Sökning: onr:"swepub:oai:DiVA.org:kth-317903" >
New nepenthone and ...
New nepenthone and thevinone derivatives
-
Marton, J. (författare)
-
Simon, C. (författare)
-
Hosztafi, S. (författare)
-
visa fler...
-
- Szabó, Zoltan, Associate professor (författare)
- Alkaloida Chemical Company Ltd., Tiszavasvári, H-4440, P.O. Box 1, Hungary
-
Márki, A. (författare)
-
Borsodi, A. (författare)
-
Makleit, S. (författare)
-
visa färre...
-
Alkaloida Chemical Company Ltd, Tiszavasvári, H-4440, P.O. Box 1, Hungary (creator_code:org_t)
- Elsevier BV, 1997
- 1997
- Engelska.
-
Ingår i: Bioorganic & Medicinal Chemistry. - : Elsevier BV. - 0968-0896 .- 1464-3391. ; 5:2, s. 369-382
- Relaterad länk:
-
https://urn.kb.se/re...
-
visa fler...
-
https://doi.org/10.1...
-
visa färre...
Abstract
Ämnesord
Stäng
- The diastereoselective reaction of thevinone (2a) and nepenthone (2c) and their dihydro derivatives (2b and d) with Grignard reagents afforded new N-substituted (20S)- and (20R)-phenyI-6,14-ethenomorphinan derivatives (6a-y). The Grignard reaction of the N-substituted-N-demethyl derivatives 4a-f and 4m-r with methylmagnesium iodide resulted in the (20R)-phenyl tertiary alcohols 5a-f and 5m-r, respectively, but the conversion of 4g-l and that of the N-substituted-dihydrothevinone derivatives with phenylmagnesium bromide afforded the (20S)-phenyl derivatives 5g-l and 5s-y, respectively. The N-cyclopropylmethyl-, N-β-phenylethyl-, and N-propyl derivatives were prepared by the 3-O-demethylation of compounds 5. For the synthesis of the N-allyl-, N-dimethylallyl-, and N-propargyl compounds 2a-d were reacted with the corresponding Grignard reagent, and treatment of the products with cyanogen bromide gave the cyanamides 8a-d. These latter compounds were transformed into 10a,b,d, whose alkylation led to the target derivatives 6d-f, j-l, p-r, and w-y. The biochemical investigation of these substances showed that the affinities to the δ-opioid receptors were high, but the selectivity was low. Tn two cases (6c and 11d) a μ-opioid receptor specificity was observed.
Ämnesord
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
Publikations- och innehållstyp
- ref (ämneskategori)
- art (ämneskategori)
Hitta via bibliotek
Till lärosätets databas