TY - JOUR
T1 - Synthesis and Evaluation of 1- and 2-Substituted Fentanyl Analogues for Opioid Activity
AU - Essawi, Mohamed Y.H.
AU - Portoghese, Philip S.
PY - 1983/3
Y1 - 1983/3
N2 - We synthesized fentanyl analogues that possess key groups common to the opioid peptides to investigate whether or not these two classes of compounds interact with common subsites on opioid receptors. The design of the analogues was based on the possibility of structural analogy between the two aromatic rings of fentanyl and the Tyr1 and Phe4 residues of the opioid peptides. The synthesized compounds showed very weak or no opioid activity as tested in the electrically stimulated longitudinal muscle of the guinea pig ileum or mouse vas deferens preparations. These results, together with those of reported studies, suggest that fentanyl and the opioid peptides interact with different subsites on either μ or δ receptors. Studies using the irreversible μ opioid receptor antagonist, β-funaltrexamine, indicate that fentanyl interacts preferentially with μ opioid receptors.
AB - We synthesized fentanyl analogues that possess key groups common to the opioid peptides to investigate whether or not these two classes of compounds interact with common subsites on opioid receptors. The design of the analogues was based on the possibility of structural analogy between the two aromatic rings of fentanyl and the Tyr1 and Phe4 residues of the opioid peptides. The synthesized compounds showed very weak or no opioid activity as tested in the electrically stimulated longitudinal muscle of the guinea pig ileum or mouse vas deferens preparations. These results, together with those of reported studies, suggest that fentanyl and the opioid peptides interact with different subsites on either μ or δ receptors. Studies using the irreversible μ opioid receptor antagonist, β-funaltrexamine, indicate that fentanyl interacts preferentially with μ opioid receptors.
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U2 - 10.1021/jm00357a007
DO - 10.1021/jm00357a007
M3 - Article
C2 - 6827557
AN - SCOPUS:0020660612
SN - 0022-2623
VL - 26
SP - 348
EP - 352
JO - Journal of medicinal chemistry
JF - Journal of medicinal chemistry
IS - 3
ER -