structure of 2',3',5'-Tri-O-benzoyl-4'-C-fluoroadenosine

2',3',5'-Tri-O-benzoyl-4'-C-fluoroadenosine

CAS No.: 1000203-40-6
M. Wt: 597.550
M. Fa: C31H24FN5O7
InChI Key: VRWGCWSOBIIKSR-GSBWNNRNSA-N

Names and Identifiers of 1000203-40-6

CAS Number

1000203-40-6

IUPAC Name

[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dibenzoyloxy-2-fluorooxolan-2-yl]methyl benzoate

InChI

InChI=1S/C31H24FN5O7/c32-31(16-41-28(38)19-10-4-1-5-11-19)24(43-30(40)21-14-8-3-9-15-21)23(42-29(39)20-12-6-2-7-13-20)27(44-31)37-18-36-22-25(33)34-17-35-26(22)37/h1-15,17-18,23-24,27H,16H2,(H2,33,34,35)/t23-,24+,27-,31-/m1/s1

InChIKey

VRWGCWSOBIIKSR-GSBWNNRNSA-N

Canonical SMILES

C1=CC=C(C=C1)C(=O)OCC2(C(C(C(O2)N3C=NC4=C(N=CN=C43)N)OC(=O)C5=CC=CC=C5)OC(=O)C6=CC=CC=C6)F

Isomeric SMILES

C1=CC=C(C=C1)C(=O)OC[C@@]2([C@H]([C@H]([C@@H](O2)N3C=NC4=C(N=CN=C43)N)OC(=O)C5=CC=CC=C5)OC(=O)C6=CC=CC=C6)F

Physical and chemical properties of 1000203-40-6

Boiling Point

781.4±70.0 °C at 760 mmHg

Density

1.5±0.1 g/cm3

Exact Mass

597.165955

Flash Point

426.4±35.7 °C

Index of Refraction

1.679

LogP

7.66

Molecular Formula

C31H24FN5O7

Molecular Weight

597.550

Vapour Pressure

0.0±2.7 mmHg at 25°C

Applications of 1000203-40-6

This compound has several applications in biochemical research and pharmaceutical development:

  • Nucleotide Analog Studies: It serves as a model compound for studying nucleotide metabolism and transport mechanisms.
  • Antiviral Research: Its modified structure may enhance antiviral activity, making it a candidate for developing new antiviral therapies.
  • Chemical Biology: Used in probing cellular processes involving nucleotides, such as signaling pathways and gene expression regulation.

Interaction Studies of 1000203-40-6

Interaction studies have shown that 2',3',5'-Tri-O-benzoyl-4'-C-fluoroadenosine can bind to various enzymes and receptors involved in nucleotide metabolism. Its unique structure allows it to interact selectively with certain kinases and transporters, leading to altered cellular responses compared to unmodified nucleosides. These interactions are crucial for understanding how modifications can affect biological activity and therapeutic potential.

Biological Activity of 1000203-40-6

2',3',5'-Tri-O-benzoyl-4'-C-fluoroadenosine exhibits notable biological activities, particularly in its interaction with nucleoside transporters and kinases. The fluorine atom enhances its affinity for certain biological targets, making it a useful tool in studying nucleotide metabolism and signaling pathways. It has been investigated for its potential antiviral properties, as modifications in nucleosides can often lead to increased efficacy against viral infections.