95740-17-3

Basic information

• Product Name: 4-amino-5-ethyl-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• Synonyms: 4-amino-5-ethyl-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;2(1H)-Pyrimidinone, 4-amino-1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-ethyl-
• CAS NO: 95740-17-3
• Molecular Formula: C11H16FN3O4
• Molecular Weight: 273.2608
• Mol File: 95740-17-3.mol

Chemical Properties

• Boiling Point: 499.2 °C at 760 mmHg
• Flash Point: 255.7 °C
• Appearance: /
• Density: 1.65 g/cm³
• Vapor Pressure: 4.68E-12mmHg at 25°C
• Refractive Index: 1.655
• CAS DataBase Reference: 4-amino-5-ethyl-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-amino-5-ethyl-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one(95740-17-3)
• EPA Substance Registry System: 4-amino-5-ethyl-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one(95740-17-3)

Safety Data

• Hazardous Substances Data: 95740-17-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H16FN3O4/c1-2-5-3-15(11(18)14-9(5)13)10-7(12)8(17)6(4-16)19-10/h3,6-8,10,16-17H,2,4H2,1H3,(H2,13,14,18)/t6-,7+,8-,10-/m1/s1

Upstream product

• 83546-42-3 FEAU 
• 56632-83-8 1-(2-fluoro-2-deoxy-β-D-arabinofuranosyl)cytosine 
• 95740-19-5 C₂₅H₂₃FN₂O₆S 
• 95740-20-8 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-4-thio-5-ethyluracil 
• 95740-18-4 1-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-D-arabinofuranofuranosyl)-5-ethyluracil 
• 95740-21-9 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-4-(methylthio)-5-ethyl-2(1H)-pyrimidinone 
• 95740-16-2 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-vinylcytosine 

Relevant articles and documents

Discovery of novel 5-(ethyl or hydroxymethyl) analogs of 2′-'up' fluoro (or hydroxyl) pyrimidine nucleosides as a new class of Mycobacterium tuberculosis, Mycobacterium bovis and Mycobacterium avium inhibitors

Discovery of novel antimycobacterial compounds that work on distinctive targets and by diverse mechanisms of action is urgently required for the treatment of mycobacterial infections due to the emerging global health threat of tuberculosis. We have identified a new class of 5-ethyl or hydroxy (or methoxy) methyl-substituted pyrimidine nucleosides as potent inhibitors of Mycobacterium bovis, Mycobacterium tuberculosis (H37Ra, H37Rv) and Mycobacterium avium. A series of 2′-'up' fluoro (or hydroxy) nucleosides (1, 2, 4-6, 9, 10, 13, 16, 18, 21, 24) was synthesized and evaluated for antimycobacterial activity. Among 2′-fluorinated compounds, 1-(3-bromo-2,3-dideoxy-2-fluoro- β-d-arabinofuranosyl)-5-ethyluracil (13) exhibited promising activity against M. bovis and Mtb alone, and showed synergism when combined with isoniazid. The most active compound emerging from these studies, 1-(β-d-arabinofuranosyl)-4-thio-5-hydroxymethyluracil (21) inhibited Mtb (H37Ra) (MIC50 = 0.5 μg/mL) and M. bovis (MIC50 = 0.5 μg/mL) at low concentrations, and was ten times more potent against Mtb (H37Ra) than cycloserine (MIC50 = 5.0 μg/mL), a second line drug. It also showed an additive effect when combined with isoniazid. Compound 21 retained sensitivity against a rifampicin-resistant (H37Rv) strain of Mtb (MIC50 = 1 μg/mL) at concentrations similar to that for a rifampicin-sensitive (H37Rv) strain, suggesting that it has no cross-resistance to a first-line anti-TB drug. In addition, the replication of M. avium was also inhibited by 21 (MIC50 = 10 μg/mL). No cellular toxicity of 13 or 21 was observed up to the highest concentration tested (CC50 > 100 μg/mL). These observations offer promise for a new drug treatment regimen to augment and complement the current chemotherapy of TB.

Nucleosides. 133. Synthesis of 5-alkenyl-1-(2-deoxy-2-fluoro- β-D-arabinofuranosyl)cytosines and related pyrimidine nucleosides as potential antiviral agents

The synthesis of 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)cytosines with a halovinyl (8 and 9) or vinyl (10) substituent at C-5 was accomplished from the corresponding 5-iodo (FIAC, 1) and/or 5-chloromercuri (5) nucleoside analogues with use of Li2/

5-Substituted 1-(2'-Deoxy-2'-substituted-β-D-arabinofuranosyl)pyrimidine nucleosides

Pyrimidine nucleosides exhibiting anti-viral and anti-tumor effects have the formula STR1 wherein A is OR3, SR3, NR3 R4 or NHacyl wherein R3 and R4 are the same or different and are hydroge