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Analogs of the Muscarinic Agent 2'‑Methylspiro(1‑azabicyclo[2.2.2]octane)­‑3,4'‑[1,3]dioxolane (AF30): Synthesis and Pharmacology
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
KABI PHARM AB, DEPT RECEPTOR PHARMACOL UROL GYNAECOL, S-11287 STOCKHOLM, SWEDEN.
KABI PHARM AB, DEPT RECEPTOR PHARMACOL UROL GYNAECOL, S-11287 STOCKHOLM, SWEDEN.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
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1992 (English)In: Journal of Medicinal Chemistry, ISSN 0022-2623, E-ISSN 1520-4804, Vol. 35, no 9, 1541-1550 p.Article in journal (Refereed) Published
Abstract [en]

A number of tetrahydrofuran analogues of 2'-methylspiro[1-azabicyclo[2.2.2]octane-3,4'-[1,3]dioxolane] ( 1) have been prepared with the aim to obtain information about the relative importance of each of the oxygens in 1 for efficacy and for selectivity. In addition, the dimethyl and deamethyl doguea of 1 &re prepared. The new compounds were compared to cis- and trans-1 with regard to their ability to displace (-)-[3H]-3-quinuclidinyl benzilate ((-)-[3H]QNB) from muscarinic receptors in cerebral cortex, heart, parotid gland, and urinary bladder from  guinea pigs. Functioinal studies were made on isolated guinea pig bladder and ileum. The new compounds exhibited both lower affmity and efficacy thancis-1.Aconformational studywasperformed,and the effects of steric and electronic factors on the biological activity of the compounds are discussed.

Place, publisher, year, edition, pages
1992. Vol. 35, no 9, 1541-1550 p.
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Natural Sciences
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URN: urn:nbn:se:uu:diva-140720DOI: 10.1021/jm00087a007OAI: oai:DiVA.org:uu-140720DiVA: diva2:384258
Available from: 2011-01-08 Created: 2011-01-08 Last updated: 2017-12-11Bibliographically approved

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Gogoll, Adolf

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