio)ethyl]-5-methylimidazol
Es wird die Racemattrennung von 4-[1-(2-Aminoethylthio)ethyl]-5-methylimidazol (1) mittels optisch aktiver Di-O-(p-toluoyl)weinsaure sowie die histaminartige Wirksamkeit der Enantiomeren beschrieben. Von (+)-1 · 2HCl · H2O wurde die Kristallstruktur bestimmt und bis zu einem R-Wert von 0.0483 verfeinert. Danach ist (+)-1R-konfiguriert. Von den beiden Enantiomeren besitzt nur (S)-(−)-1 H1-agonistische Aktivitat. Resolution, Crystal Structure, and Histamine-like Activity of 4-[1-(2-Aminoethylthio)ethyl]-5-methylimidazole The resolution of racemic 4-[1-(2-aminoethylthio)ethyl]-5-methylimidazole (1) using optically active Di-O-(P-toluoyl)tartaric acid as well as the histamine-like activity of t…
Histaprodifens: synthesis, pharmacological in vitro evaluation, and molecular modeling of a new class of highly active and selective histamine H(1)-receptor agonists.
A new class of histamine analogues characterized by a 3, 3-diphenylpropyl substituent at the 2-position of the imidazole nucleus has been prepared outgoing from 4,4-diphenylbutyronitrile (4b) via cyclization of the corresponding methyl imidate 5b with 2-oxo-4-phthalimido-1-butyl acetate or 2-oxo-1,4-butandiol in liquid ammonia, followed by standard reactions. The title compounds displayed partial agonism on contractile H(1) receptors of the guinea-pig ileum and endothelium-denuded aorta, respectively, except 10 (histaprodifen; 2-[2-(3, 3-diphenylpropyl)-1H-imidazol-4-yl]ethanamine) which was a full agonist in the ileum assay. While 10 was equipotent with histamine (1), methylhistaprodifen (…
Darstellung und H2-agonistische Aktivität alkylsubstituierter 3-(Imidazol-4-yl)propylguanidine Synthesis and H2-Agonistic Activity of Alkyl-3-(imidazole-4-yl)propylguanidines
Derivate des 3-(Imidazol-4-yl)propylguanidins mit einem Methyl- oder einem 2-(Ethylthio)ethyl-Substituenten2) an der Guanidin-Gruppe weisen am H2-Rezeptor des Meerschweinchenvorhofs nur 10–20% der Histaminaktivitat auf. Dagegen fuhrt die Substitution mit der H2-affinen 2-[(5-Methylimidazol-4-yl) methylthio]ethyl-Gruppierung zu Impromidin, einem hochpotenten H2-Agonisten.
Histamine analogues. 32nd communication: synthesis and pharmacology of sopromidine, a potent and stereoselective isomer of the achiral H2-agonist impromidine
Abstract Synthesis and pharmacology of sopromidine (( R )-7) and ( S )- 7 , 2 position isomers of impromidine derived from the enantiomeric α-methylhistamines, are reported. The enantiomers of 7 show high stereoselectivity at the atrial H 2 -receptor of the guinea-pig. ( R )- 7 is revealed to be a full H 2 -agonist with 7.4-fold potency relative to histamine, while ( S )- 7 is a competitive H 2 -antagonist.
Darstellung, Kristallstruktur und Wirkung von 2-Methyl-3-(4-oxo-3-phenyl-thiazolidin-2-ylidenamino)-4-(3H)-chinazolinon
Quinazolinones. 1. Preparation, crystal structure and action of 2-methyl-3-(4-oxo-3-phenyl-thiazolidine-2-ylidenamino)-4-(3H)- quinazolinone.
S-Methylisothioharnstoffe, Bausteine kettenverzweigter Cimetidin-DerivateS-Methylisothioureas, Synthons for Chain-Branched Cimetidine Derivates
A partir de S,S-dimethyl N-cyano dithiocarbonimidate et d'amino-2' alkyl (ramifie) thiomethyl-4 methyl-5 imidazoles (A), synthese des derives de A substitues sur l'amino-2' par [cyanoimino methylthiomethyle]