Literature DB >> 17976996

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.

Emilie D Smith1, N Ariane Vinson, Desong Zhong, Bertold D Berrang, Jennifer L Catanzaro, James B Thomas, Hernán A Navarro, Brian P Gilmour, Jeffrey Deschamps, F Ivy Carroll.   

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.

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Year:  2007        PMID： 17976996      PMCID： PMC2323199          DOI： 10.1016/j.bmc.2007.10.023

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  15 in total

1.  Discovery of the first potent and selective small molecule opioid receptor-like (ORL1) antagonist: 1-[(3R,4R)-1-cyclooctylmethyl-3- hydroxymethyl-4-piperidyl]-3-ethyl-1, 3-dihydro-2H-benzimidazol-2-one (J-113397).

Authors:  H Kawamoto; S Ozaki; Y Itoh; M Miyaji; S Arai; H Nakashima; T Kato; H Ohta; Y Iwasawa
Journal:  J Med Chem       Date:  1999-12-16       Impact factor: 7.446

2.  Nociceptin/orphanin FQ microinjected into hippocampus impairs spatial learning in rats.

Authors:  J Sandin; J Georgieva; P A Schött; S O Ogren; L Terenius
Journal:  Eur J Neurosci       Date:  1997-01       Impact factor: 3.386

3.  Nociceptin stimulates locomotion and exploratory behaviour in mice.

Authors:  S Florin; C Suaudeau; J C Meunier; J Costentin
Journal:  Eur J Pharmacol       Date:  1996-12-12       Impact factor: 4.432

Review 4.  The opioid-receptor-like 1 (ORL-1) as a potential target for new analgesics.

Authors:  D Barlocco; G Cignarella; G A Giardina; L Toma
Journal:  Eur J Med Chem       Date:  2000-03       Impact factor: 6.514

5.  A new synthetic approach to 1-[(3R,4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidyl]-3-ethyl-1,3-dihydro-benzimidazol-2-one(J-113397), the first non-peptide ORL-1 receptor antagonist..

Authors:  C De Risi; G Piero Pollini; C Trapella; I Peretto; S Ronzoni; G A Giardina
Journal:  Bioorg Med Chem       Date:  2001-07       Impact factor: 3.641

Review 6.  Nociceptin/orphanin FQ peptide receptors: pharmacology and clinical implications.

Authors:  L-C Chiou; Y-Y Liao; P-C Fan; P-H Kuo; C-H Wang; C Riemer; E P Prinssen
Journal:  Curr Drug Targets       Date:  2007-01       Impact factor: 3.465

7.  Orphanin FQ is a functional anti-opioid peptide.

Authors:  J S Mogil; J E Grisel; R K Reinscheid; O Civelli; J K Belknap; D K Grandy
Journal:  Neuroscience       Date:  1996-11       Impact factor: 3.590

8.  Nociceptin/orphanin FQ modulates spatial learning via ORL-1 receptors in the dorsal hippocampus of the rat.

Authors:  Johan Sandin; Sven O Ogren; Lars Terenius
Journal:  Brain Res       Date:  2004-02-06       Impact factor: 3.252

9.  ORL1, a novel member of the opioid receptor family. Cloning, functional expression and localization.

Authors:  C Mollereau; M Parmentier; P Mailleux; J L Butour; C Moisand; P Chalon; D Caput; G Vassart; J C Meunier
Journal:  FEBS Lett       Date:  1994-03-14       Impact factor: 4.124

10.  Isolation and structure of the endogenous agonist of opioid receptor-like ORL1 receptor.

Authors:  J C Meunier; C Mollereau; L Toll; C Suaudeau; C Moisand; P Alvinerie; J L Butour; J C Guillemot; P Ferrara; B Monsarrat
Journal:  Nature       Date:  1995-10-12       Impact factor: 49.962
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  3 in total

1.  In silico study of the structurally similar ORL1 receptor agonist and antagonist pairs reveal possible mechanism of receptor activation.

Authors:  Milan Senćanski; Ljiljana Dosen-Mićović
Journal:  Protein J       Date:  2014-06       Impact factor: 2.371

2.  Ammonium [(1S)-(endo,anti)]-(-)-3-bromo-camphor-8-sulfonate.

Authors:  Muhammad Athar Abbasi; Mehmet Akkurt; Muhammad Jahangir; Seik Weng Ng; Islam Ullah Khan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-06-18

3.  Lansoprazole-Based Colorimetric Chemosensor for Efficient Binding and Sensing of Carbonate Ion: Spectroscopy and DFT Studies.

Authors:  Mahdieh Darroudi; Ghodsi Mohammadi Ziarani; Shahriyar Bahar; Jahan B Ghasemi; Alireza Badiei
Journal:  Front Chem       Date:  2021-02-02       Impact factor: 5.221
  3 in total

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