Synthesis and evaluation of 3-aminopropionyl substituted fentanyl analogues for opioid activity

被引：27

作者：

Petrov, Ravil R.

Vardanyan, Ruben S.

Lee, Yeon S.

Ma, Shou-wu

Davis, Peg

Begay, Lucinda J.

Lai, Josephine Y.

Porreca, Frank

Hruby, Victor J. ^{[1
]}

机构：

[1] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA

[2] Univ Arizona, Dept Pharmacol, Tucson, AZ 85721 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2006年 / 16卷 / 18期

关键词：

fentanyl derivatives; opioid agonists; enkephalin analogue; PHARMACOLOGICAL EVALUATION; ANALGESIC ACTIVITY; RECEPTOR; LIGANDS; DERIVATIVES; AFFINITY; AGONIST; POTENT; ANTAGONISTS; PEPTIDE;

D O I：

10.1016/j.bmcl.2006.06.040

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

An enkephalin analogue coupled to 'aminofentanyl' has been synthesized and tested for biological activities at the mu and delta opioid receptors. Aminofentanyl which represents a structural derivative of fentanyl has been synthesized by acylation of 1-(2-phenethyl)-4-(N-anilino)piperidine with phthaloyl protected beta-alaninyl chloride in the presence of DIPEA, followed by deprotection with hydrazine hydrate. Aminofentanyl has also been successfully acylated with ethyl isocyanate, various acid anhydrides, to further investigate structure-activity relationships of these new fentanyl derivatives. Among the new derivatives compound 7 which carries a Tyr-D-Ala-Gly-Phe opioid message sequence showed good opioid affinity (1 nM at both delta and mu opioid receptors) and bioactivity (34.9 nM in MVD and 42 nM in GPI/LMMP bioassays). (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：4946 / 4950

页数：5

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