103782-15-6

Basic information

• Product Name: Uridine, 2'-deoxy-5-fluoro-3'-O-[(4-fluorophenyl)methyl]-
• CAS NO: 103782-15-6
• Molecular Formula: C16H16F2N2O5
• Molecular Weight: 354.31
• Mol File: 103782-15-6.mol

Chemical Properties

• CAS DataBase Reference: Uridine, 2'-deoxy-5-fluoro-3'-O-[(4-fluorophenyl)methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Uridine, 2'-deoxy-5-fluoro-3'-O-[(4-fluorophenyl)methyl]-(103782-15-6)
• EPA Substance Registry System: Uridine, 2'-deoxy-5-fluoro-3'-O-[(4-fluorophenyl)methyl]-(103782-15-6)

Safety Data

• Hazardous Substances Data: 103782-15-6(Hazardous Substances Data)

Upstream product

• 352-11-4 1-chloromethyl-4-fluorobenzene 
• 50-91-9 5-Fluoro-2'-deoxyuridine 
• 459-46-1 4-Fluorobenzyl bromide 
• 129816-30-4 5'-O-(tert-butyldimethylsilyl)-2'-deoxy-5-fluorouridine 
• 1054661-93-6 5-Fluoro-1-[(2R,4S,5R)-4-(4-fluoro-benzyloxy)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 

Downstream Products

• 179744-33-3 (S)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid 5-fluoro-3-[(2R,4S,5R)-4-(4-fluoro-benzyloxy)-5-hydroxymethyl-tetrahydro-furan-2-yl]-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl ester 

Relevant articles and documents

Synthesis and antitumor activities of 5′-O-aminoacyl-3′-O-benzyl derivatives of 2′-deoxy-5-fluorouridine and related compounds

Various O-alkyl derivatives of 2′-deoxy-5-fluorouridine (FUdR) were synthesized and their antitumor activities in mice bearing sarcoma 180 (s.c.-p.o.) were evaluated in terms of the ED50 values (mg/kg/d). Most of these compounds were superior to FUdR in antitumor activity. In particular, the antitumor activity of 3′-O-(p-chlorobenzyl)-FUdR (3e) (ED50 = 0.87 mg/kg/d) was as much as 100 times that of FUdR (ED50 = 84 mg/kg/d). Further, various 5′-O-aminoacyl derivatives of 3e were synthesized and evaluated in terms of ED50 value and therapeutic index (T.I.). Both the ED50 value (0.41 mg/kg/d) and the T.I. (4.18) of 3′-O-(p-chlorobenzyl)-5′-O-glycyl-FUdR hydrochloride (6a) were significantly improved, compared with those of 3e and FUdR. FUdR plasma concentration after a single p.o. dosing of 6a was maintained for as long as 24 h.

Synthesis and biological activity of O-alkyl-3-N-aminoacyloxymethyl-5- fluoro-2'-deoxyuridine derivatives

In an attempt to improve the effectiveness of action of 5-fluoro-2'- deoxyuridine (FUdR), various kinds of O-alkylated water-soluble analogues were synthesized. Antitumor activities against sarcoma 180 (solid) were also evaluated. Some compounds exhibited potent activities. In particular, 3'-O- p-chlorobenzyl-3-N-aminoacyloxy-methylester derivatives were effective over a very wide range of dose and gave extremely large therapeutic ratios compared with known 5-fluorouracil (5-FU) derivatives.

5-fluorouracil derivatives

An anticancer compound is disclosed which is represented by the formula STR1 wherein one of R1 and R2 is a phenyl-lower alkyl optionally having a substituent, phenyl-lower alkenyl or naphthyl-lower alkyl, the other of R1 and R2 is hydrogen or acyl, and R3 is hydrogen, acyl or tetrahydrofuranyl, or represented by the formula STR2 wherein Rx is an optionally substituted pyridyl, Y is arylene and α is a known 5-fluorouracil derivative residue which can be converted to 5-fluorouracil in vivo and which is linked to the carbonyl by an ester or amide linkage.