Efficient diastereoselective synthesis of a new class of azanucleosides: 2′-homoazanucleosides

Abstract

a b s t r a c tAzanucleosides, sugar-modified nucleoside analogues containing a 4 0 nitrogen atom, have shown a lot of therapeutic potential, e.g. as anti-cancer and antiviral agents. We report the synthesis of a series of 2'homoazanucleosides, in which the nucleobase is attached to the 2'-position of the pyrrolidine ring via a methylene linker. A suitable orthogonally protected iminosugar was synthesized by ring closing metathesis and dihydroxylation as key steps and further converted to a series of 8 nucleoside analogues through Mitsunobu reaction with suitably protected nucleobases. The 5 0 position of the adenine analogue was then further derivatized with thiols to afford 2 additional compounds. The final compounds were evaluated for biological activity.

Synthetic Modifications of a Pb2+-Sensor Acridono-Crown Ether for Covalent Attachment and Their Effects on Selectivity

“…The revised synthetic route can be seen in Scheme 4. Reported intermediate 31 was synthesized starting from mannitol (30) according to a reported procedure [28][29][30]. The former was treated with monotosyl-monotrityl triethylene glycol 32 to provide ditrityl 33, but this coupling did not succeed.…”

Membrane-Active Thermoresponsive Block Copolymers Containing a Diacylglycerol-Based Segment: RAFT Synthesis, Doxorubicin Encapsulation, and Evaluation of Cytotoxicity against Breast Cancer Cells

“…In turn, due to the unsaturated bonds in the oleic acid derivative, the hydroxyl function (3b) was obtained using BCl 3 in DCM at −78 °C. 26,27 Importantly, no side reactions of the oleate double bonds were observed, confirming the effectiveness of the synthetic procedure. The last-step reaction with acryloyl chloride at 0 °C led to the formation of the original diglyceride-based monomers (4a, 4b).…”

Recent Advances in the Chemical Synthesis and Evaluation of Anticancer Nucleoside Analogues

“…Azanucleosides were originally defined as nucleoside analogues where the furanosyl oxygen is replaced by nitrogen, however this group of analogues has been extended to include nucleosides where the resultant pyrrolidine core has been replaced by other nitrogen containing rings, including heterocycles, heterotricycles and acyclic nitrogen-containing nucleosides [16,17]. This class of compound have proven successful in the treatment of cancer [18] and have also been established as having antiviral and antibacterial properties [19].…”