Literature DB >> 21466221

Synthesis and separation of the enantiomers of the neuropeptide S receptor antagonist (9R/S)-3-oxo-1,1-diphenyl-tetrahydro-oxazolo[3,4-a]pyrazine-7-carboxylic acid 4-fluoro-benzylamide (SHA 68).

Claudio Trapella1, Michela Pela, Luisa Del Zoppo, Girolamo Calo, Valeria Camarda, Chiara Ruzza, Alberto Cavazzini, Valentina Costa, Valerio Bertolasi, Rainer K Reinscheid, Severo Salvadori, Remo Guerrini.   

Abstract

This study reports the synthesis, chromatographic separation, and pharmacological evaluation of the two enantiomers of the neuropeptide S receptor (NPSR) antagonist (9R/S)-3-oxo-1,1-diphenyl-tetrahydro-oxazolo[3,4-a]pyrazine-7-carboxylic acid 4-fluoro-benzylamide (SHA 68). The (9R)-3-oxo-1,1-diphenyl-tetrahydro-oxazolo[3,4-a]pyrazine-7-carboxylic acid 4-fluoro-benzylamide (compound 10) and (9S)-3-oxo-1,1-diphenyl-tetrahydro-oxazolo[3,4-a]pyrazine-7-carboxylic acid 4-fluoro-benzylamide (compound 10a) were synthesized and their purity assessed by chiral chromatography. The absolute configuration of the enantiomer 10 has been assigned from the crystal structure of the corresponding (S)-phenyl ethyl amine derivative 8. Calcium mobilization studies performed on cells expressing the recombinant NPSR demonstrated that compound 10 is the active enantiomer while the contribution of 10a to the NPSR antagonist properties of the racemic mixture is negligible.

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Year:  2011        PMID： 21466221      PMCID： PMC3095364          DOI： 10.1021/jm200138r

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  15 in total

1.  Further studies on the pharmacological profile of the neuropeptide S receptor antagonist SHA 68.

Authors:  Chiara Ruzza; Anna Rizzi; Claudio Trapella; Michela Pela'; Valeria Camarda; Valentina Ruggieri; Monica Filaferro; Carlo Cifani; Rainer K Reinscheid; Giovanni Vitale; Roberto Ciccocioppo; Severo Salvadori; Remo Guerrini; Girolamo Calo'
Journal:  Peptides       Date:  2010-02-19       Impact factor: 3.750

2.  Synthesis and pharmacological in vitro and in vivo profile of 3-oxo-1,1-diphenyl-tetrahydro-oxazolo[3,4-a]pyrazine-7-carboxylic acid 4-fluoro-benzylamide (SHA 68), a selective antagonist of the neuropeptide S receptor.

Authors:  Naoe Okamura; Stephen A Habay; Joanne Zeng; A Richard Chamberlin; Rainer K Reinscheid
Journal:  J Pharmacol Exp Ther       Date:  2008-03-12       Impact factor: 4.030

3.  Molecular modeling studies on the human neuropeptide S receptor and its antagonists.

Authors:  Diego Dal Ben; Ippolito Antonini; Michela Buccioni; Catia Lambertucci; Gabriella Marucci; Sauro Vittori; Rosaria Volpini; Gloria Cristalli
Journal:  ChemMedChem       Date:  2010-03-01       Impact factor: 3.466

4.  Pharmacological characterization of human and murine neuropeptide s receptor variants.

Authors:  Rainer K Reinscheid; Yan-Ling Xu; Naoe Okamura; Joanne Zeng; Shinjae Chung; Rama Pai; Zhiwei Wang; Olivier Civelli
Journal:  J Pharmacol Exp Ther       Date:  2005-09-06       Impact factor: 4.030

5.  Neuropeptide S: a neuropeptide promoting arousal and anxiolytic-like effects.

Authors:  Yan-Ling Xu; Rainer K Reinscheid; Salvador Huitron-Resendiz; Stewart D Clark; Zhiwei Wang; Steven H Lin; Fernando A Brucher; Joanne Zeng; Nga K Ly; Steven J Henriksen; Luis de Lecea; Olivier Civelli
Journal:  Neuron       Date:  2004-08-19       Impact factor: 17.173

6.  Neuropeptide S attenuates neuropathological, neurochemical and behavioral changes induced by the NMDA receptor antagonist MK-801.

Authors:  Naoe Okamura; Rainer K Reinscheid; Shintaro Ohgake; Masaomi Iyo; Kenji Hashimoto
Journal:  Neuropharmacology       Date:  2009-07-02       Impact factor: 5.250

7.  Highly stereoselective metal-free catalytic reduction of imines: an easy entry to enantiomerically pure amines and natural and unnatural alpha-amino esters.

Authors:  Stefania Guizzetti; Maurizio Benaglia; Sergio Rossi
Journal:  Org Lett       Date:  2009-07-02       Impact factor: 6.005

8.  Further studies at neuropeptide s position 5: discovery of novel neuropeptide S receptor antagonists.

Authors:  Remo Guerrini; Valeria Camarda; Claudio Trapella; Girolamo Caló; Anna Rizzi; Chiara Ruzza; Stella Fiorini; Erika Marzola; Rainer K Reinscheid; Domenico Regoli; Severo Salvadori
Journal:  J Med Chem       Date:  2009-07-09       Impact factor: 7.446

9.  In vitro and in vivo pharmacological characterization of the neuropeptide s receptor antagonist [D-Cys(tBu)5]neuropeptide S.

Authors:  Valeria Camarda; Anna Rizzi; Chiara Ruzza; Silvia Zucchini; Giuliano Marzola; Erika Marzola; Remo Guerrini; Severo Salvadori; Rainer K Reinscheid; Domenico Regoli; Girolamo Calò
Journal:  J Pharmacol Exp Ther       Date:  2008-10-29       Impact factor: 4.030

10.  Synthesis and biological activity of human neuropeptide S analogues modified in position 5: identification of potent and pure neuropeptide S receptor antagonists.

Authors:  Remo Guerrini; Valeria Camarda; Claudio Trapella; Girolamo Calò; Anna Rizzi; Chiara Ruzza; Stella Fiorini; Erika Marzola; Rainer K Reinscheid; Domenico Regoli; Severo Salvadori
Journal:  J Med Chem       Date:  2009-01-22       Impact factor: 7.446
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  8 in total

1.  Intranasally administered neuropeptide S (NPS) exerts anxiolytic effects following internalization into NPS receptor-expressing neurons.

Authors:  Irina A Ionescu; Julien Dine; Yi-Chun Yen; Dominik R Buell; Leonie Herrmann; Florian Holsboer; Matthias Eder; Rainer Landgraf; Ulrike Schmidt
Journal:  Neuropsychopharmacology       Date:  2012-01-25       Impact factor: 7.853

2.  Structure-activity relationship of imidazopyridinium analogues as antagonists of neuropeptide s receptor.

Authors:  Samarjit Patnaik; Juan J Marugan; Ke Liu; Wei Zheng; Noel Southall; Seameen J Dehdashti; Annika Thorsell; Markus Heilig; Lauren Bell; Michelle Zook; Bob Eskay; Kyle R Brimacombe; Christopher P Austin
Journal:  J Med Chem       Date:  2013-11-11       Impact factor: 7.446

3.  Identification of neuropeptide S antagonists: structure-activity relationship studies, X-ray crystallography, and in vivo evaluation.

Authors:  Carla Hassler; Yanan Zhang; Brian Gilmour; Tyler Graf; Timothy Fennell; Rodney Snyder; Jeffrey R Deschamps; Rainer K Reinscheid; Celia Garau; Scott P Runyon
Journal:  ACS Chem Neurosci       Date:  2014-07-11       Impact factor: 4.418

4.  A novel brain penetrant NPS receptor antagonist, NCGC00185684, blocks alcohol-induced ERK-phosphorylation in the central amygdala and decreases operant alcohol self-administration in rats.

Authors:  Annika Thorsell; Jenica D Tapocik; Ke Liu; Michelle Zook; Lauren Bell; Meghan Flanigan; Samarjit Patnaik; Juan Marugan; Ruslan Damadzic; Seameen J Dehdashti; Melanie L Schwandt; Noel Southall; Christopher P Austin; Robert Eskay; Roberto Ciccocioppo; Wei Zheng; Markus Heilig
Journal:  J Neurosci       Date:  2013-06-12       Impact factor: 6.167

Review 5.  Pharmacology, Physiology and Genetics of the Neuropeptide S System.

Authors:  Rainer K Reinscheid; Chiara Ruzza
Journal:  Pharmaceuticals (Basel)       Date:  2021-04-23

6.  Structure-Activity Relationship Studies on Oxazolo[3,4-a]pyrazine Derivatives Leading to the Discovery of a Novel Neuropeptide S Receptor Antagonist with Potent In Vivo Activity.

Authors:  Valentina Albanese; Chiara Ruzza; Erika Marzola; Tatiana Bernardi; Martina Fabbri; Anna Fantinati; Claudio Trapella; Rainer K Reinscheid; Federica Ferrari; Chiara Sturaro; Girolamo Calò; Giorgio Amendola; Sandro Cosconati; Salvatore Pacifico; Remo Guerrini; Delia Preti
Journal:  J Med Chem       Date:  2021-03-18       Impact factor: 7.446

7.  Identification of a role for the ventral hippocampus in neuropeptide S-elicited anxiolysis.

Authors:  Julien Dine; Irina A Ionescu; Jens Stepan; Yi-Chun Yen; Florian Holsboer; Rainer Landgraf; Matthias Eder; Ulrike Schmidt
Journal:  PLoS One       Date:  2013-03-28       Impact factor: 3.240

8.  Nasal application of neuropeptide S inhibits arthritis pain-related behaviors through an action in the amygdala.

Authors:  Georgina Medina; Guangchen Ji; Stéphanie Grégoire; Volker Neugebauer
Journal:  Mol Pain       Date:  2014-05-29       Impact factor: 3.395
  8 in total

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