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.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270573PMC
http://dx.doi.org/10.3390/molecules18078028DOI Listing

Publication Analysis

Top Keywords

regioselective dephosphorylation
8
mechanistic studies
4
studies regioselective
4
dephosphorylation phosphate
4
phosphate prodrugs
4
prodrugs facile
4
facile synthesis
4
synthesis antitumor
4
antitumor phosphorylated
4
phosphorylated 2-phenyl-67-methylenedioxy-1h-quinolin-4-one
4

Similar Publications

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!