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  • Synthesis and biological evaluation of some 6-arylamidomorphines as analogues of morphine-6-glucuronide.

Synthesis and biological evaluation of some 6-arylamidomorphines as analogues of morphine-6-glucuronide.

Bioorganic & medicinal chemistry (2004-10-23)
James M Macdougall, Xiao-Dong Zhang, Willma E Polgar, Taline V Khroyan, Lawrence Toll, John R Cashman
ABSTRACT

A series of 6-beta-arylamidomorphines was synthesized and biologically evaluated. Various aryl substituents were introduced into the arylamidomorphines to examine substituent structure-activity relationships. Competition binding assays showed that compounds 10a-h bound to the mu opioid receptor with high affinity (0.2-0.6 nM). Functional assays showed that compounds 10a-h acted as full mu opioid receptor agonists. The ED(50) of compound 10e.HCl as an analgesic was 12.6 mg/kg in the tail flick latency test in the rat.

MATERIALS
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Brand
Product Description

Sigma-Aldrich
2-Thiopheneacetyl chloride, 98%