117134-30-2

Basic information

• Product Name: 6-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyridine-2 -carboxamide
• Synonyms: 6-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyridine-2 -carboxamide;6-(beta-ribofuranosyl)picolinamide
• CAS NO: 117134-30-2
• Molecular Formula: C11H14N2O5
• Molecular Weight: 254.24
• Mol File: 117134-30-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 581.7°Cat760mmHg
• Flash Point: 305.6°C
• Appearance: /
• Density: 1.509g/cm³
• Vapor Pressure: 2.25E-14mmHg at 25°C
• Refractive Index: 1.643
• CAS DataBase Reference: 6-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyridine-2 -carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 6-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyridine-2 -carboxamide(117134-30-2)
• EPA Substance Registry System: 6-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyridine-2 -carboxamide(117134-30-2)

Safety Data

• Hazardous Substances Data: 117134-30-2(Hazardous Substances Data)

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

• 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 
• 626-05-1 2,6-Dibromopyridine 
• 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 articles and documents

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.

Nucleosides. CXLVIII. Synthesis of 6-(β-D-ribofuranosyl)picolinamide. A novel C-nucleoside from D-ribonolactone

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