110289-24-2

Basic information

• Product Name: 2-amino-1,9-dihydro-9-(2-fluoro-3-hydroxy-4-(hydroxymethyl)cyclopentyl)-6H-purin-6-one
• Synonyms: 2-amino-1,9-dihydro-9-(2-fluoro-3-hydroxy-4-(hydroxymethyl)cyclopentyl)-6H-purin-6-one
• CAS NO: 110289-24-2
• Molecular Formula: C11H14 F N5 O3
• Molecular Weight: 283.26
• Mol File: 110289-24-2.mol

Chemical Properties

• Boiling Point: 665.7°Cat760mmHg
• Flash Point: 356.4°C
• Appearance: /
• Density: 2.01g/cm³
• Vapor Pressure: 1.26E-18mmHg at 25°C
• Refractive Index: 1.853
• CAS DataBase Reference: 2-amino-1,9-dihydro-9-(2-fluoro-3-hydroxy-4-(hydroxymethyl)cyclopentyl)-6H-purin-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-1,9-dihydro-9-(2-fluoro-3-hydroxy-4-(hydroxymethyl)cyclopentyl)-6H-purin-6-one(110289-24-2)
• EPA Substance Registry System: 2-amino-1,9-dihydro-9-(2-fluoro-3-hydroxy-4-(hydroxymethyl)cyclopentyl)-6H-purin-6-one(110289-24-2)

Safety Data

• Hazardous Substances Data: 110289-24-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-amino-1,9-dihydro-9-(2-fluoro-3-hydroxy-4-(hydroxymethyl)cyclopentyl)-6H-purin-6-one is used as a precursor in the synthesis of guanine derivatives, which are essential building blocks for the development of antiviral agents. These guanine derivatives possess antiviral properties, making them valuable in the creation of virucides to combat viral infections.
Used in Chemical Research:
2-amino-1,9-dihydro-9-(2-fluoro-3-hydroxy-4-(hydroxymethyl)cyclopentyl)-6H-purin-6-one is also utilized in chemical research for studying the structure-activity relationships of purine-based molecules and their potential applications in medicinal chemistry. The unique cyclopentyl structure with fluorine and hydroxyl groups allows researchers to explore novel chemical modifications and investigate their effects on biological activity.

InChI:InChI=1/C11H14FN5O3/c12-6-5(1-4(2-18)8(6)19)17-3-14-7-9(17)15-11(13)16-10(7)20/h3-6,8,18-19H,1-2H2,(H3,13,15,16,20)/t4-,5?,6-,8-/m0/s1

Upstream product

• 110312-76-0 (+/-)-(1α,2β,3α,4α)-4-amino-3-fluoro-2-hydroxycyclopentanemethanol hydrochloride salt 
• 54112-42-4 trans-4-Hydroxy-2-cyclopenten-1-methanol 
• 110289-12-8 (1S,4S)-4-Trityloxymethyl-cyclopent-2-enol 
• 110289-09-3 (+/-)-(1α,2β,3α,4α)-4-<<2-amino-6-chloro-5-<(4-chlorophenyl)azo>-4-pyrimidinyl>amino>-3-fluoro-2-hydroxycyclopentanemethanol 
• 110289-11-7 (+/-)-(1α,2β,3α,4α)-4-<(2,5-diamino-6-chloro-4-pyrimidinyl)amino>-3-fluoro-2-hydroxycyclopentanemethanol 
• 110289-10-6 (+/-)-(1α,2β,3α,4α)-4-<(2-amino-6-chloro-4-pyrimidinyl)amino>-3-fluoro-2-hydroxycyclopentanemethanol 
• 110289-08-2 (1S,2S,3S,5S)-3-Amino-2-fluoro-5-hydroxymethyl-cyclopentanol 
• 110289-21-9 (+/-)-(1α,2β,3α,4α)-4-<(2-amino-6-chloro-9H-purin-9-yl)amino>-3-fluoro-2-hydroxycyclopentanemethanol 

Relevant articles and documents

Fluorocarbocyclic nucleosides: Synthesis and antiviral activity of 2'- and 6'-fluorocarbocyclic 2'-deoxy guanosines

A series of four isomeric 2'- and 6'-fluorocarbocyclic guanosine analogues have been prepared and evaluated as potential anti-herpes agents. The racemic 2'β-fluoro isomer 2-amino-1,9-dihydro-9-[(1α,2α,3β,4α)-2-fluoro-3-hydroxy-4- (hydroxymethyl)cyclopentyl]-6H-purin-6-one (11a, C-AFG) and its 2'α-fluoro epimer 11b plus the chiral 6'β-fluoro isomer 2-amino-1,9-dihydro-9-[[1S-(1α,2α,3α,4β)]-2-fluoro-4- hydroxy-3-(hydroxymethyl)cyclopentyl]-6H-purin-6-one (11c) and its 6'α-fluoro epimer 11d were prepared from their respective fluoro amino diol hydrochlorides (6a,d). For comparison, the furanosyl compound 9-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)guanine (17, AFG) was prepared by coupling 2-amino-6-chloropurine with 2-deoxy-2-fluoro-3,5-di-O- benzoyl-α-D-arabinofuranosyl bromide followed by base hydrolysis. The 6'α-fluoro derivative 11d exhibited comparable activity to that of acyclovir (ACV) against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) in vitro but was >30-fold more active than ACV against HSV-1 and HSV-2 in vivo in the mouse systemic model. The 2'β-fluoro derivative (11a, C-AFG) was extremely potent in vitro against HSV-1 and HSV-2 (ID50 0.006 and 0.005 μg/mL) and in vivo it was greater than 2 orders of magnitude more potent than ACV against HSV-1 and 70-fold more potent against HSV-2. The 2'α-fluoro 11b and 6'β-fluoro 11c isomers were much less active.