Home Amines 606-58-6
606-58-6,MFCD00866513
Catalog No.:AA019FTP

606-58-6 | 4-Amino-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

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1mg
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5mg
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10mg
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25mg
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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:
AA019FTP
Chemical Name:
4-Amino-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
CAS Number:
606-58-6
Molecular Formula:
C12H13N5O4
Molecular Weight:
291.2627
MDL Number:
MFCD00866513
SMILES:
OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cc(c2c1ncnc2N)C#N
Properties
Properties
 
Form:
Solid  
MP:
>233ºC (dec.)  
Storage:
Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
443  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
21  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
2  
XLogP3:
-1.6  

Downstream Synthesis Route

[1]Heterocycles,1992,vol.33,p.391-404

[1]Patent:WO2010/135520,2010,A1.Locationinpatent:Page/Pagecolumn141-142

[1]Patent:WO2011/130599,2011,A1.Locationinpatent:Page/Pagecolumn69

Literature

Title: Interaction of Rio1 kinase with toyocamycin reveals a conformational switch that controls oligomeric state and catalytic activity.

Journal: PloS one 20120101

Title: Revealing the quaternary structure of a heterogeneous noncovalent protein complex through surface-induced dissociation.

Journal: Analytical chemistry 20110415

Title: 7-Deazapurine biosynthesis: NMR study of toyocamycin biosynthesis in Streptomyces rimosus using 2-13C-7-15N-adenine.

Journal: Organic & biomolecular chemistry 20110407

Title: Susceptibility in vitro of clinically metronidazole-resistant Trichomonas vaginalis to nitazoxanide, toyocamycin, and 2-fluoro-2'-deoxyadenosine.

Journal: Parasitology research 20100901

Title: Cell cycle arrest and cytochrome c-mediated apoptotic induction in human lung cancer A549 cells by MCS-C2, an analogue of sangivamycin.

Journal: Journal of microbiology and biotechnology 20100201

Title: Hydrogenosomes of laboratory-induced metronidazole-resistant Trichomonas vaginalis lines are downsized while those from clinically metronidazole-resistant isolates are not.

Journal: The Journal of eukaryotic microbiology 20100101

Title: A toyocamycin analogue with the sugar moiety in a syn conformation.

Journal: Acta crystallographica. Section C, Crystal structure communications 20090901

Title: Studies on the glycosylation of pyrrolo[2,3-d] pyrimidines with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose: the formation of regioisomers during toyocamycin and 7-deazainosine syntheses.

Journal: Nucleosides, nucleotides & nucleic acids 20090501

Title: Light-activation of gene function in mammalian cells via ribozymes.

Journal: Chemical communications (Cambridge, England) 20090207

Title: Toyocamycin specifically inhibits auxin signaling mediated by SCFTIR1 pathway.

Journal: Phytochemistry 20090101

Title: Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.

Journal: Journal of medicinal chemistry 20081113

Title: Deciphering deazapurine biosynthesis: pathway for pyrrolopyrimidine nucleosides toyocamycin and sangivamycin.

Journal: Chemistry & biology 20080825

Title: Functional expression of ribozymes in Apicomplexa: towards exogenous control of gene expression by inducible RNA-cleavage.

Journal: International journal for parasitology 20080501

Title: A CoMSIA study on the adenosine kinase inhibition of pyrrolo[2,3-d]pyrimidine nucleoside analogues.

Journal: Bioorganic & medicinal chemistry 20080501

Title: 7-deazainosine derivatives: synthesis and characterization of 7- and 7,8-substituted pyrrolo [2,3-d]pyrimidine ribonucleosides.

Journal: Nucleosides, nucleotides & nucleic acids 20080501

Title: Antineoplastic agents. 536. New sources of naturally occurring cancer cell growth inhibitors from marine organisms, terrestrial plants, and microorganisms(1a,).

Journal: Journal of natural products 20080301

Title: Synthesis of pyrrolo[2,3-d]pyrimidine nucleoside derivatives as potential anti-HCV agents.

Journal: Bioorganic chemistry 20070201

Title: Identification of inhibitors of ribozyme self-cleavage in mammalian cells via high-throughput screening of chemical libraries.

Journal: RNA (New York, N.Y.) 20060501

Title: Cell cycle arrest and apoptotic induction in LNCaP cells by MCS-C2, novel cyclin-dependent kinase inhibitor, through p53/p21WAF1/CIP1 pathway.

Journal: Cancer science 20060501

Title: Induction of apoptosis in human leukemia cells by MCS-C2 via caspase-dependent Bid cleavage and cytochrome c release.

Journal: Cancer letters 20050608

Title: Synthesis of 2'-beta-C-methyl toyocamycin and sangivamycin analogues as potential HCV inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20050201

Title: Exogenous control of mammalian gene expression through modulation of RNA self-cleavage.

Journal: Nature 20040923

Title: A TOPS-MODE approach to predict adenosine kinase inhibition.

Journal: Bioorganic & medicinal chemistry letters 20040621

Title: An improved total synthesis of triciribine: a tricyclic nucleoside with antineoplastic and antiviral properties.

Journal: Nucleosides, nucleotides & nucleic acids 20040101

Title: Induction of p16/INK4a gene expression and cellular senescence by toyocamycin.

Journal: Biological & pharmaceutical bulletin 20021001

Title: Inhibition of cyclin-dependent kinase 1 by purines and pyrrolo[2,3-d]pyrimidines does not correlate with antiviral activity.

Journal: Antimicrobial agents and chemotherapy 20020801

Title: QSAR study on adenosine kinase inhibition of pyrrolo[2,3-d]pyrimidine nucleoside analogues using the hansch approach.

Journal: Bioorganic & medicinal chemistry letters 20020325

Title: Drug-induced translocation of nucleolar proteins fused to green fluorescent protein.

Journal: Methods in molecular biology (Clifton, N.J.) 20020101

Title: Synthesis of pyrrolo[2,1-f][1,2,4]triazine C-nucleosides. Isosteres of sangivamycin, tubercidin, and toyocamycin.

Journal: Carbohydrate research 20010309

Title: Synthesis and cytotoxicity of 4'-C- and 5'-C-substituted toyocamycins.

Journal: Bioorganic & medicinal chemistry 20010101

Title: Synthesis of carbocyclic analogs of 2',3'-dideoxysangivamycin, 2',3'-dideoxytoyocamycin, and 2',3'-dideoxytriciribine.

Journal: Nucleosides, nucleotides & nucleic acids 20010101

Title: Synthesis of non-nucleoside analogs of toyocamycin, sangivamycin, and thiosangivamycin: the effect of certain 4- and 4,6-substituents on the antiviral activity of pyrrolo[2,3-d]pyrimidines.

Journal: Journal of medicinal chemistry 19960830

Title: Synthesis of non-nucleoside analogs of toyocamycin, sangivamycin, and ++thiosangivamycin: influence of various 7-substituents on antiviral activity.

Journal: Journal of medicinal chemistry 19960216

Title: Synthesis and antiproliferative and antiviral activity of 2'-deoxy-2'-fluoroarabinofuranosyl analogs of the nucleoside antibiotics toyocamycin and sangivamycin.

Journal: Journal of medicinal chemistry 19950929

Title: Synthesis and evaluation of certain thiosangivamycin analogs as potential inhibitors of cell proliferation and human cytomegalovirus.

Journal: Journal of medicinal chemistry 19950929

Title: Design, synthesis, and studies on the structure activity relationships of certain pyrrolo[2,3-d]pyrimidine nucleosides and structurally related analogs as potential antineoplastic and antiviral agents.

Journal: Farmaco (Societa chimica italiana : 1989) 19910101

Title: Arabinofuranosylpyrrolo[2,3-d]pyrimidines as potential agents for human cytomegalovirus infections.

Journal: Journal of medicinal chemistry 19901201

Title: Synthesis and antiviral activity of some 7-[(2-hydroxyethoxy)methyl]pyrazolo[3,4-d]pyrimidine analogues of sangivamycin and toyocamycin.

Journal: Journal of medicinal chemistry 19900701

Title: Broad-spectrum antiviral activities of neplanocin A, 3-deazaneplanocin A, and their 5'-nor derivatives.

Journal: Antimicrobial agents and chemotherapy 19890801

Title: Synthesis, cytotoxicity, and antiviral activity of certain 7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidine nucleosides related to toyocamycin and sangivamycin.

Journal: Journal of medicinal chemistry 19890701

Title: Pyrrolo[2,3-d]pyrimidine nucleosides as inhibitors of human cytomegalovirus.

Journal: Antimicrobial agents and chemotherapy 19870401

Title: Nucleic acid related compounds. 51. Synthesis and biological properties of sugar-modified analogues of the nucleoside antibiotics tubercidin, toyocamycin, sangivamycin, and formycin.

Journal: Journal of medicinal chemistry 19870301

Title: Xylotubercidin against herpes simplex virus type 2 in mice.

Journal: Antimicrobial agents and chemotherapy 19861101

Title: Antiviral activity of C-5 substituted tubercidin analogues.

Journal: Journal of medicinal chemistry 19840301

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Tags:606-58-6 Molecular Formula|606-58-6 MDL|606-58-6 SMILES|606-58-6 4-Amino-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile