69260-69-1

Usage

Type

Synthetic nucleoside analog

Antineoplastic Activity

Potential

Prodrug of

5-fluorouracil (5-FU)

Mechanism of Action

Inhibits thymidylate synthase and interferes with DNA synthesis

Effect on Cells

Leads to cell death

Cancer Types Treated

Colorectal, breast, and head and neck cancers

Current Research

Being studied in combination with other chemotherapy agents and targeted therapies for potential in cancer treatment.

Upstream product

• 58-96-8 uridine 
• 86286-91-1 5'-chloro-O^2'_,O3'-sulfinyl-5'-deoxy-uridine 

Downstream Products

• 136721-70-5 5'-S-(4-methoxyphenyl)-5'-thiouridine 
• 136721-71-6 5'-S-(4-hydroxyphenyl)-5'-thiouridine 
• 132628-21-8 1-{(2R,3R,4S,5S)-3,4-Dihydroxy-5-[9-(4-methoxy-phenyl)-9H-xanthen-9-ylsulfanylmethyl]-tetrahydro-furan-2-yl}-1H-pyrimidine-2,4-dione 
• 119220-31-4 1-(5-deoxy-5-phenylthio-β-D-arabinofuranosyl)uracil 

Relevant academic research and scientific papers

Chlorination of nucleosides by N-chlorodiisopropylamine and triphenylphosphine

The combination of N-chlorodiisopropylamine and triphenylphosphine (1) was exploited as a new method for chlorination of the hydroxyl group on the nucleosides. A possible mechanism involving an oxyphosphonium intermediate 2a and a phosphorane intermediate 2b was proposed based on the results from 31P NMR spectrum.

9-(4-METHOXYPHENYL)XANTHEN-9-THIOL: A USEFUL REAGENT FOR THE PREPARATION OF THIOLS

Treatment of 5'-chloro-5'-deoxynucleosides (5) with the conjugate base of 9-(4-methoxyphenyl)xanthen-9-thiol (3b), followed by acid-promoted removal of the 5'-S- group in the presence of pyrrole gives the corresponding 5'-deoxy-5'-mercaptonucleosides (7) in good yields.