Literature DB >> 21570305

Probes for narcotic receptor mediated phenomena. Part 42: synthesis and in vitro pharmacological characterization of the N-methyl and N-phenethyl analogues of the racemic ortho-c and para-c oxide-bridged phenylmorphans.

Jin-Hee Kim1, Jeffrey R Deschamps, Richard B Rothman, Christina M Dersch, John E Folk, Kejun Cheng, Arthur E Jacobson, Kenner C Rice.   

Abstract

A new synthesis of N-methyl and n class="Chemical">N-phenethyl substituted ortho-c and para-c oxide-bridged phenylmorphans, using N-benzyl- rather than N-methyl-substituted intermediates, was used and the pharmacological properties of these compounds were determined. The N-phenethyl substituted ortho-c oxide-bridged phenylmorphan(rac-(3R,6aS,11aS)-2-phenethyl-2,3,4,5,6,11a-hexahydro-1H-3,6a-methanobenzofuro[2,3-c]azocin-10-ol (12)) was found to have the highest μ-opioid receptor affinity (K(i)=1.1 nM) of all of the a- through f-oxide-bridged phenylmorphans. Functional data ([³⁵S]GTP-γ-S) showed that the racemate 12 was more than three times more potent than naloxone as an μ-opioid antagonist. Published by Elsevier Ltd.

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Year:  2011        PMID： 21570305      PMCID： PMC3115714          DOI： 10.1016/j.bmc.2011.04.028

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


  9 in total

1.  Synthetic studies of neoclerodane diterpenoids from Salvia splendens and evaluation of Opioid Receptor affinity.

Authors:  Gianfranco Fontana; Giuseppe Savona; Benjamín Rodríguez; Christina M Dersch; Richard B Rothman; Thomas E Prisinzano
Journal:  Tetrahedron       Date:  2008-12-20       Impact factor: 2.457

2.  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

Review 3.  The importance of discerning shape in molecular pharmacology.

Authors:  Sandhya Kortagere; Matthew D Krasowski; Sean Ekins
Journal:  Trends Pharmacol Sci       Date:  2009-01-31       Impact factor: 14.819

4.  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

5.  Molecular shape and medicinal chemistry: a perspective.

Authors:  Anthony Nicholls; Georgia B McGaughey; Robert P Sheridan; Andrew C Good; Gregory Warren; Magali Mathieu; Steven W Muchmore; Scott P Brown; J Andrew Grant; James A Haigh; Neysa Nevins; Ajay N Jain; Brian Kelley
Journal:  J Med Chem       Date:  2010-05-27       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
  9 in total
  3 in total

1.  Probes for narcotic receptor mediated phenomena. 46. N-substituted-2,3,4,9,10,10a-hexahydro-1H-1,4a-(epiminoethano)phenanthren-6- and 8-ols - carbocyclic relatives of f-oxide-bridged phenylmorphans.

Authors:  Fuying Li; Jason A Deck; Christina M Dersch; Richard B Rothman; Jeffrey R Deschamps; Arthur E Jacobson; Kenner C Rice
Journal:  Eur J Med Chem       Date:  2012-10-30       Impact factor: 6.514

2.  Probes for narcotic receptor mediated phenomena. 48. C7- and C8-substituted 5-phenylmorphan opioids from diastereoselective alkylation.

Authors:  Hwan Jung Lim; Christina M Dersch; Richard B Rothman; Jeffrey R Deschamps; Arthur E Jacobson; Kenner C Rice
Journal:  Eur J Med Chem       Date:  2013-06-25       Impact factor: 6.514

3.  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 in total

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