Identification of potent phenyl imidazoles as opioid receptor agonists

Using previously reported opioid receptor (OR) agonist analogs 4a– c as starting points, the structure–activity relationship (SAR) for their related series has been further refined. This SAR study has led to the identification of 2,6-di-Me-Tyr (DMT) analogs 4h and 4j as the most potent OR agonist wi...

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Veröffentlicht in:	Bioorganic & medicinal chemistry letters 2006-05, Vol.16 (9), p.2505-2508
Hauptverfasser:	Breslin, Henry J., Cai, Chaozhong, Miskowski, Tamara A., Coutinho, Santosh V., Zhang, Sui-Po, Hornby, Pamela, He, Wei
Format:	Artikel
Sprache:	eng
Schlagworte:	2,6-Di-Me-4-carboxamido-Phe 2,6-Dimethyl-Tyr 4-(Aminocarbonyl)-2,6-dimethyl-Phe Biological and medical sciences DMT Imidazoles - chemical synthesis Imidazoles - chemistry Imidazoles - pharmacology Medical sciences Molecular Structure Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Opioid receptor agonist Opioid receptor ligands Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems Pharmacology. Drug treatments Phenyl imidazole Receptors, Opioid - agonists Stereoisomerism Structure-Activity Relationship
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Zusammenfassung:	Using previously reported opioid receptor (OR) agonist analogs 4a– c as starting points, the structure–activity relationship (SAR) for their related series has been further refined. This SAR study has led to the identification of 2,6-di-Me-Tyr (DMT) analogs 4h and 4j as the most potent OR agonist within the series. In addition, it was discovered that 4-(aminocarbonyl)-2,6-dimethyl-Phe is a reasonable bioisostere surrogate for the DMT moiety, as supported by the OR activities of compounds 4x and 4y.
ISSN:	0960-894X 1464-3405
DOI:	10.1016/j.bmcl.2006.01.082