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
CAS Number	113737-52-3;
3D model (JSmol)	Interactive image;
ChemSpider	2338731;
PubChem CID	3081042;
CompTox Dashboard (EPA)	DTXSID00921180 ;
	InChI 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;
	SMILES c1cn(c(=O)nc1NC(=O)CCl)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O;
Properties
Chemical formula	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). verify (what is ?) Infobox references

N⁴-Chloroacetylcytosine arabinoside is a GABA agonist^[1]^{[dubious – discuss]} and might be a pro-drug for cytosine arabinoside, a chemotherapy medication.^[2]

References

^ 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.
^ 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.

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