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Pyrrolopyrimidine nucleosides and nucleotides

Description:

Nucleoside derivatives containing a ribose derivative which is n-glycosylated to a pyrrolopyrimidine. Also called deazapurine nucleosides, they are analogs of purine nucleosides with the N atom of the purine being replaced by a C atom at position 7.

Ancestors:

Organic compounds ⮕ Nucleosides, nucleotides, and analogues ⮕ Pyrrolopyrimidine nucleosides and nucleotides

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  1. (2R，3R，4S，5R)-2-(4-Amino-5-bromo-7H-pyrrolo[2，3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3，4-diol
    (2R，3R，4S，5R)-2-(4-Amino-5-bromo-7H-pyrrolo[2，3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3，4-diol
    CAS: 21193-80-6 PubChem CID: 97186 Formula: C11H13BrN4O4 Molecular Weight: 345.15
    ≥97%
    Out of Stock Item #: T695265
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    Technical Identifiers
    IUPAC Name
    (2R,3R,4S,5R)-2-(4-amino-5-bromopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
    SMILES
    C1=C(C2=C(N=CN=C2N1C3C(C(C(O3)CO)O)O)N)Br
    InChIKey
    ZWTPRQXZXQEKFT-IOSLPCCCSA-N
    InChI
    1S/C11H13BrN4O4/c12-4-1-16(10-6(4)9(13)14-3-15-10)11-8(19)7(18)5(2-17)20-11/h1,3,5,7-8,11,17-19H,2H2,(H2,13,14,15)/t5-,7-,8-,11-/m1/s1
  2. Jaspamycin
    Jaspamycin
    CAS: 22242-96-2 PubChem CID: 136670059 Formula: C12H12N4O5 Molecular Weight: 292.25
    ≥98%
    Out of Stock Item #: J647143
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    Technical Identifiers
    IUPAC Name
    7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-oxo-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
    SMILES
    C1=C(C2=C(N1C3C(C(C(O3)CO)O)O)N=CNC2=O)C#N
    InChIKey
    SKDKFLFSBDYEDO-WOUKDFQISA-N
    InChI
    1S/C12H12N4O5/c13-1-5-2-16(10-7(5)11(20)15-4-14-10)12-9(19)8(18)6(3-17)21-12/h2,4,6,8-9,12,17-19H,3H2,(H,14,15,20)/t6-,8-,9-,12-/m1/s1
  3. LLY-283 - , used for , CAS No. L611559, by Aladdin Scientific
    LLY-283
    Moligand™ ? Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools.
    Out of Stock Item #: L611559
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    Technical Identifiers
    IUPAC Name
    (2R,3R,4S,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-[(R)-hydroxy(phenyl)methyl]oxolane-3,4-diol
    SMILES
    O[C@@H]([C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1ccc2c1ncnc2N)c1ccccc1
    InChIKey
    WWOOWAHTEXIWBO-QFRSUPTLSA-N
    InChI
    1S/C17H18N4O4/c18-15-10-6-7-21(16(10)20-8-19-15)17-13(24)12(23)14(25-17)11(22)9-4-2-1-3-5-9/h1-8,11-14,17,22-24H,(H2,18,19,20)/t11-,12+,13-,14-,17-/m1show more
  4. Tubercidin
    Tubercidin
    CAS: 69-33-0 EC Number: 200-703-4 Formula: C11H14N4O4 Molecular Weight: 266.25
    Moligand™ ? Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools. ≥95% from Streptomyces tubercidicus
    Out of Stock Item #: T477619
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    Technical Identifiers
    IUPAC Name
    (2R,3R,4S,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
    SMILES
    C1=CN(C2=NC=NC(=C21)N)C3C(C(C(O3)CO)O)O
    InChIKey
    HDZZVAMISRMYHH-KCGFPETGSA-N
    InChI
    1S/C11H14N4O4/c12-9-5-1-2-15(10(5)14-4-13-9)11-8(18)7(17)6(3-16)19-11/h1-2,4,6-8,11,16-18H,3H2,(H2,12,13,14)/t6-,7-,8-,11-/m1/s1
    Synonyms
    7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine | 7-Deazaadenosine | 7-deaza-adenosine | AKOS024464517 | ...
  5. Sangivamycin
    Sangivamycin
    CAS: 18417-89-5 EC Number: 634-052-6 PubChem CID: 14978 Formula: C12H15N5O5 Molecular Weight: 309.28
    ≥98%
    In Stock Item #: S339041
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    Technical Identifiers
    IUPAC Name
    4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carboxamide
    SMILES
    C1=C(C2=C(N=CN=C2N1C3C(C(C(O3)CO)O)O)N)C(=O)N
    InChIKey
    OBZJZDHRXBKKTJ-JTFADIMSSA-N
    InChI
    1S/C12H15N5O5/c13-9-6-4(10(14)21)1-17(11(6)16-3-15-9)12-8(20)7(19)5(2-18)22-12/h1,3,5,7-8,12,18-20H,2H2,(H2,14,21)(H2,13,15,16)/t5-,7-,8-,12-/m1/s1
    Synonyms
    BRN 0626355 | 4-Amino-7-beta-D-ribofuranosyl-7H-pyrrolo(2,3-d)pyrimidine-5-carboxamide | 7H-Pyrrolo[2,3-d]pyrimidine-...
  6. NITD 008
    NITD 008
    CAS: 1044589-82-3 Formula: C13H14N4O4 Molecular Weight: 290.27
    ≥97%(HPLC)
    Out of Stock Item #: N286837
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    Technical Identifiers
    IUPAC Name
    (2R,3R,4R,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-3-ethynyl-5-(hydroxymethyl)oxolane-3,4-diol
    SMILES
    C#CC1(C(C(OC1N2C=CC3=C(N=CN=C32)N)CO)O)O
    InChIKey
    NKRAIOQPSBRMOV-NRMKKVEVSA-N
    InChI
    1S/C13H14N4O4/c1-2-13(20)9(19)8(5-18)21-12(13)17-4-3-7-10(14)15-6-16-11(7)17/h1,3-4,6,8-9,12,18-20H,5H2,(H2,14,15,16)/t8-,9-,12-,13-/m1/s1
    Synonyms
    7H-Pyrrolo(2,3-d)pyrimidin-4-amine, 7-(2-c-ethynyl-beta-D-ribofuranosyl)- | LKI7T3WQ2E | 1044589-82-3 | UNII-LKI7T3WQ...
  7. LLY-283 - Moligand™, ≥98% CAS No(2040291-27-6) by Aladdin Scientific
    LLY-283
    CAS: 2040291-27-6 Formula: C17H18N4O4 Molecular Weight: 342.35
    Moligand™ ? Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools. ≥98%
    In Stock Item #: L414243
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    Technical Identifiers
    IUPAC Name
    (2R,3R,4S,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-[(R)-hydroxy(phenyl)methyl]oxolane-3,4-diol
    SMILES
    C1=CC=C(C=C1)C(C2C(C(C(O2)N3C=CC4=C(N=CN=C43)N)O)O)O
    InChIKey
    WWOOWAHTEXIWBO-QFRSUPTLSA-N
    InChI
    1S/C17H18N4O4/c18-15-10-6-7-21(16(10)20-8-19-15)17-13(24)12(23)14(25-17)11(22)9-4-2-1-3-5-9/h1-8,11-14,17,22-24H,(H2,18,19,20)/t11-,12+,13-,14-,17-/m1show more
    Synonyms
    (2R,3R,4S,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-[(R)-hydroxy(phenyl)methyl]oxolane-3,4-diol
  8. LLY-283
    LLY-283
    CAS: 2040291-27-6 Formula: C17H18N4O4 Molecular Weight: 342.35
    Moligand™ ? Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools. 10mM in DMSO
    In Stock Item #: L422481
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    Technical Identifiers
    IUPAC Name
    (2R,3R,4S,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-[(R)-hydroxy(phenyl)methyl]oxolane-3,4-diol
    SMILES
    C1=CC=C(C=C1)C(C2C(C(C(O2)N3C=CC4=C(N=CN=C43)N)O)O)O
    InChIKey
    WWOOWAHTEXIWBO-QFRSUPTLSA-N
    InChI
    1S/C17H18N4O4/c18-15-10-6-7-21(16(10)20-8-19-15)17-13(24)12(23)14(25-17)11(22)9-4-2-1-3-5-9/h1-8,11-14,17,22-24H,(H2,18,19,20)/t11-,12+,13-,14-,17-/m1show more
    Synonyms
    (2R,3R,4S,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-[(R)-hydroxy(phenyl)methyl]oxolane-3,4-diol
  9. 7-Deazaadenosine (Tubercidin)
    7-Deazaadenosine (Tubercidin)
    CAS: 69-33-0 EC Number: 200-703-4 Formula: C11H14N4O4 Molecular Weight: 266.25
    Moligand™ ? Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools. 10mM in DMSO
    In Stock Item #: D425559
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    Technical Identifiers
    IUPAC Name
    (2R,3R,4S,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
    SMILES
    C1=CN(C2=NC=NC(=C21)N)C3C(C(C(O3)CO)O)O
    InChIKey
    HDZZVAMISRMYHH-KCGFPETGSA-N
    InChI
    1S/C11H14N4O4/c12-9-5-1-2-15(10(5)14-4-13-9)11-8(18)7(17)6(3-16)19-11/h1-2,4,6-8,11,16-18H,3H2,(H2,12,13,14)/t6-,7-,8-,11-/m1/s1
    Synonyms
    7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine | 7-Deazaadenosine | 7-deaza-adenosine | AKOS024464517 | ...
  10. 6-Chloro-7-deazapurine-β-D-riboside
    6-Chloro-7-deazapurine-β-D-riboside
    CAS: 16754-80-6 Formula: C11H12ClN3O4 Molecular Weight: 285.68
    ≥98%
    In Stock Item #: C332800
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    Technical Identifiers
    IUPAC Name
    (2R,3R,4S,5R)-2-(4-chloropyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
    SMILES
    C1=CN(C2=C1C(=NC=N2)Cl)C3C(C(C(O3)CO)O)O
    InChIKey
    BFDDOTZWMOKUCD-KCGFPETGSA-N
    InChI
    1S/C11H12ClN3O4/c12-9-5-1-2-15(10(5)14-4-13-9)11-8(18)7(17)6(3-16)19-11/h1-2,4,6-8,11,16-18H,3H2/t6-,7-,8-,11-/m1/s1
    Synonyms
    (2R,3R,4S,5R)-2-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
  11. 5-Iodotubercidin
    5-Iodotubercidin
    CAS: 24386-93-4 EC Number: 194-755-4 Formula: C11H13IN4O4 Molecular Weight: 392.15
    10mM in DMSO
    In Stock Item #: I422822
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    (2R,3R,4S,5R)-2-(4-amino-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
    SMILES
    C1=C(C2=C(N=CN=C2N1C3C(C(C(O3)CO)O)O)N)I
    InChIKey
    WHSIXKUPQCKWBY-IOSLPCCCSA-N
    InChI
    1S/C11H13IN4O4/c12-4-1-16(10-6(4)9(13)14-3-15-10)11-8(19)7(18)5(2-17)20-11/h1,3,5,7-8,11,17-19H,2H2,(H2,13,14,15)/t5-,7-,8-,11-/m1/s1
    Synonyms
    (2R,3R,4S,5R)-2-(4-amino-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol | A848734 | BDBM503756...
  12. 6-Chloro-7-deazapurine-α-D-riboside - 95%, used for , CAS No. 120401-32-3, by Aladdin Scientific
    6-Chloro-7-deazapurine-α-D-riboside
    CAS: 120401-32-3 Formula: C11H12ClN3O4 Molecular Weight: 285.69
    ≥95%
    In Stock Item #: C348488
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    (2R,3R,4S,5R)-2-(4-chloropyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
    SMILES
    C1=CN(C2=C1C(=NC=N2)Cl)C3C(C(C(O3)CO)O)O
    InChIKey
    BFDDOTZWMOKUCD-KCGFPETGSA-N
    InChI
    1S/C11H12ClN3O4/c12-9-5-1-2-15(10(5)14-4-13-9)11-8(18)7(17)6(3-16)19-11/h1-2,4,6-8,11,16-18H,3H2/t6-,7-,8-,11-/m1/s1
    Synonyms
    4-Chloro-7-α-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine
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