Cinnamoyl Derivatives of 7α-Aminomethyl-6,14-endoethanotetrahydrothebaine and 7α-Aminomethyl-6,14-endoethanotetrahydrooripavine and Related Opioid Ligands

D Rennison; Adrian P Neal; Gerta Cami-Kobeci; Mario D Aceto; F Martinez-Bermejo; John W Lewis; S M Husbands

doi:10.1021/jm070255o

Cinnamoyl Derivatives of 7α-Aminomethyl-6,14-endoethanotetrahydrothebaine and 7α-Aminomethyl-6,14-endoethanotetrahydrooripavine and Related Opioid Ligands

D Rennison, Adrian P Neal, Gerta Cami-Kobeci, Mario D Aceto, F Martinez-Bermejo, John W Lewis, S M Husbands

Department of Life Sciences

Research output: Contribution to journal › Article › peer-review

15 Citations (SciVal)

Abstract

A new series of ligands has been synthesized where the cinnamoyl group of the 14-cinnamoylamino morphinones has been introduced to the 7α-substituent of the 6,14-bridged oripavine series. In vitro the compounds were mostly low efficacy partial agonists or antagonists with some selectivity for the mu opioid receptor, with evidence of mu efficacy in vivo. The similarity in SAR between these 6,14-bridged oripavines and the 14-cinnamoylamino series suggests a similar mode of interaction with the mu opioid receptor.

Original language	English
Pages (from-to)	5176-5182
Number of pages	7
Journal	Journal of Medicinal Chemistry
Volume	50
Issue number	21
DOIs	https://doi.org/10.1021/jm070255o
Publication status	Published - 2007

Bibliographical note

PMCID: PMC2597403; NIHMSID: NIHMS62675
ID number: PMC2597403

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title = "Cinnamoyl Derivatives of 7α-Aminomethyl-6,14-endoethanotetrahydrothebaine and 7α-Aminomethyl-6,14-endoethanotetrahydrooripavine and Related Opioid Ligands",

abstract = "A new series of ligands has been synthesized where the cinnamoyl group of the 14-cinnamoylamino morphinones has been introduced to the 7α-substituent of the 6,14-bridged oripavine series. In vitro the compounds were mostly low efficacy partial agonists or antagonists with some selectivity for the mu opioid receptor, with evidence of mu efficacy in vivo. The similarity in SAR between these 6,14-bridged oripavines and the 14-cinnamoylamino series suggests a similar mode of interaction with the mu opioid receptor.",

author = "D Rennison and Neal, {Adrian P} and Gerta Cami-Kobeci and Aceto, {Mario D} and F Martinez-Bermejo and Lewis, {John W} and Husbands, {S M}",

note = "PMCID: PMC2597403; NIHMSID: NIHMS62675 ID number: PMC2597403",

year = "2007",

doi = "10.1021/jm070255o",

language = "English",

volume = "50",

pages = "5176--5182",

journal = "Journal of Medicinal Chemistry",

publisher = "American Chemical Society",

number = "21",

}

TY - JOUR

T1 - Cinnamoyl Derivatives of 7α-Aminomethyl-6,14-endoethanotetrahydrothebaine and 7α-Aminomethyl-6,14-endoethanotetrahydrooripavine and Related Opioid Ligands

AU - Rennison, D

AU - Neal, Adrian P

AU - Cami-Kobeci, Gerta

AU - Aceto, Mario D

AU - Martinez-Bermejo, F

AU - Lewis, John W

AU - Husbands, S M

N1 - PMCID: PMC2597403; NIHMSID: NIHMS62675 ID number: PMC2597403

PY - 2007

Y1 - 2007

N2 - A new series of ligands has been synthesized where the cinnamoyl group of the 14-cinnamoylamino morphinones has been introduced to the 7α-substituent of the 6,14-bridged oripavine series. In vitro the compounds were mostly low efficacy partial agonists or antagonists with some selectivity for the mu opioid receptor, with evidence of mu efficacy in vivo. The similarity in SAR between these 6,14-bridged oripavines and the 14-cinnamoylamino series suggests a similar mode of interaction with the mu opioid receptor.

AB - A new series of ligands has been synthesized where the cinnamoyl group of the 14-cinnamoylamino morphinones has been introduced to the 7α-substituent of the 6,14-bridged oripavine series. In vitro the compounds were mostly low efficacy partial agonists or antagonists with some selectivity for the mu opioid receptor, with evidence of mu efficacy in vivo. The similarity in SAR between these 6,14-bridged oripavines and the 14-cinnamoylamino series suggests a similar mode of interaction with the mu opioid receptor.

UR - http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2597403/

UR - http://pubs.acs.org/doi/abs/10.1021/jm070255o

U2 - 10.1021/jm070255o

DO - 10.1021/jm070255o

M3 - Article

VL - 50

SP - 5176

EP - 5182

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

IS - 21

ER -

Cinnamoyl Derivatives of 7α-Aminomethyl-6,14-endoethanotetrahydrothebaine and 7α-Aminomethyl-6,14-endoethanotetrahydrooripavine and Related Opioid Ligands

Abstract

Bibliographical note

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