828935-20-2Relevant academic research and scientific papers
A new synthetic route to (North)-methanocarba nucleosides designed as A3 adenosine receptor agonists
Joshi, Bhalchandra V.,Hyung, Ryong Moon,Fettinger, James C.,Marquez, Victor E.,Jacobson, Kenneth A.
, p. 439 - 447 (2007/10/03)
(Chemical Equation Presented) Activation of the A3 adenosine receptor (AR) is associated with cerebroprotective, cardioprotective, and anticancer effects. Among potent and selective A3 AR agonists are novel methanocarba adenosine analogues in which the conformation of a pseudo-ribose moiety is locked in the North (N) hemisphere of the pseudorotational cycle. 5′-Uronamide (N)-methanocarba nucleosides, such as MRS1898 and MRS2346, are examples of full agonists of the human A3 AR. An improved convergent approach from easily accessible 2,3-O-isopropylidene- D-erythrose (2b), and the combination of a strategic intramolecular cyclopropanation step plus the acid-catalyzed isomerization of an isopropylidene group, provided a suitable pseudosugar precursor (23) for the synthesis of MRS1898, MRS2346, and related analogues. This new synthetic route uses readily available building blocks and opens the way for the preparation of a variety of targets on a reasonable scale.
Recent advances in the synthesis of conformationally locked nucleosides and their success in probing the critical question of conformational preferences by their biological targets
Choi, Yongseok,Moon, Hyung R.,Yoshimura, Yuichi,Marquez, Victor E.
, p. 547 - 557 (2007/10/03)
The present work describes some recent approaches to the syntheses of three classes of locked-North nucleosides: β-D-ribo-, β-D-deoxyribo-, and β-D-dideoxy-ribonucleosides. The method developed for the latter class permitted access to a novel bicyclo[3.1.
