Literature DB >> 20495617

Rapid access to morphinones: removal of 4, 5-ether bridge with Pd-catalyzed triflate reduction.

Christopher D Hupp1, John L Neumeyer.   

Abstract

A new synthetic method for the removal of the 4, 5-bridged ether moiety of several opioids has been developed. This process offers a faster, simpler synthetic route to obtain the morphinone scaffold in high yields without the need for protection of the ketone moiety.

Entities:  

Year:  2010        PMID： 20495617      PMCID： PMC2872489          DOI： 10.1016/j.tetlet.2010.02.146

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  24 in total

1.  delta Opioid affinity and selectivity of 4-hydroxy-3-methoxyindolomorphinan analogues related to naltrindole.

Authors:  A Coop; R B Rothman; C Dersch; J Partilla; F Porreca; P Davis; A E Jacobson; K C Rice
Journal:  J Med Chem       Date:  1999-05-06       Impact factor: 7.446

Review 2.  Recent advances in selective opioid receptor agonists and antagonists.

Authors:  Masakatsu Eguchi
Journal:  Med Res Rev       Date:  2004-03       Impact factor: 12.944

3.  Synthesis and preliminary in vitro investigation of bivalent ligands containing homo- and heterodimeric pharmacophores at mu, delta, and kappa opioid receptors.

Authors:  Xuemei Peng; Brian I Knapp; Jean M Bidlack; John L Neumeyer
Journal:  J Med Chem       Date:  2006-01-12       Impact factor: 7.446

4.  Synthesis and pharmacological evaluation of 6,7-indolo/thiazolo-morphinans--further SAR of levorphanol.

Authors:  Ao Zhang; Fuying Li; Chunyong Ding; Qizhen Yao; Brian I Knapp; Jean M Bidlack; John L Neumeyer
Journal:  J Med Chem       Date:  2007-05-09       Impact factor: 7.446

5.  Synthesis of a new opioid ligand having the oxabicyclo[3.2.1]octane skeleton using a new rearrangement reaction.

Authors:  Akio Watanabe; Hideaki Fujii; Mayumi Nakajima; Ko Hasebe; Hidenori Mochizuki; Hiroshi Nagase
Journal:  Bioorg Med Chem Lett       Date:  2009-03-21       Impact factor: 2.823

6.  Elimination of the 4-hydroxyl group of the alkaloids related to morphine. XI. Synthesis of (minus)-14 hydroxy-3-methoxy-N-methylmorphinan derivatives.

Authors:  Y K Sawa; H Tada
Journal:  Tetrahedron       Date:  1968-10       Impact factor: 2.457

7.  Biomimetic synthesis of (+/-)-galanthamine and asymmetric synthesis of (-)-galanthamine using remote asymmetric induction.

Authors:  Manabu Node; Sumiaki Kodama; Yoshio Hamashima; Takahiro Katoh; Kiyoharu Nishide; Tetsuya Kajimoto
Journal:  Chem Pharm Bull (Tokyo)       Date:  2006-12       Impact factor: 1.645

8.  Catalytic aerobic oxidation of nor-binaltorphimine (nor-BNI) analogs without 4,5-epoxy bridge affords a more selective ligand for kappa opioid receptor than the representative kappa antagonist nor-BNI.

Authors:  Yumiko Osa; Yoshihiro Ida; Hideaki Fujii; Toru Nemoto; Ko Hasebe; Shinobu Momen; Hidenori Mochizuki; Hiroshi Nagase
Journal:  Chem Pharm Bull (Tokyo)       Date:  2007-10       Impact factor: 1.645

9.  Novel synthesis of a 1,3,5-trioxazatriquinane skeleton using a nitrogen clamp.

Authors:  Hiroshi Nagase; Akio Watanabe; Masaya Harada; Mayumi Nakajima; Ko Hasebe; Hidenori Mochizuki; Kenji Yoza; Hideaki Fujii
Journal:  Org Lett       Date:  2009-02-05       Impact factor: 6.005

10.  10-Ketomorphinan and 3-substituted-3-desoxymorphinan analogues as mixed kappa and micro opioid ligands: synthesis and biological evaluation of their binding affinity at opioid receptors.

Authors:  Ao Zhang; Wennan Xiong; Jean M Bidlack; James E Hilbert; Brian I Knapp; Mark P Wentland; John L Neumeyer
Journal:  J Med Chem       Date:  2004-01-01       Impact factor: 7.446
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  5 in total

1.  Synthesis, binding affinity, and functional in vitro activity of 3-benzylaminomorphinan and 3-benzylaminomorphine ligands at opioid receptors.

Authors:  John L Neumeyer; Bin Zhang; Tangzhi Zhang; Anna W Sromek; Brian I Knapp; Dana J Cohen; Jean M Bidlack
Journal:  J Med Chem       Date:  2012-04-04       Impact factor: 7.446

2.  Synthesis and Evaluation of Fluorinated Aporphines: Potential Positron Emission Tomography Ligands for D2 Receptors

Authors:  Anna W Sromek; Yu-Gui Si; Tangzhi Zhang; Susan R George; Philip Seeman; John L Neumeyer
Journal:  ACS Med Chem Lett       Date:  2011-03-10       Impact factor: 4.345

3.  Practical Strategy to 1,1'-Dideoxygossypol Derivatives from Gossypol and Its Antitumor Activities.

Authors:  Wei Wang; Yuzhi Lu; Juncheng Ge; Niya Liu
Journal:  ACS Omega       Date:  2022-06-22

4.  Synthesis and pharmacological evaluation of aminothiazolomorphinans at the mu and kappa opioid receptors.

Authors:  Brian A Provencher; Anna W Sromek; Wei Li; Shayla Russell; Elena Chartoff; Brian I Knapp; Jean M Bidlack; John L Neumeyer
Journal:  J Med Chem       Date:  2013-10-29       Impact factor: 7.446

5.  Controlling opioid receptor functional selectivity by targeting distinct subpockets of the orthosteric site.

Authors:  Rajendra Uprety; Tao Che; Saheem A Zaidi; Steven G Grinnell; Balázs R Varga; Abdelfattah Faouzi; Samuel T Slocum; Abdullah Allaoa; András Varadi; Melissa Nelson; Sarah M Bernhard; Elizaveta Kulko; Valerie Le Rouzic; Shainnel O Eans; Chloe A Simons; Amanda Hunkele; Joan Subrath; Ying Xian Pan; Jonathan A Javitch; Jay P McLaughlin; Bryan L Roth; Gavril W Pasternak; Vsevolod Katritch; Susruta Majumdar
Journal:  Elife       Date:  2021-02-08       Impact factor: 8.140
  5 in total

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