Microwave-assisted organic synthesis of a high-affinity pyrazolo-pyrimidinyl TSPO ligand

Dewei Tang; Jason R. Buck; Matthew R. Hight; H. Charles Manning

doi:10.1016/j.tetlet.2010.06.074

Microwave-assisted organic synthesis of a high-affinity pyrazolo-pyrimidinyl TSPO ligand

Dewei Tang, Jason R. Buck, Matthew R. Hight, H. Charles Manning

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

14 Scopus citations

Abstract

We herein report a dramatically improved total synthesis of the high-affinity translocator protein (TSPO) ligand DPA-714, featuring microwave-assisted organic synthesis (MAOS). Compared with previously described approaches, our novel MAOS method dramatically reduces overall reaction time without adversely effecting reaction yields. We envision that the described MAOS protocol may be suitably applied to high-throughput, diversity-oriented synthesis of novel compounds based on the pyrazolo-pyrimidinyl scaffold. Such an approach could accelerate the development of focused libraries of novel TSPO ligands with potential for future development as molecular imaging and therapeutic agents.

Original language	English (US)
Pages (from-to)	4595-4598
Number of pages	4
Journal	Tetrahedron Letters
Volume	51
Issue number	35
DOIs	https://doi.org/10.1016/j.tetlet.2010.06.074
State	Published - Sep 1 2010
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2010.06.074

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title = "Microwave-assisted organic synthesis of a high-affinity pyrazolo-pyrimidinyl TSPO ligand",

abstract = "We herein report a dramatically improved total synthesis of the high-affinity translocator protein (TSPO) ligand DPA-714, featuring microwave-assisted organic synthesis (MAOS). Compared with previously described approaches, our novel MAOS method dramatically reduces overall reaction time without adversely effecting reaction yields. We envision that the described MAOS protocol may be suitably applied to high-throughput, diversity-oriented synthesis of novel compounds based on the pyrazolo-pyrimidinyl scaffold. Such an approach could accelerate the development of focused libraries of novel TSPO ligands with potential for future development as molecular imaging and therapeutic agents.",

author = "Dewei Tang and Buck, {Jason R.} and Hight, {Matthew R.} and Manning, {H. Charles}",

note = "Funding Information: The authors wish to gratefully acknowledge funding from the National Cancer Institute (NCI) : 1R01 CA140628 , K25 CA127349 , and 1P50CA128323 (Vanderbilt ICMIC Program). We thank Dr(s). Ronald Baldwin, Ph.D. and R. Adam Smith, Ph.D. for editorial input and insightful discussion. ",

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doi = "10.1016/j.tetlet.2010.06.074",

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T1 - Microwave-assisted organic synthesis of a high-affinity pyrazolo-pyrimidinyl TSPO ligand

AU - Tang, Dewei

AU - Buck, Jason R.

AU - Hight, Matthew R.

AU - Manning, H. Charles

N1 - Funding Information: The authors wish to gratefully acknowledge funding from the National Cancer Institute (NCI) : 1R01 CA140628 , K25 CA127349 , and 1P50CA128323 (Vanderbilt ICMIC Program). We thank Dr(s). Ronald Baldwin, Ph.D. and R. Adam Smith, Ph.D. for editorial input and insightful discussion.

PY - 2010/9/1

Y1 - 2010/9/1

N2 - We herein report a dramatically improved total synthesis of the high-affinity translocator protein (TSPO) ligand DPA-714, featuring microwave-assisted organic synthesis (MAOS). Compared with previously described approaches, our novel MAOS method dramatically reduces overall reaction time without adversely effecting reaction yields. We envision that the described MAOS protocol may be suitably applied to high-throughput, diversity-oriented synthesis of novel compounds based on the pyrazolo-pyrimidinyl scaffold. Such an approach could accelerate the development of focused libraries of novel TSPO ligands with potential for future development as molecular imaging and therapeutic agents.

AB - We herein report a dramatically improved total synthesis of the high-affinity translocator protein (TSPO) ligand DPA-714, featuring microwave-assisted organic synthesis (MAOS). Compared with previously described approaches, our novel MAOS method dramatically reduces overall reaction time without adversely effecting reaction yields. We envision that the described MAOS protocol may be suitably applied to high-throughput, diversity-oriented synthesis of novel compounds based on the pyrazolo-pyrimidinyl scaffold. Such an approach could accelerate the development of focused libraries of novel TSPO ligands with potential for future development as molecular imaging and therapeutic agents.

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JO - Tetrahedron Letters

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Microwave-assisted organic synthesis of a high-affinity pyrazolo-pyrimidinyl TSPO ligand

Abstract

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