Synthesis and pharmacological evaluation of N-benzyl substituted 4-bromo-2,5-dimethoxyphenethylamines as 5-HT2A/2C partial agonists

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

Standard

Synthesis and pharmacological evaluation of N-benzyl substituted 4-bromo-2,5-dimethoxyphenethylamines as 5-HT2A/2C partial agonists. / Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard.

In: Bioorganic & Medicinal Chemistry, Vol. 23, No. 14, 2015, p. 3933-3937.

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

Harvard

Hansen, M, Jacobsen, SE, Plunkett, S, Liebscher, GE, McCorvy, JD, Bräuner-Osborne, H & Kristensen, JL 2015, 'Synthesis and pharmacological evaluation of N-benzyl substituted 4-bromo-2,5-dimethoxyphenethylamines as 5-HT2A/2C partial agonists', Bioorganic & Medicinal Chemistry, vol. 23, no. 14, pp. 3933-3937. https://doi.org/10.1016/j.bmc.2014.12.011

APA

Hansen, M., Jacobsen, S. E., Plunkett, S., Liebscher, G. E., McCorvy, J. D., Bräuner-Osborne, H., & Kristensen, J. L. (2015). Synthesis and pharmacological evaluation of N-benzyl substituted 4-bromo-2,5-dimethoxyphenethylamines as 5-HT2A/2C partial agonists. Bioorganic & Medicinal Chemistry, 23(14), 3933-3937. https://doi.org/10.1016/j.bmc.2014.12.011

Vancouver

Hansen M, Jacobsen SE, Plunkett S, Liebscher GE, McCorvy JD, Bräuner-Osborne H et al. Synthesis and pharmacological evaluation of N-benzyl substituted 4-bromo-2,5-dimethoxyphenethylamines as 5-HT2A/2C partial agonists. Bioorganic & Medicinal Chemistry. 2015;23(14):3933-3937. https://doi.org/10.1016/j.bmc.2014.12.011

Author

Hansen, Martin ; Jacobsen, Stine Engesgaard ; Plunkett, Shane ; Liebscher, Gudrun Eckhard ; McCorvy, John D ; Bräuner-Osborne, Hans ; Kristensen, Jesper Langgaard. / Synthesis and pharmacological evaluation of N-benzyl substituted 4-bromo-2,5-dimethoxyphenethylamines as 5-HT2A/2C partial agonists. In: Bioorganic & Medicinal Chemistry. 2015 ; Vol. 23, No. 14. pp. 3933-3937.

Bibtex

@article{6d493817d36e4573bc1e9e20dccff0fa,
title = "Synthesis and pharmacological evaluation of N-benzyl substituted 4-bromo-2,5-dimethoxyphenethylamines as 5-HT2A/2C partial agonists",
abstract = "N-Benzyl substitution of phenethylamine 5-HT2A receptor agonists has dramatic effects on binding affinity, receptor selectivity and agonist activity. In this paper we examine how affinity for the 5-HT2A/2C receptors are influenced by N-benzyl substitution of 4-bromo-2,5-dimethoxyphenethylamine derivatives. Special attention is given to the 2' and 3'-position of the N-benzyl as such compounds are known to be very potent. We found that substitutions in these positions are generally well tolerated. The 2'-position was further examined using a range of substituents to probe the hydrogen bonding requirements for optimal affinity and selectivity, and it was found that small changes in the ligands in this area had a profound effect on their affinities. Furthermore, two ligands that lack a 2'-benzyl substituent were also found to have high affinity contradicting previous held notions. Several high-affinity ligands were identified and assayed for functional activity at the 5-HT2A and 5-HT2C receptor, and they were generally found to be less efficacious agonists than previously reported N-benzyl phenethylamines.",
author = "Martin Hansen and Jacobsen, {Stine Engesgaard} and Shane Plunkett and Liebscher, {Gudrun Eckhard} and McCorvy, {John D} and Hans Br{\"a}uner-Osborne and Kristensen, {Jesper Langgaard}",
note = "Copyright {\textcopyright} 2014 Elsevier Ltd. All rights reserved.",
year = "2015",
doi = "10.1016/j.bmc.2014.12.011",
language = "English",
volume = "23",
pages = "3933--3937",
journal = "Bioorganic & Medicinal Chemistry",
issn = "0968-0896",
publisher = "Pergamon Press",
number = "14",

}

RIS

TY - JOUR

T1 - Synthesis and pharmacological evaluation of N-benzyl substituted 4-bromo-2,5-dimethoxyphenethylamines as 5-HT2A/2C partial agonists

AU - Hansen, Martin

AU - Jacobsen, Stine Engesgaard

AU - Plunkett, Shane

AU - Liebscher, Gudrun Eckhard

AU - McCorvy, John D

AU - Bräuner-Osborne, Hans

AU - Kristensen, Jesper Langgaard

N1 - Copyright © 2014 Elsevier Ltd. All rights reserved.

PY - 2015

Y1 - 2015

N2 - N-Benzyl substitution of phenethylamine 5-HT2A receptor agonists has dramatic effects on binding affinity, receptor selectivity and agonist activity. In this paper we examine how affinity for the 5-HT2A/2C receptors are influenced by N-benzyl substitution of 4-bromo-2,5-dimethoxyphenethylamine derivatives. Special attention is given to the 2' and 3'-position of the N-benzyl as such compounds are known to be very potent. We found that substitutions in these positions are generally well tolerated. The 2'-position was further examined using a range of substituents to probe the hydrogen bonding requirements for optimal affinity and selectivity, and it was found that small changes in the ligands in this area had a profound effect on their affinities. Furthermore, two ligands that lack a 2'-benzyl substituent were also found to have high affinity contradicting previous held notions. Several high-affinity ligands were identified and assayed for functional activity at the 5-HT2A and 5-HT2C receptor, and they were generally found to be less efficacious agonists than previously reported N-benzyl phenethylamines.

AB - N-Benzyl substitution of phenethylamine 5-HT2A receptor agonists has dramatic effects on binding affinity, receptor selectivity and agonist activity. In this paper we examine how affinity for the 5-HT2A/2C receptors are influenced by N-benzyl substitution of 4-bromo-2,5-dimethoxyphenethylamine derivatives. Special attention is given to the 2' and 3'-position of the N-benzyl as such compounds are known to be very potent. We found that substitutions in these positions are generally well tolerated. The 2'-position was further examined using a range of substituents to probe the hydrogen bonding requirements for optimal affinity and selectivity, and it was found that small changes in the ligands in this area had a profound effect on their affinities. Furthermore, two ligands that lack a 2'-benzyl substituent were also found to have high affinity contradicting previous held notions. Several high-affinity ligands were identified and assayed for functional activity at the 5-HT2A and 5-HT2C receptor, and they were generally found to be less efficacious agonists than previously reported N-benzyl phenethylamines.

U2 - 10.1016/j.bmc.2014.12.011

DO - 10.1016/j.bmc.2014.12.011

M3 - Journal article

C2 - 25583099

VL - 23

SP - 3933

EP - 3937

JO - Bioorganic & Medicinal Chemistry

JF - Bioorganic & Medicinal Chemistry

SN - 0968-0896

IS - 14

ER -

ID: 130101122