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

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,* email and 1,4,* email
Received: 13 May 2013; in revised form: 5 June 2013 / Accepted: 1 July 2013 / Published: 8 July 2013
(This article belongs to the Section Medicinal Chemistry)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: 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
PDF Full-text Download PDF Full-Text [607 KB, uploaded 18 June 2014 20:08 CEST]

Export to BibTeX |
EndNote


MDPI and ACS Style

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.

AMA Style

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(7):8028-8045.

Chicago/Turabian Style

Cheng, Yung-Yi; Liu, Chin-Yu; Huang, Li-Jiau; Huang, Chi-Hung; Lee, Kuo-Hsiung; Lin, Cheng-Tung; Kuo, Sheng-Chu. 2013. "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 18, no. 7: 8028-8045.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert