Synthesis and binding studies of 2-arylapomorphines

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Standard

Synthesis and binding studies of 2-arylapomorphines. / Søndergaard, Kåre; Kristensen, Jesper Langgaard; Palner, Mikael; Gillings, Nic; Knudsen, Gitte Moos; Roth, Bryan; Begtrup, M.

In: Organic & Biomolecular Chemistry, Vol. 3, No. 22, 21.11.2005, p. 4077-4081.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Søndergaard, K, Kristensen, JL, Palner, M, Gillings, N, Knudsen, GM, Roth, B & Begtrup, M 2005, 'Synthesis and binding studies of 2-arylapomorphines', Organic & Biomolecular Chemistry, vol. 3, no. 22, pp. 4077-4081. https://doi.org/10.1039/b507195j

APA

Søndergaard, K., Kristensen, J. L., Palner, M., Gillings, N., Knudsen, G. M., Roth, B., & Begtrup, M. (2005). Synthesis and binding studies of 2-arylapomorphines. Organic & Biomolecular Chemistry, 3(22), 4077-4081. https://doi.org/10.1039/b507195j

Vancouver

Søndergaard K, Kristensen JL, Palner M, Gillings N, Knudsen GM, Roth B et al. Synthesis and binding studies of 2-arylapomorphines. Organic & Biomolecular Chemistry. 2005 Nov 21;3(22):4077-4081. https://doi.org/10.1039/b507195j

Author

Søndergaard, Kåre ; Kristensen, Jesper Langgaard ; Palner, Mikael ; Gillings, Nic ; Knudsen, Gitte Moos ; Roth, Bryan ; Begtrup, M. / Synthesis and binding studies of 2-arylapomorphines. In: Organic & Biomolecular Chemistry. 2005 ; Vol. 3, No. 22. pp. 4077-4081.

Bibtex

@article{4fcbefcdfa3b42fc8aab7f8934c52ef6,
title = "Synthesis and binding studies of 2-arylapomorphines",
abstract = "From codeine, four different 2-aryl substituted apomorphines were synthesised in 6 steps each. Oxidation of codeine with IBX followed by acid catalysed rearrangement gave morphothebaine, which was selectively triflylated at the 2-position and subsequently O-acetylated at the 11-position. The resulting triflate was coupled in a Suzuki-Miyaura type reaction with a series of 4-substituted arylboronic esters which, after deprotection, gave the desired 2-aryl apomorphines. The analogues were tested for affinity towards a range of dopaminergic, serotonergic and adrenergic receptors. 2-(4-Hydroxyphenyl)- apomorphine exhibited high affinity for the dopamine D receptor. A putative ligand-receptor interaction was put forward.",
author = "K{\aa}re S{\o}ndergaard and Kristensen, {Jesper Langgaard} and Mikael Palner and Nic Gillings and Knudsen, {Gitte Moos} and Bryan Roth and M. Begtrup",
year = "2005",
month = nov,
day = "21",
doi = "10.1039/b507195j",
language = "English",
volume = "3",
pages = "4077--4081",
journal = "Organic & Biomolecular Chemistry",
issn = "1470-4358",
publisher = "Royal Society of Chemistry",
number = "22",

}

RIS

TY - JOUR

T1 - Synthesis and binding studies of 2-arylapomorphines

AU - Søndergaard, Kåre

AU - Kristensen, Jesper Langgaard

AU - Palner, Mikael

AU - Gillings, Nic

AU - Knudsen, Gitte Moos

AU - Roth, Bryan

AU - Begtrup, M.

PY - 2005/11/21

Y1 - 2005/11/21

N2 - From codeine, four different 2-aryl substituted apomorphines were synthesised in 6 steps each. Oxidation of codeine with IBX followed by acid catalysed rearrangement gave morphothebaine, which was selectively triflylated at the 2-position and subsequently O-acetylated at the 11-position. The resulting triflate was coupled in a Suzuki-Miyaura type reaction with a series of 4-substituted arylboronic esters which, after deprotection, gave the desired 2-aryl apomorphines. The analogues were tested for affinity towards a range of dopaminergic, serotonergic and adrenergic receptors. 2-(4-Hydroxyphenyl)- apomorphine exhibited high affinity for the dopamine D receptor. A putative ligand-receptor interaction was put forward.

AB - From codeine, four different 2-aryl substituted apomorphines were synthesised in 6 steps each. Oxidation of codeine with IBX followed by acid catalysed rearrangement gave morphothebaine, which was selectively triflylated at the 2-position and subsequently O-acetylated at the 11-position. The resulting triflate was coupled in a Suzuki-Miyaura type reaction with a series of 4-substituted arylboronic esters which, after deprotection, gave the desired 2-aryl apomorphines. The analogues were tested for affinity towards a range of dopaminergic, serotonergic and adrenergic receptors. 2-(4-Hydroxyphenyl)- apomorphine exhibited high affinity for the dopamine D receptor. A putative ligand-receptor interaction was put forward.

UR - http://www.scopus.com/inward/record.url?scp=28444444584&partnerID=8YFLogxK

U2 - 10.1039/b507195j

DO - 10.1039/b507195j

M3 - Journal article

AN - SCOPUS:28444444584

VL - 3

SP - 4077

EP - 4081

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

SN - 1470-4358

IS - 22

ER -

ID: 45437659