合成有潛力做為正子斷層掃描腫瘤造影劑的氟取代蒽醌類化合物

劉惠賢

doi:10.6342/NTU.2010.02247

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合成有潛力做為正子斷層掃描腫瘤造影劑的氟取代蒽醌類化合物

Synthesis of Fluoro-substituted Anthraquinones as Potential Tumor Imaging Agents for Positron Emission Tomography

劉惠賢 , Masters　　Advisor：忻凌偉　　

繁體中文 DOI： 10.6342/NTU.2010.02247

氟取代胺基蒽醌類化合物；正子斷層掃描； Fluror-substituted Anthraquinones ； PET

Abstract │ Reference (36) │ Altmetrics

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Based on the results of a series of studies on the pharmacological activity of fluoroaminoqnthraquinones in our laboratory, fluorine-18 labeled compound 48 was selected to be synthesized for the application of positron emission tomography in this study. The synthetic principle is to introduce fluorine-18 at the terminal step of the whole synthetic route and to optimize the total reaction time, as to minimize the decay of radioactive fluorin-18. Theoretically, this can be achieved by two synthetic methods: direct nucleophilic substitution through introducing fluorine-18 into precursor 2 and indirect substitution through introducing fluoring-18 labeled prosthetic group into precursor 1 to get the fluorine-18 labeled target compound 48. Precursor 1 (49), precursor 2 (39) and fluorination standard compound 38 and 48 were successfully synthesized in this study. First, the terminal hydroxyl group of commercial available starting material, N-(3-hydroxylpropyl)ethylenediamine, was protected with TBDMS protecting group and then bound to the Leucoquinizarin by condensation and oxidation reactions. The amino groups (R1 and R3) were protected by triphenylmethyl protecting group and then the TBDMS protecting group was removed by potassium fluoride and Kryptofix 222. Eventually, precursor 39 was obtain by Mesylation. Whereas for precursor 49, standard compound 48 and standard compound 38, the amino group (R2) in ethylenediamine was protected by Teoc protecting group and bound to Leucoquinizarin by condensation and oxidation reactions. Then, then the amino group (R1) was protected by triphenylmethyl protecting group and the Teoc protecting group was removed by potassium fluoride and Kryptofix 222 to get precursor 49. The standard compound 48, yield: 26%, was obtained from precursor 49 by nucleophilic substitution with the prosthetic group, 3-fluoropropyl-p-toluene sulfonate. Finally, the amino group in standard compound 48 was protected by triphenylmethyl protecting group to gain fluorination standard compound 38.

Reference ( 36 ) 〈TOP〉

1.Shiue, C. Y.; Welch, M. J. Update on PET radiopharmaceuticals: life beyond fluorodeoxyglucose. Radiologic Clinics of North America. 2004, 42, 1033-1053.
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2.Fowler, J. S.; Ding, Y. S.; Volkow, N. D. Radiotracers for Positron Emission Tomography Imaging. Seminars in Nuclear Medicine. 2003, 23, 14-27.
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3.Vallabhajosula, S. 18F-Labelled Positron Emission Tomographic Radiopharmaceuticals in Oncology: An Overview of Radiochemistry and Mechanisms of Tumor Location. Seminars in Nuclear Medicine. 2007, 37, 400-419.
連結：
4.Wood, K. A.; Hoskin, P. J.; Saunders, M. I. Positron Emission Tomography in Oncology: A Review. Clinical Oncology. 2007, 19, 237-255.
連結：
5.Weber, W. A. Positron Emission Tomography As an Imaging Biomarker. Journal of Clinical Oncology. 2008, 24, 3282-3292.
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