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4097-22-7,MFCD00010534
Catalog No.:AA00I7Y4

4097-22-7 | 2',3'-Dideoxyadenosine

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5mg
98%
in stock  
$42.00   $29.00
- +
100mg
95%
in stock  
$53.00   $37.00
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250mg
98%
in stock  
$114.00   $80.00
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1g
98%
in stock  
$309.00   $217.00
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5g
98%
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$1,499.00   $1,049.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00I7Y4
Chemical Name:
2',3'-Dideoxyadenosine
CAS Number:
4097-22-7
Molecular Formula:
C10H13N5O2
Molecular Weight:
235.2425
MDL Number:
MFCD00010534
SMILES:
OC[C@@H]1CC[C@@H](O1)n1cnc2c1ncnc2N
Properties
Computed Properties
 
Complexity:
279  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
17  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
2  
XLogP3:
-0.2  

Downstream Synthesis Route

[1]Robins,MorrisJ.;Hansske,Fritz;Low,NicholasH.;Park,JaIn[TetrahedronLetters,1984,vol.25,#4,p.367-370]

[2]Robins,MorrisJ.;Wilson,John,S.;Madej,Danuta;Low,NicholasH.;Hansske,Fritz;Wnuk,StanislawF.[JournalofOrganicChemistry,1995,vol.60,#24,p.7902-7908]

[3]Chu;Bhadti;Doboszewski;Gu;Kosugi;Pullaiah;VanRoey[JournalofOrganicChemistry,1989,vol.54,#9,p.2217-2225]

[4]Mansuri;StarrettJr.;Wos;Tortolani;Brodfuehrer;Howell;Martin[JournalofOrganicChemistry,1989,vol.54,#20,p.4780-4785]

[1]TetrahedronLetters,1988,vol.29,p.1239-1242

[2]TetrahedronLetters,1988,vol.29,p.1239-1242

[1]Kim;Misco[TetrahedronLetters,1992,vol.33,#39,p.5733-5736]

9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>adenine 
  4097-22-7 

[1]Sung,EunKim;Su,YeonKim;Kim,Sunghoon;Kang,Taehee;Lee,Jeewoo[BioorganicandMedicinalChemistryLetters,2005,vol.15,#14,p.3389-3393]

[2]Beach,J.Warren;Kim,HeaO.;Jeong,LakS.;Nampalli,Satyanarayana;Islam,Qamrul;etal.[JournalofOrganicChemistry,1992,vol.57,#14,p.3887-3894]

[1]Zeidler,Joanna;Golankiewicz,Bozenna[NucleosidesandNucleotides,1996,vol.15,#5,p.1077-1095]

[2]VanAerschot;Herdewijn;Balzarini;Pauwels;DeClercq[Journalofmedicinalchemistry,1989,vol.32,#8,p.1743-1749]

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Title: Acute cardiotoxicity of nucleoside analogs FddA and FddI in rats.

Journal: Fundamental and applied toxicology : official journal of the Society of Toxicology 19930401

Title: Potential prodrug derivatives of 2',3'-didehydro-2',3'-dideoxynucleosides. Preparations and antiviral activities.

Journal: Journal of medicinal chemistry 19920724

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

Journal: Antiviral research 19920701

Title: Synthesis and anti-HIV activity of isonucleosides.

Journal: Journal of medicinal chemistry 19920626

Title: Substrate specificity of human deoxycytidine kinase toward antiviral 2',3'-dideoxynucleoside analogs.

Journal: Biochemical pharmacology 19920122

Title: Potential anti-AIDS drugs. Lipophilic, adenosine deaminase-activated prodrugs.

Journal: Journal of medicinal chemistry 19910501

Title: Synthesis and anti-HIV activity of 2-, 3-, and 4-substituted analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT).

Journal: Journal of medicinal chemistry 19910401

Title: Inhibitory effects of selected antiviral compounds on human hepatitis B virus DNA synthesis.

Journal: Antimicrobial agents and chemotherapy 19910201

Title: A new class of HIV-1-specific 6-substituted acyclouridine derivatives: synthesis and anti-HIV-1 activity of 5- or 6-substituted analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT).

Journal: Journal of medicinal chemistry 19910101

Title: Lipophilic halogenated congeners of 2',3'-dideoxypurine nucleosides active against human immunodeficiency virus in vitro.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19901201

Title: Comparative activities of several nucleoside analogs against duck hepatitis B virus in vitro.

Journal: Antimicrobial agents and chemotherapy 19900701

Title: Synthesis and structure-activity relationships of 6-substituted 2',3'-dideoxypurine nucleosides as potential anti-human immunodeficiency virus agents.

Journal: Journal of medicinal chemistry 19900601

Title: Activities of 3'-azido-3'-deoxythymidine nucleotide dimers in primary lymphocytes infected with human immunodeficiency virus type 1.

Journal: Antimicrobial agents and chemotherapy 19900601

Title: Cyclobut-A and cyclobut-G: broad-spectrum antiviral agents with potential utility for the therapy of AIDS.

Journal: Journal of medicinal chemistry 19900501

Title: Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV.

Journal: Journal of medicinal chemistry 19900301

Title: Muramyl dipeptide inhibits replication of human immunodeficiency virus in vitro.

Journal: AIDS research and human retroviruses 19900301

Title: Cyclobut-A and cyclobut-G, carbocyclic oxetanocin analogs that inhibit the replication of human immunodeficiency virus in T cells and monocytes and macrophages in vitro.

Journal: Antimicrobial agents and chemotherapy 19900201

Title: Exacerbation of human immunodeficiency virus infection in promonocytic cells by bacterial immunomodulators.

Journal: Journal of acquired immune deficiency syndromes 19900101

Title: Potentiating effect of ribavirin on the in vitro and in vivo antiretrovirus activities of 2',3'-dideoxyinosine and 2',3'-dideoxy-2,6-diaminopurine riboside.

Journal: Journal of acquired immune deficiency syndromes 19900101

Title: Synthesis and anti-HIV activity of carbocyclic 2',3'-didehydro-2',3'-dideoxy 2,6-disubstituted purine nucleosides.

Journal: Journal of medicinal chemistry 19900101

Title: A novel lead for specific anti-HIV-1 agents: 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine.

Journal: Journal of medicinal chemistry 19891201

Title: 3'-Fluoro-2',3'-dideoxy-5-chlorouridine: most selective anti-HIV-1 agent among a series of new 2'- and 3'-fluorinated 2',3'-dideoxynucleoside analogues.

Journal: Journal of medicinal chemistry 19890801

Title: Nucleic acid related compounds. 57. Synthesis, x-ray crystal structure, lipophilic partition properties, and antiretroviral activities of anomeric 3'-azido-2',3'-dideoxy-2,6-diaminopurine ribosides.

Journal: Journal of medicinal chemistry 19890801

Title: Synthesis of the 2-chloro analogues of 3'-deoxyadenosine, 2',3'-dideoxyadenosine, and 2',3'-didehydro-2',3'-dideoxyadenosine as potential antiviral agents.

Journal: Journal of medicinal chemistry 19890501

Title: Inhibition of infectivity of human immunodeficiency virus by a novel nucleoside, oxetanocin, and related compounds.

Journal: Antimicrobial agents and chemotherapy 19890501

Title: Anti-HIV compound assessment by two novel high capacity assays.

Journal: Journal of virological methods 19890301

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: Potentiating effect of ribavirin on the anti-retrovirus activity of 3'-azido-2,6-diaminopurine-2',3'-dideoxyriboside in vitro and in vivo.

Journal: Antiviral research 19890101

Title: 1',2'-seco-dideoxynucleosides as potential anti-HIV agents.

Journal: Journal of medicinal chemistry 19890101

Title: Marked in vivo antiretrovirus activity of 9-(2-phosphonylmethoxyethyl)adenine, a selective anti-human immunodeficiency virus agent.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19890101

Title: Nucleotide dimers suppress HIV expression in vitro.

Journal: AIDS research and human retroviruses 19881201

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: Inhibition of human immunodeficiency virus (HIV-1/HTLV-IIIBa-L) replication in fresh and cultured human peripheral blood monocytes/macrophages by azidothymidine and related 2',3'-dideoxynucleosides.

Journal: The Journal of experimental medicine 19880901

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

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

Title: Metabolism and anti-human immunodeficiency virus-1 activity of 2-halo-2',3'-dideoxyadenosine derivatives.

Journal: The Journal of biological chemistry 19880425

Title: Investigations on the anti-HIV activity of 2',3'-dideoxyadenosine analogues with modifications in either the pentose or purine moiety. Potent and selective anti-HIV activity of 2,6-diaminopurine 2',3'-dideoxyriboside.

Journal: Biochemical pharmacology 19880401

Title: Potent and selective activity of 3'-azido-2,6-diaminopurine-2',3'-dideoxyriboside, 3'-fluoro-2,6-diaminopurine-2',3'-dideoxyriboside, and 3'-fluoro-2',3'-dideoxyguanosine against human immunodeficiency virus.

Journal: Molecular 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: Synthesis and anti-HIV activity of various 2'- and 3'-substituted 2',3'-dideoxyadenosines: a structure-activity analysis.

Journal: Journal of medicinal chemistry 19871101

Title: Ribavirin antagonizes inhibitory effects of pyrimidine 2',3'-dideoxynucleosides but enhances inhibitory effects of purine 2',3'-dideoxynucleosides on replication of human immunodeficiency virus in vitro.

Journal: Antimicrobial agents and chemotherapy 19871001

Title: 2',3'-Dideoxy-2'-fluoro-ara-A. An acid-stable purine nucleoside active against human immunodeficiency virus (HIV).

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: The 2',3'-dideoxyriboside of 2,6-diaminopurine selectively inhibits human immunodeficiency virus (HIV) replication in vitro.

Journal: Biochemical and biophysical research communications 19870529

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

Journal: Journal of medicinal chemistry 19870501

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: Balzarini J, et al. Conversion of 2',3'-dideoxyadenosine (ddA) and 2',3'-didehydro-2',3'-dideoxyadenosine (d4A) to their corresponding aryloxyphosphoramidate derivatives markedly potentiates their activity against human immunodeficiency virus and hepatitis B virus. FEBS Lett. 1997 Jun 30;410(2-3):324-8.

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Tags:4097-22-7 Molecular Formula|4097-22-7 MDL|4097-22-7 SMILES|4097-22-7 2',3'-Dideoxyadenosine |Heterocyclic_Building_Blocks