218431-10-8Relevant articles and documents
Design, synthesis, and anticancer activity of C8-substituted-4′-thionucleosides as potential HSP90 inhibitors
Qu, Shuhao,Mulamoottil, Varughese A.,Nayak, Akshata,Ryu, Seungyeon,Hou, Xiyan,Song, Jayoung,Yu, Jinha,Sahu, Pramod K.,Zhao, Long Xuan,Choi, Sun,Lee, Sang Kook,Jeong, Lak Shin
, p. 3418 - 3428 (2016)
A series of C8-substituted-4′-thioadenosine analogs 3a–3g, 15, and 17 and their truncated derivatives 4a–4j, 23–25, and 27 have been successfully synthesized from D-ribose and D-mannose, respectively, employing Pummerer type or Vorbrüggen condensation reactions and the functionalization at the C8-position of nucleobase via Stille coupling or nucleophilic aromatic substitution reactions as key steps. All the synthesized compounds were assayed for their HSP90 inhibitory activity, but they were found to be inactive up to 100 μM. However, the 8-iodo derivatives 15, 17, and 27 exhibited potent anticancer activity, indicating that different mechanism of action might be involved in their biological activity.
Regioselective Sonogashira cross-coupling reactions of 6-chloro-2,8-diiodo- 9-THP-9H-purine with alkyne derivatives
Ibrahim, Nada,Chevot, Franciane,Legraverend, Michel
supporting information; experimental part, p. 305 - 307 (2011/02/26)
Lithiation of 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine with LiTMP, gave access to 6-chloro-2,8-dihalogenated purine derivatives. In particular, the 6-chloro-2,8-diiodopurine derivative is an interesting new intermediate which gave regioselectively various 2-alkynylated compounds or 2,8-dialkynylated purines by using an excess of alkyne.
