Synthesis of 2,6-difluoro-N-(3-[11C]methoxy-1H-pyrazolo[3,4-b]pyridine-5-yl)-3-(propylsulfonamidio)benzamide as a new potential PET agent for imaging of B-RafV600E in cancers
Тип публикации: Journal Article
Дата публикации: 2013-03-01
scimago Q2
wos Q2
БС2
SJR: 0.472
CiteScore: 5.1
Impact factor: 2.2
ISSN: 0960894X, 14643405
PubMed ID:
23294704
Organic Chemistry
Drug Discovery
Biochemistry
Molecular Biology
Pharmaceutical Science
Clinical Biochemistry
Molecular Medicine
Краткое описание
Synthesis of a new PET agent 2,6-difluoro- N -(3-[ 11 C]methoxy-1 H -pyrazolo[3,4- b ]pyridine-5-yl)-3-(propylsulfonamidio)benzamide for imaging of cancer B-Raf V600E is presented. The authentic standard 2,6-difluoro- N -(3-methoxy-1 H -pyrazolo[3,4- b ]pyridine-5-yl)-3-(propylsulfonamidio)benzamide was synthesized from 2,6-difluorobenzoic acid and 3-amino-5-hydroxypyrazole in 9 steps with 1% overall chemical yield. Direct desmethylation of the reference standard with TMSCl/NaI gave the precursor 2,6-difluoro- N -(3-hydroxy-1 H -pyrazolo[3,4- b ]pyridine-5-yl)-3-(propylsulfonamidio)benzamide for radiolabeling in 70% yield. The target tracer 2,6-difluoro- N -(3-[ 11 C]methoxy-1 H -pyrazolo[3,4- b ]pyridine-5-yl)-3-(propylsulfonamidio)benzamide was prepared from the precursor with [ 11 C]CH 3 OTf through O -[ 11 C]methylation and isolated by HPLC combined with SPE in 40–50% decay corrected radiochemical yields with 370–740 GBq/μmol specific activity at end of bombardment (EOB).
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Wang M. et al. Synthesis of 2,6-difluoro-N-(3-[11C]methoxy-1H-pyrazolo[3,4-b]pyridine-5-yl)-3-(propylsulfonamidio)benzamide as a new potential PET agent for imaging of B-RafV600E in cancers // Bioorganic and Medicinal Chemistry Letters. 2013. Vol. 23. No. 4. pp. 1017-1021.
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Wang M., Gao M., Miller K., ZHENG Q. Synthesis of 2,6-difluoro-N-(3-[11C]methoxy-1H-pyrazolo[3,4-b]pyridine-5-yl)-3-(propylsulfonamidio)benzamide as a new potential PET agent for imaging of B-RafV600E in cancers // Bioorganic and Medicinal Chemistry Letters. 2013. Vol. 23. No. 4. pp. 1017-1021.
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TY - JOUR
DO - 10.1016/j.bmcl.2012.12.027
UR - https://doi.org/10.1016/j.bmcl.2012.12.027
TI - Synthesis of 2,6-difluoro-N-(3-[11C]methoxy-1H-pyrazolo[3,4-b]pyridine-5-yl)-3-(propylsulfonamidio)benzamide as a new potential PET agent for imaging of B-RafV600E in cancers
T2 - Bioorganic and Medicinal Chemistry Letters
AU - Wang, Min
AU - Gao, Mingzhang
AU - Miller, Kathy
AU - ZHENG, QI-HUANG
PY - 2013
DA - 2013/03/01
PB - Elsevier
SP - 1017-1021
IS - 4
VL - 23
PMID - 23294704
SN - 0960-894X
SN - 1464-3405
ER -
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@article{2013_Wang,
author = {Min Wang and Mingzhang Gao and Kathy Miller and QI-HUANG ZHENG},
title = {Synthesis of 2,6-difluoro-N-(3-[11C]methoxy-1H-pyrazolo[3,4-b]pyridine-5-yl)-3-(propylsulfonamidio)benzamide as a new potential PET agent for imaging of B-RafV600E in cancers},
journal = {Bioorganic and Medicinal Chemistry Letters},
year = {2013},
volume = {23},
publisher = {Elsevier},
month = {mar},
url = {https://doi.org/10.1016/j.bmcl.2012.12.027},
number = {4},
pages = {1017--1021},
doi = {10.1016/j.bmcl.2012.12.027}
}
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MLA
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Wang, Min, et al. “Synthesis of 2,6-difluoro-N-(3-[11C]methoxy-1H-pyrazolo[3,4-b]pyridine-5-yl)-3-(propylsulfonamidio)benzamide as a new potential PET agent for imaging of B-RafV600E in cancers.” Bioorganic and Medicinal Chemistry Letters, vol. 23, no. 4, Mar. 2013, pp. 1017-1021. https://doi.org/10.1016/j.bmcl.2012.12.027.