Literature DB >> 34676040

Intramolecular Ring-Opening Decomposition of Aryl Azetidines.

Guoyun Bai1, Thomas N O'Connell1, Michael A Brodney2, Christopher R Butler2, Lara C Czabaniuk1, Adam M Gilbert1, Erik A LaChapelle3, Chao Li1, Laura A McAllister2, Kevin Ogilvie3, Laurence Philippe1, Romelia Salomon-Ferrer4, Michael J Shapiro1, Jeremy T Starr1, Daniel P Uccello1, Jane M Withka1, Jiangli Yan1, Matthew F Brown1.   

Abstract

The ring strain present in azetidines can lead to undesired stability issues. Herein, we described a series of N-substituted azetidines which undergo an acid-mediated intramolecular ring-opening decomposition via nucleophilic attack of a pendant amide group. Studies were conducted to understand the decomposition mechanism enabling the design of stable analogues.
© 2021 American Chemical Society.

Entities:  

Year:  2021        PMID： 34676040      PMCID： PMC8521649          DOI： 10.1021/acsmedchemlett.1c00402

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.632


  7 in total

1.  Metabolism and Bioactivation: It's Time to Expect the Unexpected.

Authors:  James P Driscoll; Corinne M Sadlowski; Nina R Shah; Antonio Feula
Journal:  J Med Chem       Date:  2020-04-21       Impact factor: 7.446

2.  Novel 6,7,8,9-tetrahydro-5H-1,4,7,10a-tetraaza-cyclohepta[f]indene analogues as potent and selective 5-HT(2C) agonists for the treatment of metabolic disorders.

Authors:  Heather Tye; Stephan G Mueller; Juergen Prestle; Stefan Scheuerer; Marcus Schindler; Bernd Nosse; Natacha Prevost; Christopher J Brown; Alexander Heifetz; Clemens Moeller; Anna Pedret-Dunn; Mark Whittaker
Journal:  Bioorg Med Chem Lett       Date:  2010-11-24       Impact factor: 2.823

3.  Hip To Be Square: Oxetanes as Design Elements To Alter Metabolic Pathways.

Authors:  Francesca Toselli; Marlene Fredenwall; Peder Svensson; Xue-Qing Li; Anders Johansson; Lars Weidolf; Martin A Hayes
Journal:  J Med Chem       Date:  2019-08-02       Impact factor: 7.446

4.  Application of Structure-Based Design and Parallel Chemistry to Identify a Potent, Selective, and Brain Penetrant Phosphodiesterase 2A Inhibitor.

Authors:  Christopher J Helal; Eric P Arnold; Tracey L Boyden; Cheng Chang; Thomas A Chappie; Kimberly F Fennell; Michael D Forman; Mihaly Hajos; John F Harms; William E Hoffman; John M Humphrey; Zhijun Kang; Robin J Kleiman; Bethany L Kormos; Che-Wah Lee; Jiemin Lu; Noha Maklad; Laura McDowell; Scot Mente; Rebecca E O'Connor; Jayvardhan Pandit; Mary Piotrowski; Anne W Schmidt; Christopher J Schmidt; Hirokazu Ueno; Patrick R Verhoest; Edward X Yang
Journal:  J Med Chem       Date:  2017-06-16       Impact factor: 7.446

5.  Discovery of highly potent and selective α4β2-nicotinic acetylcholine receptor (nAChR) partial agonists containing an isoxazolylpyridine ether scaffold that demonstrate antidepressant-like activity. Part II.

Authors:  Li-Fang Yu; J Brek Eaton; Allison Fedolak; Han-Kun Zhang; Taleen Hanania; Dani Brunner; Ronald J Lukas; Alan P Kozikowski
Journal:  J Med Chem       Date:  2012-11-02       Impact factor: 7.446

6.  Strategies toward optimization of the metabolism of a series of serotonin-4 partial agonists: investigation of azetidines as piperidine isosteres.

Authors:  Ronald Scott Obach; Erik A LaChapelle; Michael A Brodney; Michelle Vanase-Frawley; Gregory W Kauffman; Aarti Sawant-Basak
Journal:  Xenobiotica       Date:  2016-03-07       Impact factor: 1.908

7.  Metabolism of Strained Rings: Glutathione S-transferase-Catalyzed Formation of a Glutathione-Conjugated Spiro-azetidine without Prior Bioactivation.

Authors:  Xue-Qing Li; Gunnar Grönberg; Eva-Henriette Bangur; Martin A Hayes; Neal Castagnoli; Lars Weidolf
Journal:  Drug Metab Dispos       Date:  2019-09-06       Impact factor: 3.922
  7 in total

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