N4-Chloroacetylcytosine arabinoside

N4-Chloroacetylcytosine arabinoside
Names
IUPAC name
N-[1-(β-D-Arabinofuranosyl)-2-oxo-1,2-dihydropyrimidin-4-yl]-2-chloroacetamide
Systematic IUPAC name
2-Chloro-N-{1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}acetamide
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C11H14ClN3O6/c12-3-7(17)13-6-1-2-15(11(20)14-6)10-9(19)8(18)5(4-16)21-10/h1-2,5,8-10,16,18-19H,3-4H2,(H,13,14,17,20)/t5-,8-,9+,10-/m1/s1
    Key: WEJWVQRPBCYTRE-STRWAFKBSA-N
  • InChI=1/C11H14ClN3O6/c12-3-7(17)13-6-1-2-15(11(20)14-6)10-9(19)8(18)5(4-16)21-10/h1-2,5,8-10,16,18-19H,3-4H2,(H,13,14,17,20)/t5-,8-,9+,10-/m1/s1
    Key: WEJWVQRPBCYTRE-STRWAFKBBD
  • c1cn(c(=O)nc1NC(=O)CCl)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O
Properties
C11H14ClN3O6
Molar mass 319.70 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N4-Chloroacetylcytosine arabinoside is a GABA agonist[1][dubious – discuss] and might be a pro-drug for cytosine arabinoside, a chemotherapy medication.[2]

  1. ^ Li, S; Zhang, Y; Liu, H; Yan, Y; Li, Y (2008). "Identification and expression of GABAC receptor in rat testis and spermatozoa". Acta Biochimica et Biophysica Sinica. 40 (8): 761–7. doi:10.1111/j.1745-7270.2008.00453.x. PMID 18685793.
  2. ^ M, Ariatti; PA, Jones. "N4-chloroacetylcytosine arabinoside--a possible pro-drug of cytosine arabinoside". Biochemistry international. 15 (6). Biochem Int. ISSN 0158-5231. PMID 3440022. Retrieved 2024-11-05.