Literature DB >> 19963374

Triazole oxytocin antagonists: Identification of an aryloxyazetidine replacement for a biaryl substituent.

Alan Brown1, T Bruce Brown, Andrew Calabrese, Dave Ellis, Nicholas Puhalo, Michael Ralph, Lesa Watson.   

Abstract

A series of aryloxyazetidines, aryloxypyrrolidines and aryloxypiperidines were designed based on structural overlap with previously reported arylpyrazine Oxytocin antagonists. Similarly high levels of Oxytocin antagonism were achievable in these new series. Several aryloxyazetidines also showed high levels of selectivity, with one compound, 25, displaying promising in vivo pharmacokinetics and significantly improved aqueous solubility over related compounds containing a biaryl substituent. Copyright 2009 Elsevier Ltd. All rights reserved.

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Year:  2009        PMID: 19963374     DOI: 10.1016/j.bmcl.2009.11.097

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  12 in total

1.  Discovery of SHR1653, a Highly Potent and Selective OTR Antagonist with Improved Blood-Brain Barrier Penetration.

Authors:  Xin Li; Zhigao Zhang; Yang Chen; Hong Wan; Jiakang Sun; Bin Wang; Bingqiang Feng; Bing Hu; Xingxing Shi; Jun Feng; Lei Zhang; Feng He; Chang Bai; Lianshan Zhang; Weikang Tao
Journal:  ACS Med Chem Lett       Date:  2019-05-29       Impact factor: 4.345

Review 2.  Dark Classics in Chemical Neuroscience: 3,4-Methylenedioxymethamphetamine.

Authors:  Lee E Dunlap; Anne M Andrews; David E Olson
Journal:  ACS Chem Neurosci       Date:  2018-07-12       Impact factor: 4.418

3.  Synthesis of azetidines via visible-light-mediated intermolecular [2+2] photocycloadditions.

Authors:  Marc R Becker; Emily R Wearing; Corinna S Schindler
Journal:  Nat Chem       Date:  2020-09-23       Impact factor: 24.427

4.  The Current Status of Drug Discovery for the Oxytocin Receptor.

Authors:  Philippe E Nashar; Aidan A Whitfield; Jiri Mikusek; Tristan A Reekie
Journal:  Methods Mol Biol       Date:  2022

Review 5.  Synthesis of azetidines by aza Paternò-Büchi reactions.

Authors:  Alistair D Richardson; Marc R Becker; Corinna S Schindler
Journal:  Chem Sci       Date:  2020-06-12       Impact factor: 9.825

6.  WAY 267,464, a non-peptide oxytocin receptor agonist, impairs social recognition memory in rats through a vasopressin 1A receptor antagonist action.

Authors:  Callum Hicks; Linnet Ramos; Tristan A Reekie; Rajeshwar Narlawar; Michael Kassiou; Iain S McGregor
Journal:  Psychopharmacology (Berl)       Date:  2015-03-13       Impact factor: 4.530

7.  Acute prosocial effects of oxytocin and vasopressin when given alone or in combination with 3,4-methylenedioxymethamphetamine in rats: involvement of the V1A receptor.

Authors:  Linnet Ramos; Callum Hicks; Richard Kevin; Alex Caminer; Rajeshwar Narlawar; Michael Kassiou; Iain S McGregor
Journal:  Neuropsychopharmacology       Date:  2013-05-16       Impact factor: 7.853

8.  Body temperature and cardiac changes induced by peripherally administered oxytocin, vasopressin and the non-peptide oxytocin receptor agonist WAY 267,464: a biotelemetry study in rats.

Authors:  C Hicks; L Ramos; T Reekie; G H Misagh; R Narlawar; M Kassiou; I S McGregor
Journal:  Br J Pharmacol       Date:  2014-06       Impact factor: 8.739

Review 9.  Put a ring on it: application of small aliphatic rings in medicinal chemistry.

Authors:  Matthias R Bauer; Paolo Di Fruscia; Simon C C Lucas; Iacovos N Michaelides; Jennifer E Nelson; R Ian Storer; Benjamin C Whitehurst
Journal:  RSC Med Chem       Date:  2021-01-07

10.  7-Substituted 2-Nitro-5,6-dihydroimidazo[2,1-b][1,3]oxazines: Novel Antitubercular Agents Lead to a New Preclinical Candidate for Visceral Leishmaniasis.

Authors:  Andrew M Thompson; Patrick D O'Connor; Andrew J Marshall; Vanessa Yardley; Louis Maes; Suman Gupta; Delphine Launay; Stephanie Braillard; Eric Chatelain; Scott G Franzblau; Baojie Wan; Yuehong Wang; Zhenkun Ma; Christopher B Cooper; William A Denny
Journal:  J Med Chem       Date:  2017-05-11       Impact factor: 7.446

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