Literature DB >> 26985297

Discovery and Characterization of 2-Aminooxazolines as Highly Potent, Selective, and Orally Active TAAR1 Agonists.

Guido Galley1, Angélica Beurier1, Guillaume Décoret1, Annick Goergler1, Roman Hutter1, Susanne Mohr1, Axel Pähler1, Philipp Schmid1, Dietrich Türck1, Robert Unger1, Katrin Groebke Zbinden1, Marius C Hoener1, Roger D Norcross1.   

Abstract

2-Aminooxazolines were discovered as a novel structural class of TAAR1 ligands. Starting from a known adrenergic compound 1, structural modifications were made to obtain highly potent and selective TAAR1 ligands such as 12 (RO5166017), 18 (RO5256390), 36 (RO5203648), and 48 (RO5263397). These compounds exhibit drug-like physicochemical properties, have good oral bioavailability, and display in vivo activity in a variety of animal models relevant for psychiatric diseases and addiction.

Entities:  

Keywords:  2-aminooxazoline; SAR; TAAR1 agonist; schizophrenia

Year:  2015        PMID： 26985297      PMCID： PMC4753552          DOI： 10.1021/acsmedchemlett.5b00449

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  21 in total

1.  A new perspective for schizophrenia: TAAR1 agonists reveal antipsychotic- and antidepressant-like activity, improve cognition and control body weight.

Authors:  F G Revel; J-L Moreau; B Pouzet; R Mory; A Bradaia; D Buchy; V Metzler; S Chaboz; K Groebke Zbinden; G Galley; R D Norcross; D Tuerck; A Bruns; S R Morairty; T S Kilduff; T L Wallace; C Risterucci; J G Wettstein; M C Hoener
Journal:  Mol Psychiatry       Date:  2012-05-29       Impact factor: 15.992

2.  Risk assessment and mitigation strategies for reactive metabolites in drug discovery and development.

Authors:  Richard A Thompson; Emre M Isin; Yan Li; Richard Weaver; Lars Weidolf; Ian Wilson; Alf Claesson; Ken Page; Hugues Dolgos; J Gerry Kenna
Journal:  Chem Biol Interact       Date:  2010-11-11       Impact factor: 5.192

3.  Selective activation of the trace amine-associated receptor 1 decreases cocaine's reinforcing efficacy and prevents cocaine-induced changes in brain reward thresholds.

Authors:  Yue Pei; Patrick Mortas; Marius C Hoener; Juan J Canales
Journal:  Prog Neuropsychopharmacol Biol Psychiatry       Date:  2015-06-03       Impact factor: 5.067

4.  Taar1-mediated modulation of presynaptic dopaminergic neurotransmission: role of D2 dopamine autoreceptors.

Authors:  D Leo; L Mus; S Espinoza; M C Hoener; T D Sotnikova; R R Gainetdinov
Journal:  Neuropharmacology       Date:  2014-02-22       Impact factor: 5.250

5.  Trace amine-associated receptor 1 partial agonism reveals novel paradigm for neuropsychiatric therapeutics.

Authors:  Florent G Revel; Jean-Luc Moreau; Raul R Gainetdinov; Antonio Ferragud; Clara Velázquez-Sánchez; Tatyana D Sotnikova; Stephen R Morairty; Anja Harmeier; Katrin Groebke Zbinden; Roger D Norcross; Amyaouch Bradaia; Thomas S Kilduff; Barbara Biemans; Bruno Pouzet; Marc G Caron; Juan J Canales; Tanya L Wallace; Joseph G Wettstein; Marius C Hoener
Journal:  Biol Psychiatry       Date:  2012-06-16       Impact factor: 13.382

6.  Novel mechanism for dehalogenation and glutathione conjugation of dihalogenated anilines in human liver microsomes: evidence for ipso glutathione addition.

Authors:  Chenghong Zhang; Jane R Kenny; Hoa Le; Alan Deese; Kevin A Ford; Luke K Lightning; Peter W Fan; James P Driscoll; Jason S Halladay; Cornelis E C A Hop; S Cyrus Khojasteh
Journal:  Chem Res Toxicol       Date:  2011-09-25       Impact factor: 3.739

Review 7.  In-vivo pharmacology of Trace-Amine Associated Receptor 1.

Authors:  Vincent M Lam; Stefano Espinoza; Andrey S Gerasimov; Raul R Gainetdinov; Ali Salahpour
Journal:  Eur J Pharmacol       Date:  2015-06-17       Impact factor: 4.432

8.  S18616, a highly potent, spiroimidazoline agonist at alpha(2)-adrenoceptors: I. Receptor profile, antinociceptive and hypothermic actions in comparison with dexmedetomidine and clonidine.

Authors:  M J Millan; A Dekeyne; A Newman-Tancredi; D Cussac; V Audinot; G Milligan; D Duqueyroix; S Girardon; J Mullot; J A Boutin; J P Nicolas; A Renouard-Try; J M Lacoste; A Cordi
Journal:  J Pharmacol Exp Ther       Date:  2000-12       Impact factor: 4.030

Review 9.  N-glucuronidation of drugs and other xenobiotics by human and animal UDP-glucuronosyltransferases.

Authors:  Sanna Kaivosaari; Moshe Finel; Mikko Koskinen
Journal:  Xenobiotica       Date:  2011-03-24       Impact factor: 1.908

10.  Optimisation of imidazole compounds as selective TAAR1 agonists: discovery of RO5073012.

Authors:  Guido Galley; Henri Stalder; Annick Goergler; Marius C Hoener; Roger D Norcross
Journal:  Bioorg Med Chem Lett       Date:  2012-06-23       Impact factor: 2.823
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  9 in total

1.  Trace amine-associated receptor 1 (TAAR1) promotes anti-diabetic signaling in insulin-secreting cells.

Authors:  Emily S Michael; Lidija Covic; Athan Kuliopulos
Journal:  J Biol Chem       Date:  2019-01-22       Impact factor: 5.157

Review 2.  Binding of SEP-363856 within TAAR1 and the 5HT1A receptor: implications for the design of novel antipsychotic drugs.

Authors:  Pramod C Nair; John O Miners; Ross A McKinnon; Christopher J Langmead; Karen J Gregory; David Copolov; Sherry Kit Wa Chan; Tarun Bastiampillai
Journal:  Mol Psychiatry       Date:  2021-08-10       Impact factor: 15.992

Review 3.  Progress in mechanistically novel treatments for schizophrenia.

Authors:  James Neef; Daniel S Palacios
Journal:  RSC Med Chem       Date:  2021-06-29

Review 4.  DARK Classics in Chemical Neuroscience: Aminorex Analogues.

Authors:  Julian Maier; Felix P Mayer; Simon D Brandt; Harald H Sitte
Journal:  ACS Chem Neurosci       Date:  2018-10-05       Impact factor: 5.780

5.  Pharmacological characterization of a high-affinity p-tyramine transporter in rat brain synaptosomes.

Authors:  Mark D Berry; Shannon Hart; Anthony R Pryor; Samantha Hunter; Danielle Gardiner
Journal:  Sci Rep       Date:  2016-11-30       Impact factor: 4.379

6.  Behavioral Effects of a Potential Novel TAAR1 Antagonist.

Authors:  Vincent M Lam; Catharine A Mielnik; Corey Baimel; Pieter Beerepoot; Stefano Espinoza; Ilya Sukhanov; Wendy Horsfall; Raul R Gainetdinov; Stephanie L Borgland; Amy J Ramsey; Ali Salahpour
Journal:  Front Pharmacol       Date:  2018-09-04       Impact factor: 5.810

7.  Discovery and In Vivo Efficacy of Trace Amine-Associated Receptor 1 (TAAR1) Agonist 4-(2-Aminoethyl)-N-(3,5-dimethylphenyl)piperidine-1-carboxamide Hydrochloride (AP163) for the Treatment of Psychotic Disorders.

Authors:  Mikhail Krasavin; Anatoly A Peshkov; Alexey Lukin; Kristina Komarova; Lyubov Vinogradova; Daria Smirnova; Evgeny V Kanov; Savelii R Kuvarzin; Ramilya Z Murtazina; Evgeniya V Efimova; Maxim Gureev; Kirill Onokhin; Konstantin Zakharov; Raul R Gainetdinov
Journal:  Int J Mol Sci       Date:  2022-09-30       Impact factor: 6.208

8.  Synthesis of Chiral Allylic Esters by Using the New Recyclable Chiral Heterogeneous Oxazoline-Based Catalysts.

Authors:  Saadi Samadi; Akram Ashouri; Mojgan Samadi
Journal:  ACS Omega       Date:  2020-08-24

Review 9.  Therapeutic Potential of TAAR1 Agonists in Schizophrenia: Evidence from Preclinical Models and Clinical Studies.

Authors:  Nina Dedic; Heather Dworak; Courtney Zeni; Grazia Rutigliano; Oliver D Howes
Journal:  Int J Mol Sci       Date:  2021-12-07       Impact factor: 5.923
  9 in total

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