[Intramolecular aromatic alkylation. 28. Synthesis and pharmacological testing of homologized and hydroxylated 3,4-dihydro-1'-methylspiro[naphthalin-1(2H),4'-piperidine].
The compounds 4, 8, and 10, prepared by standard methods, are converted to the phenylpyridylakanes 9; their methoiodides 11 are reduced to yield the tetrahydropyridines 12. Whereas the cyclisation of 12a gives the isomers 1f and 1g, 12b furnishes only the isomer 1i or 1k, respectively. H3PO4 is found to be more suitable than HBr to cyclize 12c and 12d to the homologues 1l and 1m. Treatment of 12c and 12d affords the bromides 13a and 13b by HBr-addition, which are isolated for the first time. Compounds 1l, 1b, 1c, and 1a exhibit a notable activity in the writhing test, whereas the hydroxylated derivatives 1h, 1e, and 1f are definitely less active. The homologue 1m is inactive.
Reimann
E
E
Institut für Pharmazie und Lebensmittelchemie, Universität München.
Speckbacher
J
J
Schünemann
J
J
D000700:Analgesics / Q000138:chemical synthesis*; D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D051379:Mice; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000494:pharmacology; D010880:Piperidines / Q000138:chemical synthesis* / Q000494:pharmacology; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000494:pharmacology
D000700:Analgesics; D009281:Naphthalenes; D010880:Piperidines; D013141:Spiro Compounds
Synthese und pharmakologische Prüfung homologer und hydroxylierter 3,4-Dihydro-1'-methylspiro[naphthalin-1(2H),4'-piperidine].