Novel synthetic route to the C-nucleoside, 2-deoxy benzamide riboside

TY - JOUR

T1 - Novel synthetic route to the C-nucleoside, 2-deoxy benzamide riboside

AU - Midtkandal, Rebecca R.

AU - Redpath, Philip

AU - Trammell, Samuel A J

AU - MacDonald, Simon J F

AU - Brenner, Charles

AU - Migaud, Marie E.

PY - 2012/8/15

Y1 - 2012/8/15

N2 - 2-Deoxy-C-nucleosides are a subcategory of C-nucleosides that has not been explored extensively, largely because the synthesis is less facile. Flexible synthetic procedures giving access to 2-deoxy-C-nucleosides are therefore of interest. To exemplify the versatility and highlight the limitations of a synthetic route recently developed to that effect, the first synthesis of 2-deoxy benzamide riboside is reported. Biological properties of this novel C-nucleoside are also discussed.

AB - 2-Deoxy-C-nucleosides are a subcategory of C-nucleosides that has not been explored extensively, largely because the synthesis is less facile. Flexible synthetic procedures giving access to 2-deoxy-C-nucleosides are therefore of interest. To exemplify the versatility and highlight the limitations of a synthetic route recently developed to that effect, the first synthesis of 2-deoxy benzamide riboside is reported. Biological properties of this novel C-nucleoside are also discussed.

KW - Benzamide riboside

KW - C-Nucleoside

KW - Inosine monophosphate dehydrogenase

KW - Intramolecular cyclisation

KW - Nicotinamide adenine dinucleotide

UR - http://www.scopus.com/inward/record.url?scp=84864411406&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2012.06.069

DO - 10.1016/j.bmcl.2012.06.069

M3 - Journal article

C2 - 22795628

AN - SCOPUS:84864411406

SN - 0960-894X

VL - 22

SP - 5204

EP - 5207

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 16

ER -