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

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• 作者：Emilie D. Smith ; N. Ariane Vinson ; Desong Zhong ; Bertold D. Berrang ; Jennifer L. Catanzaro ; James B. Thomas ; Herná ; n A. Navarro ; Brian P. Gilmour ; Jeffrey Deschamps ; F. Ivy Carroll
• 关键词：J-113397 ; ORL-1 antagonist ; Chiral synthesis ; NOP
• 刊名：Bioorganic and Medicinal Chemistry
• 出版年：2008
• 出版时间：15 January 2008
• 年：2008
• 卷：16
• 期：2
• 页码：822-829
• 全文大小：266 K

文摘

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 (<strong>2strong>, J-113397) was developed. J-113397 has a K_e = 0.85 nM in an ORL-1 calcium mobilization assay and is 89-, 887-, and 227-fold selective for the ORL-1 receptor relative to the μ, δ, and κ opioid receptors.