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3416-05-5,MFCD00010570
Catalog No.:AA00I6OA

3416-05-5 | 2',3'-Dideoxythymidine

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Purity
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25mg
≥98%
in stock  
$53.00   $37.00
- +
50mg
≥98%
in stock  
$93.00   $65.00
- +
100mg
≥98%
in stock  
$165.00   $115.00
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1g
97%
in stock  
$199.00   $139.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00I6OA
Chemical Name:
2',3'-Dideoxythymidine
CAS Number:
3416-05-5
Molecular Formula:
C10H14N2O4
Molecular Weight:
226.2292
MDL Number:
MFCD00010570
SMILES:
Cc1cn([C@H]2CC[C@H](O2)CO)c(=O)[nH]c1=O
Properties
Computed Properties
 
Complexity:
353  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
16  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
2  
XLogP3:
-1.7  

Downstream Synthesis Route
66085-16-3    3416-05-5   
6-isopropoxy-9-<(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furyl>-9H-purine 

[1]Burns;St.Clair;Frick;Spector;Averett;English;Holmes;Krenitsky;Koszalka[JournalofMedicinalChemistry,1993,vol.36,#3,p.378-384]

3416-05-5    17861-06-2   
6-ethoxy-9-<(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furyl>-9H-purine 

[1]Burns;St.Clair;Frick;Spector;Averett;English;Holmes;Krenitsky;Koszalka[JournalofMedicinalChemistry,1993,vol.36,#3,p.378-384]

3416-05-5    5454-70-6   
6-butoxy-9-<(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furyl>-9H-purine 

[1]Burns;St.Clair;Frick;Spector;Averett;English;Holmes;Krenitsky;Koszalka[JournalofMedicinalChemistry,1993,vol.36,#3,p.378-384]

3416-05-5    5417-86-7   
6-propoxy-9-<(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furyl>-9H-purine 

[1]Burns;St.Clair;Frick;Spector;Averett;English;Holmes;Krenitsky;Koszalka[JournalofMedicinalChemistry,1993,vol.36,#3,p.378-384]

3416-05-5    146331-47-7   
6-(allyloxy)-9-<(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furyl>-9H-purine 

[1]Burns;St.Clair;Frick;Spector;Averett;English;Holmes;Krenitsky;Koszalka[JournalofMedicinalChemistry,1993,vol.36,#3,p.378-384]

Literature

Title: Synthesis of C3' modified nucleosides for selective generation of the C3'-deoxy-3'-thymidinyl radical: a proposed intermediate in LEE induced DNA damage.

Journal: The Journal of organic chemistry 20120420

Title: Synthesis, modeling and evaluation of 3'-(1-aryl-1H-tetrazol-5-ylamino)-substituted 3'-deoxythymidine derivatives as potent and selective human mitochondrial thymidine kinase inhibitors.

Journal: Organic & biomolecular chemistry 20110207

Title: Computational design of orthogonal nucleoside kinases.

Journal: Chemical communications (Cambridge, England) 20101214

Title: Preparation of 4'-benzenesulfonyl-3'-deoxythymidine and its reaction with organoaluminum and organosilicon reagents.

Journal: Carbohydrate research 20101210

Title: Synthesis of fluorescent nucleoside analogs as probes for 2'-deoxyribonucleoside kinases.

Journal: Bioorganic & medicinal chemistry letters 20100201

Title: Bisphosphonate inhibitors of ATP-mediated HIV-1 reverse transcriptase catalyzed excision of chain-terminating 3'-azido, 3'-deoxythymidine: a QSAR investigation.

Journal: Bioorganic & medicinal chemistry 20081001

Title: Kinetic parameters and recognition of thymidine analogues with varying functional groups by thymidine phosphorylase.

Journal: Bioorganic & medicinal chemistry 20080401

Title: Axon-bearing and axon-less horizontal cell subtypes are generated consecutively during chick retinal development from progenitors that are sensitive to follistatin.

Journal: BMC developmental biology 20080101

Title: How many conformers determine the thymidine low-temperature matrix infrared spectrum? DFT and MP2 quantum chemical study.

Journal: The journal of physical chemistry. B 20070816

Title: Synthesis, anti-HIV activity, and resistance profile of thymidine phosphonomethoxy nucleosides and their bis-isopropyloxymethylcarbonyl (bisPOC) prodrugs.

Journal: Bioorganic & medicinal chemistry 20070815

Title: Induction of thymidine phosphorylase expression by AZT contributes to enhancement of 5'-DFUR cytotoxicity.

Journal: Cancer letters 20061208

Title: Antiretroviral nucleosides, deoxynucleotide carrier and mitochondrial DNA: evidence supporting the DNA pol gamma hypothesis.

Journal: AIDS (London, England) 20060321

Title: Synthesis and in vitro anti-mycobacterial activity of 5-substituted pyrimidine nucleosides.

Journal: Bioorganic & medicinal chemistry 20051215

Title: Transgenic expression of the deoxynucleotide carrier causes mitochondrial damage that is enhanced by NRTIs for AIDS.

Journal: Laboratory investigation; a journal of technical methods and pathology 20050801

Title: In vitro activity of structurally diverse nucleoside analogs against human immunodeficiency virus type 1 with the K65R mutation in reverse transcriptase.

Journal: Antimicrobial agents and chemotherapy 20050301

Title: Endophilins interact with Moloney murine leukemia virus Gag and modulate virion production.

Journal: Journal of biology 20040101

Title: Bis-ketol nucleoside triesters as prodrugs of the antiviral nucleoside triphosphate analogues of 3'-deoxythymidine and 3'-deoxy-2',3'-didehydrothymidine.

Journal: Nucleosides, nucleotides & nucleic acids 20040101

Title: Effect of transport inhibitors and additional anti-HIV drugs on the movement of lamivudine (3TC) across the guinea pig brain barriers.

Journal: The Journal of pharmacology and experimental therapeutics 20030901

Title: An age-related increase in resistance to DNA damage-induced apoptotic cell death is associated with development of DNA repair mechanisms.

Journal: Journal of neurochemistry 20030301

Title: Mechanisms by which 2',3'-dideoxyinosine (ddI) crosses the guinea-pig CNS barriers; relevance to HIV therapy.

Journal: Journal of neurochemistry 20030201

Title: The distribution of the anti-HIV drug, 2'3'-dideoxycytidine (ddC), across the blood-brain and blood-cerebrospinal fluid barriers and the influence of organic anion transport inhibitors.

Journal: Journal of neurochemistry 20020201

Title: Efficacy of 3'-azido 3'deoxythymidine (AZT) in preventing HTLV-1 transmission to human cord blood mononuclear cells.

Journal: Virus research 20011030

Title: Stimulatory effect of zinc on deoxyribonucleic acid synthesis in bone growth of newborn rats: enhancement with zinc and insulin-like growth factor-I.

Journal: Calcified tissue international 20010901

Title: Targeting of 3'-azido 3'-deoxythymidine (AZT)-loaded poly(isohexylcyanoacrylate) nanospheres to the gastrointestinal mucosa and associated lymphoid tissues.

Journal: Pharmaceutical research 20010401

Title: Activities of masked 2',3'-dideoxynucleoside monophosphate derivatives against human immunodeficiency virus in resting macrophages.

Journal: Antimicrobial agents and chemotherapy 20000101

Title: Aryl phosphate derivatives of 3'-deoxythymidine are not potent anti-human immunodeficiency virus agents.

Journal: Antiviral chemistry & chemotherapy 19980901

Title: Inhibition of sandfly fever Sicilian virus (Phlebovirus) replication in vitro by antiviral compounds.

Journal: Research in virology 19970101

Title: 3',3'-Difluoro-3'-deoxythymidine: comparison of anti-HIV activity to 3'-fluoro-3'-deoxythymidine.

Journal: Journal of medicinal chemistry 19920904

Title: Greatly enhanced inhibition of human immunodeficiency virus type 1 replication in CEM and HT4-6C cells by 3'-deoxythymidine diphosphate dimyristoylglycerol, a lipid prodrug of 3'-deoxythymidine.

Journal: Antimicrobial agents and chemotherapy 19920901

Title: Use of a standardized cell culture assay to assess activities of nucleoside analogs against hepatitis B virus replication.

Journal: Antiviral research 19920701

Title: Synergistic inhibition of human immunodeficiency virus type 1 replication in vitro by two-drug and three-drug combinations of 3'-azido-3'-deoxythymidine, phosphonoformate, and 2',3'-dideoxythymidine.

Journal: Antimicrobial agents and chemotherapy 19911001

Title: Synthesis and antiretroviral activity of phospholipid analogs of azidothymidine and other antiviral nucleosides.

Journal: The Journal of biological chemistry 19900415

Title: Synthesis and antiviral activity of several 2,5'-anhydro analogues of 3'-azido-3'-deoxythymidine, 3'-azido-2',3'-dideoxyuridine, 3'-azido-2',3'-dideoxy-5-halouridines, and 3'-deoxythymidine against human immunodeficiency virus and Rauscher-murine leukemia virus.

Journal: Journal of medicinal chemistry 19890801

Title: Replication of human immunodeficiency virus in monocytes. Granulocyte/macrophage colony-stimulating factor (GM-CSF) potentiates viral production yet enhances the antiviral effect mediated by 3'-azido-2'3'-dideoxythymidine (AZT) and other dideoxynucleoside congeners of thymidine.

Journal: The Journal of experimental medicine 19890301

Title: Structure-activity relationships of pyrimidine nucleosides as antiviral agents for human immunodeficiency virus type 1 in peripheral blood mononuclear cells.

Journal: Journal of medicinal chemistry 19890301

Title: Comparative activity of 2',3'-saturated and unsaturated pyrimidine and purine nucleosides against human immunodeficiency virus type 1 in peripheral blood mononuclear cells.

Journal: Biochemical pharmacology 19881001

Title: Adenallene and cytallene: acyclic-nucleoside analogues that inhibit replication and cytopathic effect of human immunodeficiency virus in vitro.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19880801

Title: Anti-retrovirus activity of 3'-fluoro- and 3'-azido-substituted pyrimidine 2',3'-dideoxynucleoside analogues.

Journal: Biochemical pharmacology 19880715

Title: Dextran sulfate suppression of viruses in the HIV family: inhibition of virion binding to CD4+ cells.

Journal: Science (New York, N.Y.) 19880429

Title: The in vitro and in vivo anti-retrovirus activity, and intracellular metabolism of 3'-azido-2',3'-dideoxythymidine and 2',3'-dideoxycytidine are highly dependent on the cell species.

Journal: Biochemical pharmacology 19880301

Title: Dideoxynucleosides are less inhibitory in vitro against human immunodeficiency virus type 2 (HIV-2) than against HIV-1.

Journal: Antimicrobial agents and chemotherapy 19871201

Title: Potent and selective in vitro activity of 3'-deoxythymidin-2'-ene (3'-deoxy-2',3'-didehydrothymidine) against human immunodeficiency virus.

Journal: Biochemical pharmacology 19870901

Title: 3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.

Journal: Journal of medicinal chemistry 19870801

Title: The anti-HTLV-III (anti-HIV) and cytotoxic activity of 2',3'-didehydro-2',3'-dideoxyribonucleosides: a comparison with their parental 2',3'-dideoxyribonucleosides.

Journal: Molecular pharmacology 19870701

Title: Inhibitory effect of 2',3'-didehydro-2',3'-dideoxynucleosides on infectivity, cytopathic effects, and replication of human immunodeficiency virus.

Journal: Antimicrobial agents and chemotherapy 19870601

Title: Potential anti-AIDS drugs. 2',3'-Dideoxycytidine analogues.

Journal: Journal of medicinal chemistry 19870501

Title: Synthesis and antiviral activity of various 3'-azido, 3'-amino, 2',3'-unsaturated, and 2',3'-dideoxy analogues of pyrimidine deoxyribonucleosides against retroviruses.

Journal: Journal of medicinal chemistry 19870201

Title: Both 2',3'-dideoxythymidine and its 2',3'-unsaturated derivative (2',3'-dideoxythymidinene) are potent and selective inhibitors of human immunodeficiency virus replication in vitro.

Journal: Biochemical and biophysical research communications 19870115

Title: Inhibition of the in vitro infectivity and cytopathic effect of human T-lymphotrophic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV) by 2',3'-dideoxynucleosides.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19860301

Title: In vivo antiherpetic activity of deoxythymidine.

Journal: Biochemical pharmacology 19740315

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Tags:3416-05-5 Molecular Formula|3416-05-5 MDL|3416-05-5 SMILES|3416-05-5 2',3'-Dideoxythymidine |Heterocyclic_Building_Blocks