Conformationally restricted analogs of histamine H1 receptor antagonists: trans and cis-1-benzyl-3-dimethylamino-6-phenylpiperidine.
The syntheses of trans- and cis-1-benzyl-3-dimethylamino-6-phenylpiperidine (1 and 2) are described. Compounds 1 and 2 were found to be inhibitors to histamine, acetylcholine, and barium chloride induced contractions of the isolated guinea pig ileum. Compounds 1 and 2 do not exhibit appreciable stereoselectivity in their ability to inhibit smooth muscle contractions. The cis compound 2 is a more effective inhibitor of histamine N-methyltransferase than the trans isomer 1.
D000109:Acetylcholine / Q000494:pharmacology; D000818:Animals; D001464:Barium / Q000494:pharmacology; D004123:Dimethylamines / Q000138:chemical synthesis / Q000494:pharmacology; D006168:Guinea Pigs; D006632:Histamine / Q000494:pharmacology; D006634:Histamine H1 Antagonists / Q000138:chemical synthesis*; D006637:Histamine N-Methyltransferase / Q000037:antagonists & inhibitors; D007082:Ileum / Q000187:drug effects; D066298:In Vitro Techniques; D008968:Molecular Conformation; D009119:Muscle Contraction / Q000187:drug effects; D009130:Muscle, Smooth / Q000187:drug effects; D010880:Piperidines / Q000138:chemical synthesis* / Q000494:pharmacology; D011955:Receptors, Drug; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D004123:Dimethylamines; D006634:Histamine H1 Antagonists; D010880:Piperidines; D011955:Receptors, Drug; D001464:Barium; D006632:Histamine; D006637:Histamine N-Methyltransferase; D000109:Acetylcholine