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Synthesis of deuterium-labeled 1-(4-methoxybenzyl)-3-(5-nitrothiazol-2-yl)urea (AR-A014418) as an internal standard for LC–MS analysis

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Abstract

AR-A014418, 1-(4-methoxybenzyl)-3-(5-nitrothiazol-2-yl)urea is a potential drug with potent activities against cancer cell, nociceptive pain and neurodegenerative disorders. In this paper, the stable deuterium-labeled [2H3]AR-A014418 was synthesized in seven steps with 21% overall yield starting from the commercially available [2H4]methanol, p-hydroxybenzaldehyde and 2-amino-5-nitrothiazole. The chemical and isotope purity of the title compound were over 99% and 98%, respectively. This labeled [2H3]AR-A014418 can be used as an internal standard for LC–MS analysis in drug absorption, distribution and other pharmacokinetics studies.

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Acknowledgements

We are grateful for financial support from the Applied Basic Research and Development Programs of the Science and Technology Foundation of Ya’an (2017YYJSKF15).

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Authors and Affiliations

  1. School of Pharmacy and Medical Laboratory Science, Ya’an Polytechnic College, Ya’an, 625000, Sichuan, China

    Dawei Liang & Yueqiu Wang

  2. Shandong Huijing Biopharmaceutical Technology Co., Ltd., 1 Lutai Road, Zibo, 255000, Shandong, China

    Tingchang Yan & Zhaoyang Wang

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  1. Dawei Liang
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  2. Yueqiu Wang
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Correspondence to Dawei Liang.

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Liang, D., Wang, Y., Yan, T. et al. Synthesis of deuterium-labeled 1-(4-methoxybenzyl)-3-(5-nitrothiazol-2-yl)urea (AR-A014418) as an internal standard for LC–MS analysis. J Radioanal Nucl Chem 325, 217–222 (2020). https://doi.org/10.1007/s10967-020-07227-0

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  • DOI: https://doi.org/10.1007/s10967-020-07227-0

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