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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 3.0).

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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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