• Journal Article

A new synthesis of the ORL-1 antagonist 1-[(3R,4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidinyl]-3-ethyl-1,3-dihydro- 2H-benzimidazol-2-one (J-113397) and activity in a calcium mobilization assay

Citation

Smith, E. D., Ariane, V. N., Zhong, D., Berrang, B., Catanzaro, J., Thomas, J., ... Carroll, F. (2008). A new synthesis of the ORL-1 antagonist 1-[(3R,4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidinyl]-3-ethyl-1,3-dihydro- 2H-benzimidazol-2-one (J-113397) and activity in a calcium mobilization assay. Bioorganic and Medicinal Chemistry, 16(2), 822-829.

Abstract

A new chiral synthesis of the ORL-1 antagonist 1-[(3R,4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidinyl]-3-ethyl-1,3-dihydro- 2H-benzimidazol-2-one (2, J-113397) was developed. J-113397 has a K(e)=0.85nM in an ORL-1 calcium mobilization assay and is 89-, 887-, and 227-fold selective for the ORL-1 receptor relative to the mu, delta, and kappa opioid receptors