Literature DB >> 19627147

Probes for narcotic receptor mediated phenomena. 39. Enantiomeric N-substituted benzofuro[2,3-c]pyridin-6-ols: synthesis and topological relationship to oxide-bridged phenylmorphans.

Yi Zhang1, Yong Sok Lee, Richard B Rothman, Christina M Dersch, Jeffrey R Deschamps, Arthur E Jacobson, Kenner C Rice.   

Abstract

Enantiomers of N-substituted benzofuro[2,3-c]pyridin-6-ols have been synthesized, and the subnanomolar affinity and potent agonist activity of the known racemic N-phenethyl substituted benzofuro[2,3-c]pyridin-6-ol can now be ascribed to the 4aS,9aR enantiomer. The energy-minimized structures suggest that the active enantiomer bears a greater three-dimensional resemblance to morphine than to an ostensibly structurally similar oxide-bridged phenylmorphan. Structural features of the conformers of N-substituted benzofuro[2,3-c]pyridin-6-ols were compared to provide the rationale for their binding affinity.

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Year:  2009        PMID： 19627147      PMCID： PMC2788676          DOI： 10.1021/jm9004225

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


  13 in total

1.  Psychotomimetic phenylisopropylamines. 5. 4-Alkyl-2,5-dimethoxyphenylisopropylamines.

Authors:  A T Shulgin; D C Dyer
Journal:  J Med Chem       Date:  1975-12       Impact factor: 7.446

2.  N-inversion-associated conformational dynamics is unusually rapid in morphine alkaloids.

Authors:  Anatoly M Belostotskii; Zafrir Goren; Hugo E Gottlieb
Journal:  J Nat Prod       Date:  2004-11       Impact factor: 4.050

3.  Opioid peptide receptor studies. 14. Stereochemistry determines agonist efficacy and intrinsic efficacy in the [(35)S]GTP-gamma-S functional binding assay.

Authors:  H Xu; A Hashimoto; K C Rice; A E Jacobson; J B Thomas; F I Carroll; J Lai; R B Rothman
Journal:  Synapse       Date:  2001-01       Impact factor: 2.562

4.  Benzofuro[2,3-c]pyridin-6-ols: synthesis, affinity for opioid-receptor subtypes, and antinociceptive activity.

Authors:  A J Hutchison; R de Jesus; M Williams; J P Simke; R F Neale; R H Jackson; F Ambrose; B J Barbaz; M A Sills
Journal:  J Med Chem       Date:  1989-09       Impact factor: 7.446

5.  Probes for narcotic receptor mediated phenomena. 37. Synthesis and opioid binding affinity of the final pair of oxide-bridged phenylmorphans, the ortho- and para-b-isomers and their N-phenethyl analogues, and the synthesis of the N-phenethyl analogues of the ortho- and para-d-isomers.

Authors:  Muneaki Kurimura; Hehua Liu; Agnieszka Sulima; Akihiro Hashimoto; Anna K Przybyl; Etsuo Ohshima; Shinichi Kodato; Jeffrey R Deschamps; Christina M Dersch; Richard B Rothman; Yong Sok Lee; Arthur E Jacobson; Kenner C Rice
Journal:  J Med Chem       Date:  2008-12-25       Impact factor: 7.446

6.  Synthesis and pharmacological effects of the enantiomers of the N-phenethyl analogues of the ortho and para e- and f-oxide-bridged phenylmorphans.

Authors:  Josef Zezula; Lisa Singer; Anna K Przybył; Akihiro Hashimoto; Christina M Dersch; Richard B Rothman; Jeffrey Deschamps; Yong Sok Lee; Arthur E Jacobson; Kenner C Rice
Journal:  Org Biomol Chem       Date:  2008-06-13       Impact factor: 3.876

7.  Probes for narcotic receptor-mediated phenomena. 33. Construction of a strained trans-5,6-ring system by displacement of a nitro-activated aromatic fluorine. synthesis of the penultimate oxide-bridged phenylmorphans.

Authors:  Akihiro Hashimoto; Anna K Przybyl; Joannes T M Linders; Shinichi Kodato; Xinrong Tian; Jeffrey R Deschamps; Clifford George; Judith L Flippen-Anderson; Arthur E Jacobson; Kenner C Rice
Journal:  J Org Chem       Date:  2004-08-06       Impact factor: 4.354

8.  Synthesis of rac-(1R,4aR,9aR)-2-methyl-1,3,4,9a-tetrahydro-2H-1,4a-propanobenzofuro[2,3-c]pyridin-6-ol. An unusual double rearrangement leading to the ortho- and para-f oxide-bridged phenylmorphan isomers.

Authors:  Shinichi Kodato; Joannes T M Linders; Xiao-Hui Gu; Koichiro Yamada; Judith L Flippen-Anderson; Jeffrey R Deschamps; Arthur E Jacobson; Kenner C Rice
Journal:  Org Biomol Chem       Date:  2004-01-05       Impact factor: 3.876

9.  Probes for narcotic receptor mediated phenomena. 34. Synthesis and structure-activity relationships of a potent mu-agonist delta-antagonist and an exceedingly potent antinociceptive in the enantiomeric C9-substituted 5-(3-hydroxyphenyl)-N-phenylethylmorphan series.

Authors:  Anne-Cécile Hiebel; Yong Sok Lee; Edward Bilsky; Denise Giuvelis; Jeffrey R Deschamps; Damon A Parrish; Mario D Aceto; Everette L May; Louis S Harris; Andrew Coop; Christina M Dersch; John S Partilla; Richard B Rothman; Kejun Cheng; Arthur E Jacobson; Kenner C Rice
Journal:  J Med Chem       Date:  2007-07-11       Impact factor: 7.446

10.  A novel and facile preparation of bremazocine enantiomers through optically pure N-norbremazocines.

Authors:  Elisabeth Greiner; John E Folk; Arthur E Jacobson; Kenner C Rice
Journal:  Bioorg Med Chem       Date:  2004-01-02       Impact factor: 3.641
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  4 in total

1.  Modulation of opioid receptor affinity and efficacy via N-substitution of 9β-hydroxy-5-(3-hydroxyphenyl)morphan: Synthesis and computer simulation study.

Authors:  Phong M Truong; Sergio A Hassan; Yong-Sok Lee; Theresa A Kopajtic; Jonathan L Katz; Aaron M Chadderdon; John R Traynor; Jeffrey R Deschamps; Arthur E Jacobson; Kenner C Rice
Journal:  Bioorg Med Chem       Date:  2017-03-01       Impact factor: 3.641

2.  Probes for narcotic receptor mediated phenomena. 43. Synthesis of the ortho-a and para-a, and improved synthesis and optical resolution of the ortho-b and para-b oxide-bridged phenylmorphans: compounds with moderate to low opioid-receptor affinity.

Authors:  Feng Li; John E Folk; Kejun Cheng; Muneaki Kurimura; Jason A Deck; Jeffrey R Deschamps; Richard B Rothman; Christina M Dersch; Arthur E Jacobson; Kenner C Rice
Journal:  Bioorg Med Chem       Date:  2011-05-24       Impact factor: 3.641

3.  Probes for narcotic receptor mediated phenomena 49. N-substituted rac-cis-4a-arylalkyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ols.

Authors:  Malliga R Iyer; Richard B Rothman; Christina M Dersch; Arthur E Jacobson; Kenner C Rice
Journal:  Eur J Med Chem       Date:  2015-01-13       Impact factor: 6.514

4.  Probes for narcotic receptor mediated phenomena. 40. N-substituted cis-4a-ethyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-8-ols.

Authors:  Malliga R Iyer; Yong Sok Lee; Jeffrey R Deschamps; Richard B Rothman; Christina M Dersch; Arthur E Jacobson; Kenner C Rice
Journal:  Bioorg Med Chem       Date:  2009-11-18       Impact factor: 3.641
  4 in total

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