32659-31-7

Usage

Uses

Deoxy Chlorocytarabine is a lipophilic DNA synthesis inhibitor and has antileukemic activity.

InChI:InChI=1/C9H12ClN3O4/c10-3-4-6(14)7(15)8(17-4)13-2-1-5(11)12-9(13)16/h1-2,4,6-8,14-15H,3H2,(H2,11,12,16)/t4-,6-,7+,8-/m1/s1

Upstream product

• 32659-29-3 <2R-(2α,3β,3aβ,9aβ)>-2-chloromethyl-2,3,3a,9a-tetrahydro-3-hydroxy-6-imino-6H-furo<2',3':4,5>oxazolo<3,2-a>pyrimidine hydrochloride 
• 31652-78-5 5'-chloro-5'-deoxycytidine 
• 69260-61-3 5'-chloro-5'-deoxy-2',3'-O-sulphinylcytidine hydrochloride 

Downstream Products

• 32830-01-6 4-Amino-1-(2,5-anhydro-β-D-arabinofuranosyl)pyrimidin-2(1H)-one 

Relevant academic research and scientific papers

REACTION OF NUCLEOSIDES WITH THIONYL CHLORIDE; PREPARATION OF THE DEOXY DERIVATIVES OF CYTIDINE AND ADENOSINE

On reaction of thionyl chloride with cytidine and adenosine in refluxing acetonitrile, the 5'-chloro-2',3'-sulphinyl derivatives I and VII are formed in a quantitative yield.On heating in dimethylformamide, compound I affords 5'-chloro-5'-deoxycyclocytidine (II) which is hydrolyzed in alkali to the arabinosyl derivative III; reduction of III with tributyltin hydride gives the 5'-deoxyarabinosyl derivative IV.The sulphinyl derivative I is hydrolyzed to 5'-chloro-5'-deoxycytidine (V) which is reduced to 5'-deoxycytidine (VI).Analogously, the sulphinyl derivative VII affords 5'-chloro-5'-deoxyadenosine (VIII) and the reduction of VIII gives 5'-deoxyadenosine (IX).Of these compounds, the 5'-chloro-5'-deoxyarabinosyl derivative as the only one shows an inhibitory effect towards the L1210 cell growth.