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Bioorg Med Chem Lett. 2009 May 15;19(10):2792-5. doi: 10.1016/j.bmcl.2009.03.099. Epub 2009 Mar 26.

Design and synthesis of novel delta opioid receptor agonists and their pharmacologies.

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Department of Medicinal Chemistry, Kitasato University, Shirokane, Minato-ku, Tokyo, Japan.


We re-examined the accessory site of the 4,5-epoxymorphinan skeleton by camdas conformational analysis in an effort to deign novel delta opioid receptor antagonists. We synthesized three novel compounds (SN-11, 23 and 28) with a 10-methylene bridge and without a 4,5-epoxy ring. Among them, compounds SN-23 (17-isobutyl derivative) and SN-28 (17-methyl derivative) showed very strong agonist activity (over 10 times more than TAN-67). SN-28 also showed high delta selectivity. The delta agonist activity of SN-23 was weaker than that of SN-28, but in terms of the delta selectivity, SN-23 was higher than that of SN-28. These unexpected results indicated that the 4,5-epoxy ring, but not the 10-methylene bridge, was an accessory site in delta opioid receptor agonists.

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