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1-(β-D-Arabinofuranosyl)-4-O-difluoromethyluracil is a modified nucleoside analogue derived from arabinofuranosyluracil (araU), where a difluoromethyl group is introduced at the 4-O position. This modification, achieved through a CF2-insertion reaction, retains antiviral activity against herpes simplex viruses (HSV-1 and HSV-2) compared to other nucleoside analogues like 2'-deoxyuridine derivatives, which show reduced efficacy. Certain 4,5-disubstituted variants of 1-(beta-d-Arabinofuranosyl)-4-O-difluoromethyluracil exhibit selective and potent anti-HSV-1 activity, with some demonstrating broad-spectrum inhibition comparable to reference drugs like acyclovir and araT.

102302-66-9

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102302-66-9 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 102302-66-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,2,3,0 and 2 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 102302-66:
(8*1)+(7*0)+(6*2)+(5*3)+(4*0)+(3*2)+(2*6)+(1*6)=59
59 % 10 = 9
So 102302-66-9 is a valid CAS Registry Number.

102302-66-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-β-D-arabinofuranosyl-4-O-(difluoromethyl)uracil

1.2 Other means of identification

Product number -
Other names 4-Difluoromethoxy-1-((2R,3S,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:102302-66-9 SDS

102302-66-9Downstream Products

102302-66-9Relevant academic research and scientific papers

ZUR SYNTHESE VON DIFLUOROMETHYLETHERN VERSHIEDEN SUBSTITUIERTER PYRIMIDINNUCLEOSIDE DURCH REAKTION MIT DIFLUORCARBEN

Pein, C.-D.,Cech, D.

, p. 4915 - 4918 (1985)

The reaction of CF2 with different substituted persilylated pyrimidine nucleosides either in the ribo-, 2'-deoxyribo- or in the arabino-series gave the corresponding 4-O-difluoromethylethers.Optimum yields were obtained using Hg(CF3)2 as source of CF2.

Synthesis and biological activities of 4-O-(difluoromethyl)-5-substituted-uracil nucleoside analogues

Reefschlager,Pein,Cech

, p. 393 - 397 (1988)

Various 4-O-difluoromethyl analogues of 5-substituted uridine (Urd),2'-deoxyuridine (dUrd), and arabinofuranosyluracil (araU) nucleosides were prepared via a CF2-insertion reaction into 4-O-silylated nucleosides and evaluated for activity against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) and cytotoxicity in human embryonic lung fibroblast (HELF) cell cultures. The introduction of the 4-substituent led to a strong reduction of antiviral activity for dUrd but not for araU analogues. Three of the 4,5-disubstituted uracil nucleoside derivatives, 4-O-(difluoromethyl)-5-bromo-araU (5c), -5-methyl-araU (5e), and -(E)-5-(2-bromovinyl)-araU (5g), displayed a high and selective inhibitory effect against HSV-1, but only 5e was effective against both HSV-1 and HSV-2 comparably with the antiherpes potential of the reference compounds 9-[(2-hydroxyethoxy)methyl]guanine (acyclovir) and 1-β-D-arabinofuranosylthymine (araT).

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