Home Nitriles 4-Amino-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

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

CAS No.:
606-58-6
Catalog Number:
AG019FWH
Molecular Formula:
C12H13N5O4
Molecular Weight:
291.2627
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Purity
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Product Description
Catalog Number:
AG019FWH
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
IUPAC Name:
4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile
InChI:
InChI=1S/C12H13N5O4/c13-1-5-2-17(11-7(5)10(14)15-4-16-11)12-9(20)8(19)6(3-18)21-12/h2,4,6,8-9,12,18-20H,3H2,(H2,14,15,16)/t6-,8-,9-,12-/m1/s1
InChI Key:
XOKJUSAYZUAMGJ-WOUKDFQISA-N
SMILES:
OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cc(c2c1ncnc2N)C#N
UNII:
L7995C4D7F
Properties
Complexity:
443  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
0
Exact Mass:
291.097g/mol
Formal Charge:
0
Heavy Atom Count:
21  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
291.267g/mol
Monoisotopic Mass:
291.097g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
150A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.6  
Literature
Title Journal
Interaction of Rio1 kinase with toyocamycin reveals a conformational switch that controls oligomeric state and catalytic activity. PloS one 20120101
Revealing the quaternary structure of a heterogeneous noncovalent protein complex through surface-induced dissociation. Analytical chemistry 20110415
7-Deazapurine biosynthesis: NMR study of toyocamycin biosynthesis in Streptomyces rimosus using 2-13C-7-15N-adenine. Organic & biomolecular chemistry 20110407
Susceptibility in vitro of clinically metronidazole-resistant Trichomonas vaginalis to nitazoxanide, toyocamycin, and 2-fluoro-2'-deoxyadenosine. Parasitology research 20100901
Cell cycle arrest and cytochrome c-mediated apoptotic induction in human lung cancer A549 cells by MCS-C2, an analogue of sangivamycin. Journal of microbiology and biotechnology 20100201
Hydrogenosomes of laboratory-induced metronidazole-resistant Trichomonas vaginalis lines are downsized while those from clinically metronidazole-resistant isolates are not. The Journal of eukaryotic microbiology 20100101
A toyocamycin analogue with the sugar moiety in a syn conformation. Acta crystallographica. Section C, Crystal structure communications 20090901
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. Nucleosides, nucleotides & nucleic acids 20090501
Light-activation of gene function in mammalian cells via ribozymes. Chemical communications (Cambridge, England) 20090207
Toyocamycin specifically inhibits auxin signaling mediated by SCFTIR1 pathway. Phytochemistry 20090101
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors. Journal of medicinal chemistry 20081113
Deciphering deazapurine biosynthesis: pathway for pyrrolopyrimidine nucleosides toyocamycin and sangivamycin. Chemistry & biology 20080825
Functional expression of ribozymes in Apicomplexa: towards exogenous control of gene expression by inducible RNA-cleavage. International journal for parasitology 20080501
A CoMSIA study on the adenosine kinase inhibition of pyrrolo[2,3-d]pyrimidine nucleoside analogues. Bioorganic & medicinal chemistry 20080501
7-deazainosine derivatives: synthesis and characterization of 7- and 7,8-substituted pyrrolo [2,3-d]pyrimidine ribonucleosides. Nucleosides, nucleotides & nucleic acids 20080501
Antineoplastic agents. 536. New sources of naturally occurring cancer cell growth inhibitors from marine organisms, terrestrial plants, and microorganisms(1a,). Journal of natural products 20080301
Synthesis of pyrrolo[2,3-d]pyrimidine nucleoside derivatives as potential anti-HCV agents. Bioorganic chemistry 20070201
Identification of inhibitors of ribozyme self-cleavage in mammalian cells via high-throughput screening of chemical libraries. RNA (New York, N.Y.) 20060501
Cell cycle arrest and apoptotic induction in LNCaP cells by MCS-C2, novel cyclin-dependent kinase inhibitor, through p53/p21WAF1/CIP1 pathway. Cancer science 20060501
Induction of apoptosis in human leukemia cells by MCS-C2 via caspase-dependent Bid cleavage and cytochrome c release. Cancer letters 20050608
Synthesis of 2'-beta-C-methyl toyocamycin and sangivamycin analogues as potential HCV inhibitors. Bioorganic & medicinal chemistry letters 20050201
Exogenous control of mammalian gene expression through modulation of RNA self-cleavage. Nature 20040923
A TOPS-MODE approach to predict adenosine kinase inhibition. Bioorganic & medicinal chemistry letters 20040621
An improved total synthesis of triciribine: a tricyclic nucleoside with antineoplastic and antiviral properties. Nucleosides, nucleotides & nucleic acids 20040101
Induction of p16/INK4a gene expression and cellular senescence by toyocamycin. Biological & pharmaceutical bulletin 20021001
Inhibition of cyclin-dependent kinase 1 by purines and pyrrolo[2,3-d]pyrimidines does not correlate with antiviral activity. Antimicrobial agents and chemotherapy 20020801
QSAR study on adenosine kinase inhibition of pyrrolo[2,3-d]pyrimidine nucleoside analogues using the hansch approach. Bioorganic & medicinal chemistry letters 20020325
Drug-induced translocation of nucleolar proteins fused to green fluorescent protein. Methods in molecular biology (Clifton, N.J.) 20020101
Synthesis of pyrrolo[2,1-f][1,2,4]triazine C-nucleosides. Isosteres of sangivamycin, tubercidin, and toyocamycin. Carbohydrate research 20010309
Synthesis and cytotoxicity of 4'-C- and 5'-C-substituted toyocamycins. Bioorganic & medicinal chemistry 20010101
Synthesis of carbocyclic analogs of 2',3'-dideoxysangivamycin, 2',3'-dideoxytoyocamycin, and 2',3'-dideoxytriciribine. Nucleosides, nucleotides & nucleic acids 20010101
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 of medicinal chemistry 19960830
Synthesis of non-nucleoside analogs of toyocamycin, sangivamycin, and ++thiosangivamycin: influence of various 7-substituents on antiviral activity. Journal of medicinal chemistry 19960216
Synthesis and antiproliferative and antiviral activity of 2'-deoxy-2'-fluoroarabinofuranosyl analogs of the nucleoside antibiotics toyocamycin and sangivamycin. Journal of medicinal chemistry 19950929
Synthesis and evaluation of certain thiosangivamycin analogs as potential inhibitors of cell proliferation and human cytomegalovirus. Journal of medicinal chemistry 19950929
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. Farmaco (Societa chimica italiana : 1989) 19910101
Arabinofuranosylpyrrolo[2,3-d]pyrimidines as potential agents for human cytomegalovirus infections. Journal of medicinal chemistry 19901201
Synthesis and antiviral activity of some 7-[(2-hydroxyethoxy)methyl]pyrazolo[3,4-d]pyrimidine analogues of sangivamycin and toyocamycin. Journal of medicinal chemistry 19900701
Broad-spectrum antiviral activities of neplanocin A, 3-deazaneplanocin A, and their 5'-nor derivatives. Antimicrobial agents and chemotherapy 19890801
Synthesis, cytotoxicity, and antiviral activity of certain 7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidine nucleosides related to toyocamycin and sangivamycin. Journal of medicinal chemistry 19890701
Pyrrolo[2,3-d]pyrimidine nucleosides as inhibitors of human cytomegalovirus. Antimicrobial agents and chemotherapy 19870401
Nucleic acid related compounds. 51. Synthesis and biological properties of sugar-modified analogues of the nucleoside antibiotics tubercidin, toyocamycin, sangivamycin, and formycin. Journal of medicinal chemistry 19870301
Xylotubercidin against herpes simplex virus type 2 in mice. Antimicrobial agents and chemotherapy 19861101
Antiviral activity of C-5 substituted tubercidin analogues. Journal of medicinal chemistry 19840301
Properties