144874-60-2Relevant academic research and scientific papers
Diastereoselective Flexible Synthesis of Carbocyclic C-Nucleosides
Maier, Luká?,Khirsariya, Prashant,Hylse, Ond?ej,Adla, Santosh Kumar,?ernová, Lenka,Poljak, Michal,Kraj?ovi?ová, Soňa,Weis, Erik,Drápela, Stanislav,Sou?ek, Karel,Paruch, Kamil
, p. 3382 - 3402 (2017)
Carbocyclic C-nucleosides are quite rare. Our route enables flexible preparation of three classes of these nucleoside analogs from common precursors-properly substituted cyclopentanones, which can be prepared racemic (in six steps) or optically pure (in ten steps) from inexpensive norbornadiene. The methodology allows flexible manipulation of individual positions around the cyclopentane ring, namely highly diastereoselective installation of carbo- and heterocyclic substituents at position 1′, orthogonal functionalization of position 5′, and efficient inversion of stereochemistry at position 2′. Newly prepared carbocyclic C-analog of tubercidine, profiled in MCF7 (breast cancer) and HFF1 (human foreskin fibroblasts) cell cultures, is less potent than tubercidine itself, but more selectively toxic toward the tumorigenic cells.
New carbocyclic nucleosides: Synthesis of carbocyclic pseudoisocytidine and its analogs
Maier, Luká?,Hylse, Ond?ej,Ne?as, Marek,Trbu?ek, Martin,Ytre-Arne, Mari,Dalhus, Bj?rn,Bjor?s, Magnar,Paruch, Kamil
, p. 3713 - 3716 (2014)
Cyclopentane-containing nucleoside analogs with a CC connection between the (heterocyclic) base and the carbocyclic scaffold are quite rare. Herein, we report the synthesis of previously unknown racemic carbocyclic pseudoisocytidine and its analogs, which
Synthesis of pseudo-Ribofuranoses by Stereocontrolled Reactions on 4-Hydroxycyclopent-2-enylmethanol Derivatives
Shoberu, Karoline A.,Roberts, Stanley M.
, p. 2419 - 2426 (2007/10/02)
The diol 3 is a major product formed from a Prins reaction on cyclopentadiene and was readily converted into the derivatives 4-7.The latter compounds were obtained in states of high optical purity by using both enzyme-catalysed hydrolysis and esterificati
