Multistep Continuous-Flow Synthesis in Medicinal Chemistry: Discovery and Preliminary Structure-Activity Relationships of CCR8 Ligands

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

Standard

Multistep Continuous-Flow Synthesis in Medicinal Chemistry : Discovery and Preliminary Structure-Activity Relationships of CCR8 Ligands. / Petersen, Trine P; Mirsharghi, Sahar; Rummel, Pia Cwarzko; Thiele, Stefanie; Rosenkilde, Mette M; Ritzén, Andreas; Ulven, Trond.

In: Chemistry: A European Journal, Vol. 19, No. 28, 08.07.2013, p. 9343-50.

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

Harvard

Petersen, TP, Mirsharghi, S, Rummel, PC, Thiele, S, Rosenkilde, MM, Ritzén, A & Ulven, T 2013, 'Multistep Continuous-Flow Synthesis in Medicinal Chemistry: Discovery and Preliminary Structure-Activity Relationships of CCR8 Ligands', Chemistry: A European Journal, vol. 19, no. 28, pp. 9343-50. https://doi.org/10.1002/chem.201204350

APA

Petersen, T. P., Mirsharghi, S., Rummel, P. C., Thiele, S., Rosenkilde, M. M., Ritzén, A., & Ulven, T. (2013). Multistep Continuous-Flow Synthesis in Medicinal Chemistry: Discovery and Preliminary Structure-Activity Relationships of CCR8 Ligands. Chemistry: A European Journal, 19(28), 9343-50. https://doi.org/10.1002/chem.201204350

Vancouver

Petersen TP, Mirsharghi S, Rummel PC, Thiele S, Rosenkilde MM, Ritzén A et al. Multistep Continuous-Flow Synthesis in Medicinal Chemistry: Discovery and Preliminary Structure-Activity Relationships of CCR8 Ligands. Chemistry: A European Journal. 2013 Jul 8;19(28):9343-50. https://doi.org/10.1002/chem.201204350

Author

Petersen, Trine P ; Mirsharghi, Sahar ; Rummel, Pia Cwarzko ; Thiele, Stefanie ; Rosenkilde, Mette M ; Ritzén, Andreas ; Ulven, Trond. / Multistep Continuous-Flow Synthesis in Medicinal Chemistry : Discovery and Preliminary Structure-Activity Relationships of CCR8 Ligands. In: Chemistry: A European Journal. 2013 ; Vol. 19, No. 28. pp. 9343-50.

Bibtex

@article{c939dce179c44062ba0e66ce98c81dd1,
title = "Multistep Continuous-Flow Synthesis in Medicinal Chemistry: Discovery and Preliminary Structure-Activity Relationships of CCR8 Ligands",
abstract = "A three-step continuous-flow synthesis system and its application to the assembly of a new series of chemokine receptor ligands directly from commercial building blocks is reported. No scavenger columns or solvent switches are necessary to recover the desired test compounds, which were obtained in overall yields of 49-94 %. The system is modular and flexible, and the individual steps of the sequence can be interchanged with similar outcome, extending the scope of the chemistry. Biological evaluation confirmed activity on the chemokine CCR8 receptor and provided initial structure-activity-relationship (SAR) information for this new ligand series, with the most potent member displaying full agonist activity with single-digit nanomolar potency. To the best of our knowledge, this represents the first published example of efficient use of multistep flow synthesis combined with biological testing and SAR studies in medicinal chemistry.",
author = "Petersen, {Trine P} and Sahar Mirsharghi and Rummel, {Pia Cwarzko} and Stefanie Thiele and Rosenkilde, {Mette M} and Andreas Ritz{\'e}n and Trond Ulven",
note = "Copyright {\textcopyright} 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",
year = "2013",
month = jul,
day = "8",
doi = "10.1002/chem.201204350",
language = "English",
volume = "19",
pages = "9343--50",
journal = "Chemistry: A European Journal",
issn = "0947-6539",
publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
number = "28",

}

RIS

TY - JOUR

T1 - Multistep Continuous-Flow Synthesis in Medicinal Chemistry

T2 - Discovery and Preliminary Structure-Activity Relationships of CCR8 Ligands

AU - Petersen, Trine P

AU - Mirsharghi, Sahar

AU - Rummel, Pia Cwarzko

AU - Thiele, Stefanie

AU - Rosenkilde, Mette M

AU - Ritzén, Andreas

AU - Ulven, Trond

N1 - Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

PY - 2013/7/8

Y1 - 2013/7/8

N2 - A three-step continuous-flow synthesis system and its application to the assembly of a new series of chemokine receptor ligands directly from commercial building blocks is reported. No scavenger columns or solvent switches are necessary to recover the desired test compounds, which were obtained in overall yields of 49-94 %. The system is modular and flexible, and the individual steps of the sequence can be interchanged with similar outcome, extending the scope of the chemistry. Biological evaluation confirmed activity on the chemokine CCR8 receptor and provided initial structure-activity-relationship (SAR) information for this new ligand series, with the most potent member displaying full agonist activity with single-digit nanomolar potency. To the best of our knowledge, this represents the first published example of efficient use of multistep flow synthesis combined with biological testing and SAR studies in medicinal chemistry.

AB - A three-step continuous-flow synthesis system and its application to the assembly of a new series of chemokine receptor ligands directly from commercial building blocks is reported. No scavenger columns or solvent switches are necessary to recover the desired test compounds, which were obtained in overall yields of 49-94 %. The system is modular and flexible, and the individual steps of the sequence can be interchanged with similar outcome, extending the scope of the chemistry. Biological evaluation confirmed activity on the chemokine CCR8 receptor and provided initial structure-activity-relationship (SAR) information for this new ligand series, with the most potent member displaying full agonist activity with single-digit nanomolar potency. To the best of our knowledge, this represents the first published example of efficient use of multistep flow synthesis combined with biological testing and SAR studies in medicinal chemistry.

U2 - 10.1002/chem.201204350

DO - 10.1002/chem.201204350

M3 - Journal article

C2 - 23716302

VL - 19

SP - 9343

EP - 9350

JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

SN - 0947-6539

IS - 28

ER -

ID: 47965332