Synthesis of [O-methyl-11C]-4-(1,3-dimethoxy-2-propylamino)-2,7-dimethyl-8-(2,4-dichlorophenyl)[1,5-a]pyrazolo-1,3,5-triazine ([11C]DMP696):: a potential PET ligand for CRF1 receptors

被引:11
|
作者
Kumar, JSD
Majo, VJ
Simpson, NR
Prabhakaran, J
Van Heertum, RL
Mann, JJ
机构
[1] Columbia Univ, Dept Psychiat, New York, NY 10032 USA
[2] Columbia Univ, Div Neurosci, New York, NY 10032 USA
[3] New York State Psychiat Inst & Hosp, New York, NY 10032 USA
[4] Columbia Univ, Dept Radiol, New York, NY 10032 USA
关键词
CRF antagonist; positron emission tomography; radiotracer; DMP696;
D O I
10.1002/jlcr.885
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
Synthesis of [O-methyl-C-11]-4-(1,3-dimethoxy-2-propylamino)-2,7-dimethyl-8-(2,4-dichlorophenyl)[1,5-a]pyrazolo-1,3,5-triazine ([C-11]DMP696), a highly selective CRF1 antagonist has been achieved. The total time required for the synthesis of [C-11]DMP696 is 30 min from EOB, using [C-11]methyl triflate in THF, with a 16% yield (EOS) and >99% chemical and radiochemical purities along with a specific activity of >2000 Ci/mmol (EOS). Copyright (C) 2004 John Wiley Sons, Ltd.
引用
收藏
页码:971 / 976
页数:6
相关论文
共 11 条
  • [1] Synthesis of [N-methyl-11C]-3-[(6-dimethylamino)pyridin-3-yl]-2,5-dimethyl-N,N-dipropylpyrazolo[1,5-a]pyrimidine-7-amine:: A potential PET ligand for in vivo imaging of CRF1 receptors
    Kumar, JSD
    Majo, VJ
    Prabhakaran, J
    Simpson, NR
    Van Heertum, RL
    Mann, JJ
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2003, 46 (11) : 1055 - 1065
  • [2] Synthesis, in vitro and in vivo evaluation of [O-methyl-11C] 2-{4-[4-(3-methoxyphenyl)piperazin-1-yl]-butyl}-4-methyl-2H-[1,2,4]-triazine-3,5-dione:: A novel agonist 5-HT1A receptor PET ligand
    Prabhakaran, J
    Parsey, RV
    Majo, VJ
    Hsiung, SC
    Milak, MS
    Tamir, H
    Simpson, NR
    Van Heertum, RL
    Mann, JJ
    Kumar, JSD
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (08) : 2101 - 2104
  • [3] Synthesis of 1-(2,4-dichlorophenyl)-4-cyano-5-(4[11C]methoxyphenyl)-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide ([11C]JHU75528) and 1-(2bromophenyl)-4-cyano-5-(4-[11C]methoxyphenyl)-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide ([11C]JHU75575) as potential radioligands for PET imaging of cerebral cannabinoid receptor
    Fan, Hong
    Ravert, Hayden T.
    Holt, Daniel P.
    Dannals, Robert F.
    Horti, Andrew G.
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2006, 49 (12) : 1021 - 1036
  • [4] 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, JSD
    Prabhakaran, J
    Arango, V
    Parsey, RV
    Underwood, MD
    Simpson, NR
    Kassir, SA
    Majo, VJ
    Van Heertum, RL
    Mann, JJ
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (10) : 2393 - 2396
  • [5] [O-methyl-11C]N-(4-(4-(3-Chloro-2-methoxyphenyl)-piperazin-1-yl)butyl)-1H-indole-2-carboxamide ([11C]BAK4-51) Is an Efflux Transporter Substrate and Ineffective for PET Imaging of Brain D3 Receptors in Rodents and Monkey
    Liow, Jeih-San
    Morse, Cheryl L.
    Lu, Shuiyu
    Frankland, Michael
    Tye, George L.
    Zoghbi, Sami S.
    Gladding, Robert L.
    Shaik, Anver B.
    Innis, Robert B.
    Newman, Amy H.
    Pike, Victor W.
    MOLECULES, 2018, 23 (11):
  • [6] Synthesis and evaluation of [O-methyl-11C]4-[3-[4-(2-methoxyphenyl)-piperazin-1-yl]propoxyl-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione as a 5-HT1A receptor agonist PET ligand
    Majo, Vattoly J.
    Parsey, Ramin V.
    Prabhakaran, Jaya
    Mann, J. John
    Kumar, J. S. Dileep
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2008, 51 (3-4) : 132 - 136
  • [7] Synthesis and initial PET imaging of new potential NK1 receptor radioligands 1-[2-(3,5-bis-trifluoromethyl-benzyloxy)-1-phenyl-ethyl]-4-[11C]methyl-piperazine and {4-[2-(3,5-bis-trifluoromethyl-benzyloxy)-1-phenyl-ethyl]-piperazine-1-yl}-acetic acid [11C]methyl ester
    Gao, MZ
    Mock, BH
    Hutchins, GD
    Zheng, QH
    NUCLEAR MEDICINE AND BIOLOGY, 2005, 32 (05) : 543 - 552
  • [8] Synthesis and in vivo evaluation of a novel 5-HT1A receptor agonist radioligand [O-methyl-11C]2-(4-(4-(2-methoxyphenyl) piperazin-1-yl)butyl)-4-methyl-1,2,4-triazine-3, 5(2H,4H)dione in nonhuman primates
    Kumar, J. S. Dileep
    Prabhakaran, Jaya
    Majo, Vattoly J.
    Milak, Matthew S.
    Hsiung, Shu-Chi
    Tamir, Hadassah
    Simpson, Norman R.
    Van Heertum, Ronald L.
    Mann, J. John
    Parsey, Ramin V.
    EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING, 2007, 34 (07) : 1050 - 1060
  • [9] Synthesis and in vivo evaluation of [O-methyl-11C] (2R,4R)-4-hydroxy-2-[2-[2-[2-(3-methoxy)phenyl]ethyl]phenoxy]ethyl-1-methylpyrrolidine as a 5-HT2A receptor PET ligand
    Kumar, J. S. Dileep
    Prabhakaran, Jaya
    Erlandsson, Kjell
    Majo, Vattoly J.
    Simpson, Norman R.
    Pratap, Mali
    Van Heertum, Ronald L.
    Mann, J. John
    Parsey, Ramin V.
    NUCLEAR MEDICINE AND BIOLOGY, 2006, 33 (04) : 565 - 574
  • [10] Synthesis and in vivo evaluation of [O-methyl-11C] N-[3,5-dichloro-2-(methoxy)phenyl]-4-(methoxy)-3-(1-piperazinyl)benzenesulfonamide as an imaging probe for 5-HT6 receptors
    Liu, Fei
    Majo, Vattoly J.
    Prabhakaran, Jaya
    Milak, Matthew S.
    Mann, J. John
    Parsey, Ramin V.
    Kumar, J. S. Dileep
    BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (17) : 5255 - 5259