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Predicate | Object |
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
10
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pubmed:dateCreated |
1996-7-18
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pubmed:abstractText |
Several 8-amino-5,9-methanobenzocyclooctenes have been prepared by asymmetric organic synthesis techniques. Opioid receptor affinity studies have revealed the virtual absence of enantioselectivity for receptor binding, particularly at the mu-receptor, for the (+)-3a-f and the (-)-3a-f series. It is noteworthy that inversion of configuration at the nitrogen-bearing carbon atom [5S,8S,9S)-8-amino-3-hydroxy-5, 9-methano-9-(methoxymethyl)-5-methylbenzocyclooctene, (+)-3a vs (5S,8S,9R)-8-amino-3-hydroxy-5, 9-methano-9-(methoxymethyl)-5-methylbenzocyclooctene, (dl)-22] resulted in a > 10-fold increase in kappa-receptor affinity. Antinociceptive studies demonstrated that (dl)-22 was a full kappa-agonist while (+)-3a and (-)-3a did not possess kappa-activity. Although both (dl)-22 and (+)-3a/(-)-3a had high affinity for the mu-receptor, these compounds did not act as high-affinity agonists or antagonists at this receptor.
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pubmed:grant | |
pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical | |
pubmed:status |
MEDLINE
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pubmed:month |
May
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pubmed:issn |
0022-2623
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:day |
10
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pubmed:volume |
39
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
1956-66
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pubmed:dateRevised |
2007-11-14
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pubmed:meshHeading |
pubmed-meshheading:8642554-Alkaloids,
pubmed-meshheading:8642554-Analgesics, Opioid,
pubmed-meshheading:8642554-Animals,
pubmed-meshheading:8642554-Bridged Compounds,
pubmed-meshheading:8642554-Magnetic Resonance Spectroscopy,
pubmed-meshheading:8642554-Male,
pubmed-meshheading:8642554-Mass Spectrometry,
pubmed-meshheading:8642554-Mice,
pubmed-meshheading:8642554-Mice, Inbred ICR,
pubmed-meshheading:8642554-Molecular Structure,
pubmed-meshheading:8642554-Receptors, Opioid
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pubmed:year |
1996
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pubmed:articleTitle |
Asymmetric syntheses, opioid receptor affinities, and antinociceptive effects of 8-amino-5,9-methanobenzocyclooctenes, a new class of structural analogues of the morphine alkaloids.
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pubmed:affiliation |
Department of Chemistry, Rensselaer Polytechnic Institute, Troy, New York 12180-3590, USA.
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pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, P.H.S.,
Research Support, Non-U.S. Gov't
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