Literature DB >> 20005115

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.

Malliga R Iyer1, Yong Sok Lee, Jeffrey R Deschamps, Richard B Rothman, Christina M Dersch, Arthur E Jacobson, Kenner C Rice.   

Abstract

A series of N-substituted rac-cis-4a-ethyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-8-ols have been prepared using a simple synthetic route previously designed for synthesis of related n class="Chemical">cis-2-methyl-4a-alkyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ols. The new phenolic compounds, where the aromatic hydroxy moiety is situated ortho to the oxygen atom in the oxide-bridged ring, do not interact as well as the pyridin-6-ols with opioid receptors. The N-para-fluorophenethyl derivative had the highest mu-opioid receptor affinity of the examined compounds (K(i)=0.35 microM). Published by Elsevier Ltd.

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Year:  2009        PMID： 20005115      PMCID： PMC2818504          DOI： 10.1016/j.bmc.2009.11.022

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  14 in total

1.  Synthesis and in vitro and in vivo activity of (-)-(1R,5R,9R)- and (+)-(1S,5S,9S)-N-alkenyl-, -N-alkynyl-, and -N-cyanoalkyl-5, 9-dimethyl-2'-hydroxy-6,7-benzomorphan homologues.

Authors:  E L May; A E Jacobson; M V Mattson; J R Traynor; J H Woods; L S Harris; E R Bowman; M D Aceto
Journal:  J Med Chem       Date:  2000-12-28       Impact factor: 7.446

2.  Effect of N-alkyl and N-alkenyl substituents in noroxymorphindole, 17-substituted-6,7-dehydro-4,5alpha-epoxy-3,14-dihydroxy-6,7:2',3'-indolomorphinans, on opioid receptor affinity, selectivity, and efficacy.

Authors:  S McLamore; T Ullrich; R B Rothman; H Xu; C Dersch; A Coop; P Davis; F Porreca; A E Jacobson; K C Rice
Journal:  J Med Chem       Date:  2001-04-26       Impact factor: 7.446

3.  Antipodal alpha-N-(methyl through decyl)-N-normetazocines (5,9 alpha-dimethyl-2'-hydroxy-6,7-benzomorphans): in vitro and in vivo properties.

Authors:  E L May; M D Aceto; E R Bowman; C Bentley; B R Martin; L S Harris; F Medzihradsky; M V Mattson; A E Jacobson
Journal:  J Med Chem       Date:  1994-09-30       Impact factor: 7.446

4.  Probes for narcotic receptor mediated phenomena. 9. Synthesis of (+/-)-(3 alpha,6a alpha,11a beta)-1,3,4,5,6,11a-hexahydro-2-methyl-2H-3,6a- methanobenzofuro[2,3-c]azocin-10-ol, an oxide-bridged 5-(m-hydroxyphenyl)morphan.

Authors:  T R Burke; A E Jacobson; K C Rice; B A Weissman; H C Huang; J V Silverton
Journal:  J Med Chem       Date:  1986-05       Impact factor: 7.446

5.  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

6.  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

7.  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.

Authors:  Yi Zhang; Yong Sok Lee; Richard B Rothman; Christina M Dersch; Jeffrey R Deschamps; Arthur E Jacobson; Kenner C Rice
Journal:  J Med Chem       Date:  2009-12-10       Impact factor: 7.446

8.  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

9.  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

10.  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
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  3 in total

1.  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

2.  Probes for narcotic receptor mediated phenomena. 41. Unusual inverse μ-agonists and potent μ-opioid antagonists by modification of the N-substituent in enantiomeric 5-(3-hydroxyphenyl)morphans.

Authors:  Kejun Cheng; Yong Sok Lee; Richard B Rothman; Christina M Dersch; Ross W Bittman; Arthur E Jacobson; Kenner C Rice
Journal:  J Med Chem       Date:  2011-01-19       Impact factor: 7.446

3.  Probes for narcotic receptor mediated phenomena. 47. Novel C4a- and N-substituted-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:  Bioorg Med Chem       Date:  2013-04-03       Impact factor: 3.641
  3 in total

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