6-Chloroguanineriboside

Names

[ CAS No. ]:
2004-07-1

[ Name ]:
6-Chloroguanineriboside

[Synonym ]:
(−)-2-Amino-6-chloropurine riboside 6-Chloroguanine riboside
6-Chloroguanineriboside
2-Amino-6-chloro-9-(β-D-ribofuranosyl)purine
6-Chloro-9-(β-D-ribofuranosyl)-9H-purin-2-amine
EINECS 217-905-3
(−)-2-Amino-6-chloropurine riboside
6-CHLOROGUANOSINE
2-Amino-6-chloropurine Riboside
6-Chloroguanine nucleoside
6-CHLOROADENOSINE
6-Chloroguanosine2
MFCD00005735
2-Amino-6-chloropurine-9--D-riboside
9H-Purin-2-amine, 6-chloro-9-β-D-ribofuranosyl-
6-Chloroguanine riboside
2-amino-6-chloro purineriboside

Biological Activity

[Description]:

6-Chloroguanineriboside (6-Chloroguanosine) is a purine nucleoside analogue. Purine nucleoside analogs have broad antitumor activity targeting indolent lymphoid malignancies. Anticancer mechanisms in this process rely on inhibition of DNA synthesis, induction of apoptosis, etc[1].

[Related Catalog]:

Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog

Research Areas >> Others

[References]

[1]. Robak T, Robak P. Purine nucleoside analogs in the treatment of rarer chronic lymphoid leukemias. Curr Pharm Des. 2012;18(23):3373-88.

Chemical & Physical Properties

[ Density]:
2.2±0.1 g/cm3

[ Boiling Point ]:
729.9±70.0 °C at 760 mmHg

[ Melting Point ]:
165-167 °C (dec.)(lit.)

[ Molecular Formula ]:
C₁₀H₁₂ClN₅O₄

[ Molecular Weight ]:
301.69

[ Flash Point ]:
395.2±35.7 °C

[ Exact Mass ]:
301.057770

[ PSA ]:
139.54000

[ LogP ]:
-0.59

[ Vapour Pressure ]:
0.0±2.5 mmHg at 25°C

[ Index of Refraction ]:
1.912

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Preparative electrochemical reduction of 2-amino-6-chloropurine and synthesis of 6-deoxyacyclovir, a fluorescent substrate of xanthine oxidase and a prodrug of acyclovir.

Acta Chem. Scand. B 41 , 701-707, (1987)

D.c. polarography of 2-amino-6-chloropurine in aqueous medium over a broad pH range revealed two diffusion waves, the first of which corresponds to reduction of the C(6)-Cl bond, leading to formation ...

Synthesis of a mutagenic nucleoside, 2'-deoxy-2-(p-nitrophenyl)-adenosine.

Nucleic Acids Symp. Ser. 17 , 141-143, (1986)

The reaction of 2-amino-6-chloropurine riboside with i-amyl nitrite in benzene in the presence of Cu2O, followed by treatment with NH3/MeOH gave 2-phenyladenosine (1). The crude sample of 1 was found ...

Synthesis of 6-arylthio analogs of 2',3'-dideoxy-3'-fluoroguanosine and their effect against hepatitis B virus replication.

Nucleosides Nucleotides Nucleic Acids 25 , 655-665, (2006)

A key compound, 2-amino-6-chlor-9-(2,3-dideoxy-3-fluoro-beta-D-erythro-pentofuranosyl)puine, was prepared from 2-amino-6-chloropurine riboside in 5 steps, then subjected to the nucleophilic displaceme...