01832
Adenine 9-β-D-arabinofuranoside
≥99.0% (HPLC)
Synonym(s):
9-β-D-Arabinofuranosyladenine, Ara-A, Vidarabine
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About This Item
Empirical Formula (Hill Notation):
C10H13N5O4
CAS Number:
Molecular Weight:
267.24
EC Number:
226-893-9
UNSPSC Code:
41106305
MDL number:
Beilstein/REAXYS Number:
624881
InChI
1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7+,10-/m1/s1
InChI key
OIRDTQYFTABQOQ-UHTZMRCNSA-N
SMILES string
Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3O
assay
≥99.0% (HPLC)
antibiotic activity spectrum
viruses
mode of action
DNA synthesis | interferes, enzyme | inhibits
General description
Chemical structure: nucleoside
Biochem/physiol Actions
Cell-permeable adenylate cyclase inhibitor; in detergent-dispersed rat brain preparation, IC50 = 30 μM. Clinically significant antiviral agent, especially against herpes simplex (HSV), by inhibition of DNA polymerase.
Cell-permeable adenylyl cyclase inhibitor. IC50 = 30 μM in detergent-dispersed rat brain preparation.
Regulatory Information
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Larryn W Peterson et al.
Bioorganic & medicinal chemistry letters, 21(13), 4045-4049 (2011-06-07)
We report the synthesis and biological evaluation of Ala-(Val-)l-Ser-CO(2)R prodrugs of 1, where a dipeptide promoiety is conjugated to the P(OH)(2) group of cidofovir (1) via esterification by the Ser side chain hydroxyl group and an ethyl group (4 and
Wei Shen et al.
Bioorganic & medicinal chemistry letters, 19(3), 792-796 (2008-12-23)
5'-O-D- and L-amino acid derivatives and 5'-O-(D- and L-amino acid methyl ester phosphoramidate) derivatives of vidarabine (ara-A) were synthesized as vidarabine prodrugs. Some compounds were equi- or more potent in vitro than vidarabine against two pox viruses and their uptake
Tadashi Terasaka et al.
Journal of medicinal chemistry, 48(15), 4750-4753 (2005-07-22)
From metabolic considerations and prediction of an inhibitor-induced conformational change, novel adenosine deaminase (ADA) inhibitors with improved activities and oral bioavailability have been developed on the basis of our originally designed non-nucleoside ADA inhibitors. They demonstrated in vivo efficacy in
Inhibition of B virus (Macacine herpesvirus 1) by conventional and experimental antiviral compounds.
P W Krug et al.
Antimicrobial agents and chemotherapy, 54(1), 452-459 (2009-10-28)
B virus infection of humans results in high morbidity and mortality in as many as 80% of identified cases. The main objective of this study was to conduct a comparative analysis of conventional and experimental antiviral drug susceptibilities of B
Paul B Yu et al.
Nature chemical biology, 4(1), 33-41 (2007-11-21)
Bone morphogenetic protein (BMP) signals coordinate developmental patterning and have essential physiological roles in mature organisms. Here we describe the first known small-molecule inhibitor of BMP signaling-dorsomorphin, which we identified in a screen for compounds that perturb dorsoventral axis formation
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