181475-59-2Relevant academic research and scientific papers
Convenient syntheses of 6-methylpurine and related nucleosides
Hassan,Abou-Elkair,Montgomery,Secrist III
, p. 1123 - 1134 (2000)
Efficient methods for the synthesis of 6-methylpurine (3), 9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methylpurine (8), and 6-methyl-9-β-D-ribofuranosylpurine (5) are described. Methodology involving the (Ph3P)4Pd catalyzed cross-coupling reaction of CH3ZnBr with several different 6-chloropurine derivatives is described in high yield. This methodology now provides a facile and high-yielding synthesis of 8, which is needed in significant amounts for studies in cancer gene therapy.
Gene therapy of cancer: activation of nucleoside prodrugs with e. colipurine nucleoside phosphorylase
Secrist III, John A.
, p. 745 - 757 (2007/10/03)
During the last few years, many gene therapy strategies have been developed for various disease targets. The development of anticancer gene therapy strategies to selectively generate cytotoxic nucleoside or nucleotide analogs is an attractive goal. One such approach involves the delivery of herpes simplex virus thymidine kinase followed by the acyclic nucleoside analog ganciclovir. We have developed another gene therapy methodology for the treatment of cancer that has several significant attributes. Specifically, our approach involves the delivery of E. coli purine nucleoside phosphorylase, followed by treatment with a relatively non-toxic nucleoside prodrug that is cleaved by the enzyme to a toxic compound. .This presentation describes the concept, details our search for suitable prodrugs, and summarizes the current biological data. Copyright
Stereoselective synthesis of 6-methyl-9-(2-deoxy-β-D-erythro- pentofuranosyl)purine
Anderson-McKay, Janet E.,Both, Gerald W.,Simpson, Gregory W.
, p. 1307 - 1313 (2007/10/03)
The coupling of the sodium salt of 6-methylpurine with 2-deoxy-3,5-di- O-p-toluoyl-α-D-erythro-pentofuranosyl chloride in acetonitrile gives the di-O-p-toluoyl protected 9-β nucleoside regio- and stereo-selectively in good yield. Methoxide deprotection followed by preparative hplc then affords pure 6-methyl-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine.
