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30399 Fluka

Cytosine β-D-arabinofuranoside

≥99.0% (HPLC)

Synonym: (β-D-Arabinofuranosyl)cytosine, Ara-C, Arabinocytidine, Arabinosylcytosine, Cytarabine, Cytosine arabinoside

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Properties

assay   ≥99.0% (HPLC)
optical activity   [α]20/D +158±2°, c = 1% in H2O
solubility   H2O: soluble50 mg/mL, clear, colorless
Gene Information   human ... POLB(5423)
mouse ... Cda(72269)

Description

Biochem/physiol Actions

Ara-C incorporates into DNA and inhibits DNA replication by forming cleavage complexes with topoisomerase I resulting in DNA fragmentation; does not inhibit RNA synthesis. Anti-leukemia agent.

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Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
Precautionary statements 
WGK Germany 
3
RTECS 
HA5425000

Protocols & Articles

Peer-Reviewed Papers

References

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Structure-activity relationship and molecular mechanisms of ethyl 2-amino-6-(3,5-dimethoxyphenyl)-4-(2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate (CXL017) and its analogues. Sonia G Das et al J. Med. Chem. 54, 5937-48, (2011)

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Application of the dipeptidyl peptidase IV (DPPIV/CD26) based prodrug approach to different amine-containing drugs. Alberto Diez-Torrubia et al J. Med. Chem. 53, 559-72, (2010)

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Novel effects of glycyrrhetinic acid on the central nervous system tumorigenic progenitor cells: induction of actin disruption and tumor cell-selective toxicity. Hideaki Yamaguchi et al Eur. J. Med. Chem. 45, 2943-8, (2010)

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Antitumor studies. Part 1: design, synthesis, antitumor activity, and AutoDock study of 2-deoxo-2-phenyl-5-deazaflavins and 2-deoxo-2-phenylflavin-5-oxides as a new class of antitumor agents. Hamed I Ali et al Bioorg. Med. Chem. 15, 242-56, (2007)

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Spectrophotometric determination of drugs with iodine. Karuna T, et al. J. Sci. Ind. Res. 65(10), 808, (2006)

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FDA-approved drug labeling for the study of drug-induced liver injury. Minjun Chen et al Drug Discov. Today 16, 697-703, (2011)

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Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors. Lourdes Santana et al J. Med. Chem. 51, 6740-51, (2008)

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Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species. Denis Fourches et al Chem. Res. Toxicol. 23, 171-83, (2010)

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Novel selective human mitochondrial kinase inhibitors: design, synthesis and enzymatic activity. Nunzia Ciliberti et al Bioorg. Med. Chem. 15, 3065-81, (2007)

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In vitro optimization of non-small cell lung cancer activity with troxacitabine, L-1,3-dioxolane-cytidine, prodrugs. Marco Radi et al J. Med. Chem. 50, 2249-53, (2007)

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In silico prediction of volume of distribution in human using linear and nonlinear models on a 669 compound data set. Giuliano Berellini et al J. Med. Chem. 52, 4488-95, (2009)

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The design, synthesis, and antiviral activity of 4'-azidocytidine analogues against hepatitis C virus replication: the discovery of 4'-azidoarabinocytidine. David B Smith et al J. Med. Chem. 52, 219-23, (2009)

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Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species. Francisco J Prado-Prado et al Bioorg. Med. Chem. 18, 2225-31, (2010)

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Synthesis and in vitro cytostatic activity of new beta-D-arabino furan[1',2':4,5]oxazolo- and arabino-pyrimidinone derivatives. Jean-Jacques Bosc et al Eur. J. Med. Chem. 45, 831-9, (2010)

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Probing the anticancer activity of nucleoside analogues: a QSAR model approach using an internally consistent training set. Aliuska Morales Helguera et al J. Med. Chem. 50, 1537-45, (2007)

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Synthesis and characterization of a novel liver-targeted prodrug of cytosine-1-beta-D-arabinofuranoside monophosphate for the treatment of hepatocellular carcinoma. Serge H Boyer et al J. Med. Chem. 49, 7711-20, (2006)

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Structure-activity relationship and molecular mechanisms of ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)-6-phenyl-4h-chromene-3-carboxylate (sha 14-1) and its analogues. Sonia G Das et al J. Med. Chem. 52, 5937-49, (2009)

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Novel N-(3-carboxyl-9-benzyl-beta-carboline-1-yl)ethylamino acids: synthesis, anti-tumor evaluation, intercalating determination, 3D QSAR analysis and docking investigation. Jianhui Wu et al Eur. J. Med. Chem. 44, 4153-61, (2009)

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Synthesis of potent antitumor and antiviral benzofuran derivatives. Shadia A Galal et al Bioorg. Med. Chem. Lett. 19, 2420-8, (2009)

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Discovery of a new template for anticancer agents: 2'-deoxy-2'-fluoro-4'-selenoarabinofuranosyl-cytosine (2'-F-4'-seleno-ara-C). Lak Shin Jeong et al J. Med. Chem. 52, 5303-6, (2009)

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Synthesis of 5-isoxazol-5-yl-2'-deoxyuridines exhibiting antiviral activity against HSV and several RNA viruses. Yoon-Suk Lee et al Bioorg. Med. Chem. Lett. 19, 1126-8, (2009)

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Novel benzimidazole-pyrimidine conjugates as potent antitumor agents. Heba T Abdel-Mohsen et al Eur. J. Med. Chem. 45, 2336-44, (2010)

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Synthesis, X-ray crystal structure study and antitumoral evaluations of 5,6-disubstituted pyrimidine derivatives. Tatjana Gazivoda Kraljevi? et al Bioorg. Med. Chem. 18, 2704-12, (2010)

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Antitumor studies. Part 4: Design, synthesis, antitumor activity, and molecular docking study of novel 2-substituted 2-deoxoflavin-5-oxides, 2-deoxoalloxazine-5-oxides, and their 5-deaza analogs. Hamed I Ali et al Bioorg. Med. Chem. 16, 922-40, (2008)

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Assessment of in vitro and in vivo activities in the National Cancer Institute's anticancer screen with respect to chemical structure, target specificity, and mechanism of action. Ruili Huang et al J. Med. Chem. 49, 1964-79, (2006)

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New uracil dimers showing erythroid differentiation inducing activities. Alessandro Accetta et al J. Med. Chem. 52, 87-94, (2009)

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A class of Trp-Trp-AA-OBzl: Synthesis, in vitro anti-proliferation/in vivo anti-tumor evaluation, intercalation-mechanism investigation and 3D QSAR analysis. Xiaoyi Zhang et al Eur. J. Med. Chem. 46, 3410-9, (2011)

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Antitumor studies. part 3: design, synthesis, antitumor activity, and molecular docking study of novel 2-methylthio-, 2-amino-, and 2-(N-substituted amino)-10-alkyl-2-deoxo-5-deazaflavins. Hamed I Ali et al Bioorg. Med. Chem. 15, 6336-52, (2007)

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A class of novel carboline intercalators: Their synthesis, in vitro anti-proliferation, in vivo anti-tumor action, and 3D QSAR analysis. Jianhui Wu et al Bioorg. Med. Chem. 18, 6220-9, (2010)

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Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models. Naomi L Kruhlak et al Toxicol. Mech. Methods 18, 217-27, (2008)

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Synthesis, biological active molecular design, and molecular docking study of novel deazaflavin-cholestane hybrid compounds. Ajaya R Shrestha et al Bioorg. Med. Chem. 16, 8685-96, (2008)

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Antitumor studies -- part 2: structure-activity relationship study for flavin analogs including investigations on their in vitro antitumor assay and docking simulation into protein tyrosine kinase. Hamed I Ali et al Eur. J. Med. Chem. 43, 1376-89, (2008)

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Synthesis of 3'-azido-3'-deoxythymidine (AZT)--Cinchona alkaloid conjugates via click chemistry: Toward novel fluorescent markers and cytostatic agents. Dagmara Baraniak et al Bioorg. Med. Chem. Lett. 21, 723-6, (2011)

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QSPR modeling of octanol/water partition coefficient of antineoplastic agents by balance of correlations. Andrey A Toropov et al Eur. J. Med. Chem. 45, 1639-47, (2010)

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Synthesis of glycose carbamides and evaluation of the induction of erythroid differentiation of human erythroleukemic K562 cells. Martina Landi et al Eur. J. Med. Chem. 44, 745-54, (2009)

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Antitumor studies. Part 5: Synthesis, antitumor activity, and molecular docking study of 5-(monosubstituted amino)-2-deoxo-2-phenyl-5-deazaflavins. Ajaya R Shrestha et al Bioorg. Med. Chem. 16, 9161-70, (2008)

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Synthesis and anticancer activity of 5'-chloromethylphosphonates of 3'-azido-3'-deoxythymidine (AZT). Lech Celewicz et al Bioorg. Med. Chem. 19, 6375-82, (2011)

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Indirubin derivatives as potent FLT3 inhibitors with anti-proliferative activity of acute myeloid leukemic cells. Soo Jeong Choi et al Bioorg. Med. Chem. Lett. 20, 2033-7, (2010)

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Synthesis, DNA intercalation and 3D QSAR analysis of cis-2,4,5-trisubstituted-1,3-dithiolanes as a novel class of antitumor agents. Fei Huang et al Bioorg. Med. Chem. 17, 6085-95, (2009)

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A class of novel N-isoquinoline-3-carbonyl-L-amino acid benzylesters: synthesis, anti-tumor evaluation and 3D QSAR analysis. Meiqing Zheng et al Eur. J. Med. Chem. 46, 1672-81, (2011)

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Synthesis of radiolabeled cytarabine conjugates. Pallavi Lagisetty et al Bioorg. Med. Chem. Lett. 19, 4764-7, (2009)

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Merck 14,2784

Beil. 25,IV,3669

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