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Molecules 2013, 18(7), 8028-8045; doi:10.3390/molecules18078028

Mechanistic Studies on Regioselective Dephosphorylation of Phosphate Prodrugs during a Facile Synthesis of Antitumor Phosphorylated 2-Phenyl-6,7-methylenedioxy-1H-quinolin-4-one

1, 1, 1, 2, 3,4, 5,*  and 1,4,*
1 Graduate Institute of Pharmaceutical Chemistry, China Medical University, No.91 Hsueh-Shih Road, Taichung, 40402, Taiwan 2 Graduate School of Biotechnology, Hung Kuang University, Taichung, No. 1018, Sec. 6, Taiwan Boulevard, Shalu District, Taichung, 43302, Taiwan 3 Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC 27599, USA 4 Chinese Medicine Research and Development Center, China Medical University and Hospital, 2 Yuh-Der Road, Taichung, 40447, Taiwan 5 Department of Chemistry, Science College, Tunghai University, No.1727, Sec.4, Taiwan Boulevard, Xitun District, Taichung, 40704, Taiwan
* Authors to whom correspondence should be addressed.
Received: 13 May 2013 / Revised: 5 June 2013 / Accepted: 1 July 2013 / Published: 8 July 2013
(This article belongs to the Section Medicinal Chemistry)
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Phosphorylation of 2-(3-hydroxy-5-methoxyphenyl)-6,7-methylenedioxy-1H-quinolin-4-one (1) afforded diphosphate 2. We found that, upon treatment with methanol under mild conditions, 2 can undergo facile and highly regioselective dephosphorylation to give the monophosphate 3, with a phosphate group remaining on the phenyl ring. The details of the dephosphorylation process were postulated and then probed by LC-MS and HPLC analyses. Furthermore, as a preliminary study, the water soluble monophosphate prodrug 4 was tested for antitumor activity against a MCF-7 xenograft nude mice model.
Keywords: MCF-7; prodrugs; dephosphorylation; antitumor activity MCF-7; prodrugs; dephosphorylation; antitumor activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Cheng, Y.-Y.; Liu, C.-Y.; Huang, L.-J.; Huang, C.-H.; Lee, K.-H.; Lin, C.-T.; Kuo, S.-C. Mechanistic Studies on Regioselective Dephosphorylation of Phosphate Prodrugs during a Facile Synthesis of Antitumor Phosphorylated 2-Phenyl-6,7-methylenedioxy-1H-quinolin-4-one. Molecules 2013, 18, 8028-8045.

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