Synthesis of [O-methyl-11C]1-(2-chlorophenyl)-5-(4- methoxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide: A potential PET ligand for CB1 receptors

J. S.Dileep Kumar; Jaya Prabhakaran; Victoria Arango; Ramin V. Parsey; Mark D. Underwood; Norman R. Simpson; Suham A. Kassir; Vattoly J. Majo; Ronald L. Van Heertum; J. John Mann

doi:10.1016/j.bmcl.2004.03.034

Synthesis of [O-methyl-¹¹C]1-(2-chlorophenyl)-5-(4- methoxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide: A potential PET ligand for CB₁ receptors

J. S.Dileep Kumar
, Jaya Prabhakaran
, Victoria Arango
, Ramin V. Parsey
, Mark D. Underwood
, Norman R. Simpson
, Suham A. Kassir
, Vattoly J. Majo
, Ronald L. Van Heertum
, J. John Mann

Psychiatry

Stony Brook University

Columbia University

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

17 Scopus citations

Abstract

Synthesis and in vitro evaluation of [O-methyl-¹¹C]1-(2- chlorophenyl)-5-(4-methoxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide ([¹¹C]-1), a potential imaging agent for CB ₁ receptors using PET is described. 1-(2-Chlorophenyl)-5-(4- hydroxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide (5), the precursor for radiolabeling, was synthesized from 4-OTBDPS-propiophenone (2) in five steps with 30% overall yield. The reaction of alcohol 5 with [ ¹¹C]MeOTf at 60°C afforded [¹¹C]-1 with an average radiochemical yield of 14.5% (EOS) and >2000Ci/mmol specific activity. The radiotracer was found to selectively label CB₁ receptors in slide-mounted sections of postmortem human brain containing prefrontal cortex as demonstrated by in vitro autoradiography using phosphor imaging.

Original language	English
Pages (from-to)	2393-2396
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	14
Issue number	10
DOIs	https://doi.org/10.1016/j.bmcl.2004.03.034
State	Published - May 17 2004

Keywords

Autoradiography
Biological imaging
CB receptors
Human postmortem
Positron emission tomography

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10.1016/j.bmcl.2004.03.034

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Kumar, J. S. D., Prabhakaran, J., Arango, V., Parsey, R. V., Underwood, M. D., Simpson, N. R., Kassir, S. A., Majo, V. J., Van Heertum, R. L., & Mann, J. J. (2004). Synthesis of [O-methyl-¹¹C]1-(2-chlorophenyl)-5-(4- methoxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide: A potential PET ligand for CB₁ receptors. Bioorganic and Medicinal Chemistry Letters, 14(10), 2393-2396. https://doi.org/10.1016/j.bmcl.2004.03.034

@article{b1b55a66e4ea47c8811b8c9d8855d082,

title = "Synthesis of [O-methyl-11C]1-(2-chlorophenyl)-5-(4- methoxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide: A potential PET ligand for CB1 receptors",

abstract = "Synthesis and in vitro evaluation of [O-methyl-11C]1-(2- chlorophenyl)-5-(4-methoxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide ([11C]-1), a potential imaging agent for CB 1 receptors using PET is described. 1-(2-Chlorophenyl)-5-(4- hydroxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide (5), the precursor for radiolabeling, was synthesized from 4-OTBDPS-propiophenone (2) in five steps with 30\% overall yield. The reaction of alcohol 5 with [ 11C]MeOTf at 60°C afforded [11C]-1 with an average radiochemical yield of 14.5\% (EOS) and >2000Ci/mmol specific activity. The radiotracer was found to selectively label CB1 receptors in slide-mounted sections of postmortem human brain containing prefrontal cortex as demonstrated by in vitro autoradiography using phosphor imaging.",

keywords = "Autoradiography, Biological imaging, CB receptors, Human postmortem, Positron emission tomography",

author = "Kumar, \{J. S.Dileep\} and Jaya Prabhakaran and Victoria Arango and Parsey, \{Ramin V.\} and Underwood, \{Mark D.\} and Simpson, \{Norman R.\} and Kassir, \{Suham A.\} and Majo, \{Vattoly J.\} and \{Van Heertum\}, \{Ronald L.\} and Mann, \{J. John\}",

year = "2004",

month = may,

day = "17",

doi = "10.1016/j.bmcl.2004.03.034",

language = "English",

volume = "14",

pages = "2393--2396",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Ltd.",

number = "10",

}

Kumar, JSD, Prabhakaran, J, Arango, V, Parsey, RV, Underwood, MD, Simpson, NR, Kassir, SA, Majo, VJ, Van Heertum, RL & Mann, JJ 2004, 'Synthesis of [O-methyl-¹¹C]1-(2-chlorophenyl)-5-(4- methoxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide: A potential PET ligand for CB₁ receptors', Bioorganic and Medicinal Chemistry Letters, vol. 14, no. 10, pp. 2393-2396. https://doi.org/10.1016/j.bmcl.2004.03.034

Synthesis of [O-methyl-¹¹C]1-(2-chlorophenyl)-5-(4- methoxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide: A potential PET ligand for CB₁ receptors. / Kumar, J. S.Dileep; Prabhakaran, Jaya; Arango, Victoria et al.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 14, No. 10, 17.05.2004, p. 2393-2396.

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

TY - JOUR

T1 - Synthesis of [O-methyl-11C]1-(2-chlorophenyl)-5-(4- methoxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide

T2 - A potential PET ligand for CB1 receptors

AU - Kumar, J. S.Dileep

AU - Prabhakaran, Jaya

AU - Arango, Victoria

AU - Parsey, Ramin V.

AU - Underwood, Mark D.

AU - Simpson, Norman R.

AU - Kassir, Suham A.

AU - Majo, Vattoly J.

AU - Van Heertum, Ronald L.

AU - Mann, J. John

PY - 2004/5/17

Y1 - 2004/5/17

N2 - Synthesis and in vitro evaluation of [O-methyl-11C]1-(2- chlorophenyl)-5-(4-methoxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide ([11C]-1), a potential imaging agent for CB 1 receptors using PET is described. 1-(2-Chlorophenyl)-5-(4- hydroxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide (5), the precursor for radiolabeling, was synthesized from 4-OTBDPS-propiophenone (2) in five steps with 30% overall yield. The reaction of alcohol 5 with [ 11C]MeOTf at 60°C afforded [11C]-1 with an average radiochemical yield of 14.5% (EOS) and >2000Ci/mmol specific activity. The radiotracer was found to selectively label CB1 receptors in slide-mounted sections of postmortem human brain containing prefrontal cortex as demonstrated by in vitro autoradiography using phosphor imaging.

AB - Synthesis and in vitro evaluation of [O-methyl-11C]1-(2- chlorophenyl)-5-(4-methoxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide ([11C]-1), a potential imaging agent for CB 1 receptors using PET is described. 1-(2-Chlorophenyl)-5-(4- hydroxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide (5), the precursor for radiolabeling, was synthesized from 4-OTBDPS-propiophenone (2) in five steps with 30% overall yield. The reaction of alcohol 5 with [ 11C]MeOTf at 60°C afforded [11C]-1 with an average radiochemical yield of 14.5% (EOS) and >2000Ci/mmol specific activity. The radiotracer was found to selectively label CB1 receptors in slide-mounted sections of postmortem human brain containing prefrontal cortex as demonstrated by in vitro autoradiography using phosphor imaging.

KW - Autoradiography

KW - Biological imaging

KW - CB receptors

KW - Human postmortem

KW - Positron emission tomography

UR - https://www.scopus.com/pages/publications/11144353911

U2 - 10.1016/j.bmcl.2004.03.034

DO - 10.1016/j.bmcl.2004.03.034

M3 - Article

C2 - 15109619

SN - 0960-894X

VL - 14

SP - 2393

EP - 2396

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 10

ER -

Synthesis of [O-methyl-¹¹C]1-(2-chlorophenyl)-5-(4- methoxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide: A potential PET ligand for CB₁ receptors

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