A0928
Aristeromycin
~95%
Synonym(s):
9-(2,3-Dihydroxy-4-[hydroxymethyl]cyclopentyl)adenine
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About This Item
Empirical Formula (Hill Notation):
C11H15N5O3
CAS Number:
Molecular Weight:
265.27
MDL number:
UNSPSC Code:
51101500
PubChem Substance ID:
Assay
~95%
antibiotic activity spectrum
viruses
storage temp.
2-8°C
SMILES string
Nc1ncnc2n(cnc12)[C@@H]3C[C@H](CO)[C@@H](O)[C@H]3O
InChI
1S/C11H15N5O3/c12-10-7-11(14-3-13-10)16(4-15-7)6-1-5(2-17)8(18)9(6)19/h3-6,8-9,17-19H,1-2H2,(H2,12,13,14)/t5-,6-,8-,9+/m1/s1
InChI key
UGRNVLGKAGREKS-GCXDCGAKSA-N
Gene Information
human ... ADORA2B(136)
rat ... Adora1(29290), Adora2a(25369), Adora3(25370)
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
涉药品监管产品
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Padraick J Dornbush et al.
Bioorganic & medicinal chemistry letters, 20(24), 7466-7468 (2010-11-04)
Trypanosoma brucei and Trichomonas vaginalis are both parasitic protozoans that are known to share many similar biochemical pathways. Aristeromycin, as well as 5'-iodovinyl and 5'-oxime analogues of adenosine, are potent inhibitors of AdoHcy hydrolase in T. brucei, an enzyme that
S F Wnuk et al.
Nucleosides & nucleotides, 17(1-3), 99-113 (1998-08-26)
Moffatt oxidation of 2',3'-O-isopropylidenearisteromycin (1a) and treatment of the 5'-carboxaldehyde with [(p-tolylsulfonyl)methylene]triphenylphosphorane gave the homologated vinylsulfone 2. Treatment of 2 with tributylstannane/AIBN gave the (E/Z)-vinylstannanes which were converted into the E and Z fluoro- and iodovinyl analogs. Chain extension via
Stereoselective synthesis of a novel carbocyclic nucleoside.
M K Gurjar et al.
The Journal of organic chemistry, 66(22), 7552-7554 (2001-10-30)
Atanu Roy et al.
Bioorganic & medicinal chemistry, 14(14), 4980-4986 (2006-04-04)
The promising antiviral properties of 3'-fluoro-3'-deoxyadenosine and 4',4'-difluoro-4'-deoxy-5'-noraristeromycin prompted the synthesis of the corresponding 3'-fluoro derivatives of 5'-noraristeromycin. These target compounds, which were prepared from the same readily accessible cyclopentenol, were found to be inactive when subjected to 31 viral
Meral Tuncbilek et al.
Bioorganic & medicinal chemistry, 11(15), 3331-3334 (2003-07-03)
9-deaza-5'-noraristeromycin (2) has been prepared in 10 steps from the readily available (+)-(1R,4S)-4-t-butyldimethylsilyloxycyclopent-2-en-1-yl acetate. Compound 2 was evaluated against a large number of viruses. No activity was found nor did 2 display cyctotoxicity towards the viral host cells.
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