646522-20-5

Upstream product

• 591-50-4 iodobenzene 
• 188117-96-6 2',3',5'-tri-O-(tert-butyldimethylsilyl)-6-vinylnebularine 
• 84765-96-8 6-chloro-9-(2,3,5-tris-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl)-9H-purine 
• 1233765-82-6 6-(phenylethynyl)-9-(O,O,O-tris(tert-butyldimethylsilyl)-β-D-ribofuranosyl)-9H-purine 

Relevant academic research and scientific papers

Cytotoxic activity of 6-alkynyl- and 6-alkenylpurines

6-Alkynyl- and 6-alkenylpurines have been screened for cytotoxic activity against a human chronic myelogenous leukemia cell line; K-562 cells using a [3H]-thymidine incorporation assay. Most alkynes displayed cytotoxicity comparable to, or better than, the known anticancer drugs 6-mercaptopurine and fludarabine. The 6-alkenylpurines, which are promising plant growth stimulators and 15-lipoxygenase inhibitors, exhibited only low toxicity.

Synthesis of (E)-6-alkenylpurines via Pd-catalyzed stannation/ protodestannation tandem process of alkynylpurines

A methodology for the synthesis of (E)-6-alkenylpurines, starting from 6-iodopurines, based on a Pd-catalyzed stannation/protodestannation protocol, is described. The alkynylation reactions were catalyzed by Pd(OAc) 2/PPh3 in acetonitrile. The Pd-catalyzed stannation itself provided a mixture of Z regioisomers but following protodestannation using TFA induces Z to E isomerization giving (E)-6-alkenylpurines. The reactivity of other 2-and 8-alkynyl purines has also been studied.