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5,6-Dichloro-1-β-D-ribofuranosylbenzimidazole

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5,6-Dichloro-1-β-D-ribofuranosylbenzimidazole
Names
IUPAC name 5,6-Dichloro-1-(β-D-ribofuranosyl)-1H-1,3-benzimidazole
Systematic IUPAC name (2R,3R,4S,5R)-2-(5,6-Dichloro-1H-1,3-benzimidazol-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Other names DRB, Dichlororibofuranosylbenzimidazole
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
IUPHAR/BPS
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C12H12Cl2N2O4/c13-5-1-7-8(2-6(5)14)16(4-15-7)12-11(19)10(18)9(3-17)20-12/h1-2,4,9-12,17-19H,3H2/t9-,10-,11-,12-/m1/s1Key: XHSQDZXAVJRBMX-DDHJBXDOSA-N
  • InChI=1/C12H12Cl2N2O4/c13-5-1-7-8(2-6(5)14)16(4-15-7)12-11(19)10(18)9(3-17)20-12/h1-2,4,9-12,17-19H,3H2/t9-,10-,11-,12-/m1/s1Key: XHSQDZXAVJRBMX-DDHJBXDOBF
SMILES
  • Clc2cc1ncn(c1cc2Cl)3O((O)3O)CO
Properties
Chemical formula C12H12Cl2N2O4
Molar mass 319.14 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

5,6-Dichloro-1-β-D-ribofuranosylbenzimidazole (DRB) is a chemical compound that inhibits transcription elongation by RNA Polymerase II. Sensitivity to DRB is dependent on DRB sensitivity inducing factor (DSIF), negative elongation factor (NELF), and positive transcription elongation factor b (P-TEFb). DRB is a nucleoside analog and also inhibits some protein kinases.

References

  1. Yamaguchi, Y.; Takagi, T.; Wada, T.; Yano, K.; Furuya, A.; Sugimoto, S.; Hasegawa, J.; Handa, H. (1999). "NELF, a Multisubunit Complex Containing RD, Cooperates with DSIF to Repress RNA Polymerase II Elongation". Cell. 97 (1): 41–51. doi:10.1016/S0092-8674(00)80713-8. PMID 10199401.


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