117134-30-2

Usage

InChI:InChI=1/C11H14N2O5/c12-11(17)6-3-1-2-5(13-6)10-9(16)8(15)7(4-14)18-10/h1-3,7-10,14-16H,4H2,(H2,12,17)/t7-,8-,9-,10+/m1/s1

Upstream product

• 626-05-1 2,6-Dibromopyridine 
• 1203651-68-6 1β-[6-(carbamoyl)pyridin-2-yl]-1-deoxy-2,3,5-tri-O-(t-butyldimethylsilyl)-D-ribofuranose 
• 117432-65-2 methyl 6-(2,4:3,5-di-O-benzylidene-D-altro-pentitol-1-yl)picolinate 
• 117152-83-7 6-(2,4:3,5-di-O-benzylidene-D-altro-pentitol-1-yl)picolinamide 
• 117134-22-2 6-(2,4:3,5-di-O-benzylidene-D-altro-pentitol-1-yl)-2-bromopyridine 
• 107436-58-8 2,4:3,5-di-O-benzylidene-D-aldehydo-ribose 
• 115078-78-9 6-(2,3:4,5-di-O-isopropylidene-D-altro-pentitol-1-yl)-2-bromopyridine 
• 117152-84-8 6-(2,4:3,5-di-O-benzylidene-1-O-mesyl-D-altro-pentitol-1-yl)picolinamide 

Relevant academic research and scientific papers

Synthesis of Isosteric Analogues of Nicotinamide Adenine Dinucleotide Containing C-Nucleotide of Nicotinamide or Picolinamide

Two isosteric analogues of nicotinamide adenine dinucleotide, C-NAD (11) and C-PAD (12), in which the nicotinamide riboside portion is replaced by a C-nucleoside, were synthesized from 5-(β-D-ribofuranosyl)nicotinamide (7) and 6-(β-D-ribofuranosyl)picolinamide (8), respectively.Nucleoside 7 was prepared from the 2,3-O-isopropylidene-5-O-(tetrahydropyranyl)-D-ribonolactone (13) and 3-cyano-5-lithiopyridine as reported earlier.Nucleoside 8 was obtained by conversion of the bromo function of the 6-(2,3:4,5-di-O-isopropylidene-D-altro-pentitol-1-yl)-2-bromopyridine (14)into a carboxamido group followed by mesylation of the anomeric hydroxyl group to give derivative 18.Treatment of 18 with CF3COOH/CHCl3 caused deisopropylidenation with simultaneous cyclization into the desired 6-(β-D-ribofuranosyl)picolinamide (8).NAD analogues, C-NAD (11) and C-PAD (12), were synthesized by imidazole-catalyzed coupling of the corresponding 5'-monophosphates of 7 and 8 with the adenosine-5'-monophosphate.Dinucleotide 11 was found to inhibit the proliferation of L1210 cells (IC50 = 7 μM) and to be a good competitive inhibitor of inosine monophosphate dehydrogenase (IMPDH, ID50 = 20 μM) as well as bovine glutamate dehydrogenase (GDH, Ki = 15 μM).Interestingly, C-NAD (11) caused extremely potent noncompetitive inhibition of horse liver alcohol dehydrogenase (ADH, Ki = 1.1 nM), whereas C-PAD (12) was found to be a much less potent competitive inhibitor (Ki = 20 μM) of ADH.

A general and efficient synthesis of pyridin-2-yl C-ribonucleosides bearing diverse alkyl, aryl, amino, and carbamoyl groups in position 6

(Chemical Equation Presented) An efficient and practical methodology of preparation of 6-substituted pyridin-2-yl C-ribonucleosides was developed. A one-pot two-step addition of 2-lithio-6-bromopyridine to TBS-protected ribonolactone followed by acetylation gave 1β-(6-bromopyridin-2-yl)-1-O- acetyl-2,3,5-tri-O-(tertbutyldimethylsilyl)-D-ribofuranose in high yield. Its reduction with Et3SiH and BF3·Et2O afforded the desired TBS-protected 6-bromopyridine C-ribonucleoside as pure β-anomer in good overall yield of 63%. This intermediate was then subjected to a series of palladium catalyzed cross-coupling reactions, aminations and aminocarbonylations to give a series of protected 1β-(6-alkyl-, 6-aryl-, 6- amino-, and 6-carbamoylpyridin-2-yl)-C-ribonucleosides. Deprotection of silylated nucleosides by Et3N·3HF gave a series of title free C-ribonucleosides (12 examples).