3590-48-5

Usage

Uses

Used in Pharmaceutical Industry:
5-(Chloromethyl)uracil is used as an antitumor agent for its potential to inhibit thymidylate synthase, a key enzyme in DNA synthesis, thereby disrupting the growth of tumor cells.
Used in Antiviral Applications:
5-(Chloromethyl)uracil is used as an antiviral agent due to its ability to interfere with viral replication processes, potentially inhibiting the spread of viruses within host cells.
Used in Antifungal Applications:
5-(Chloromethyl)uracil is used as an antifungal agent to combat fungal infections by targeting essential processes within fungal cells, thereby preventing their growth and spread.
Used in Agricultural Industry:
5-(Chloromethyl)uracil is used in agriculture to control the growth of fungi and viruses that can harm crops, thereby protecting agricultural yields and ensuring food security.

InChI:InChI=1/C5H5ClN2O2/c6-1-3-2-7-5(10)8-4(3)9/h2H,1H2,(H2,7,8,9,10)

Upstream product

• 4433-40-3 5-hydroxymethyl uracil 

Downstream Products

• 89179-86-2 5-(aminomethyl)-2,4(1H,3H)-pyrimidinedione 
• 82949-83-5 5,10-bis(uracil-5-ylmethyl)tetrahydropteroylglutamic acid 
• 84345-62-0 5-<(1-phenyl-5-thioxo-2-tetrazolin-4-yl)methyl>uracil 
• 84345-57-3 5-<<(1-phenyl-1,2,3,4-tetrazol-5-yl)thio>methyl>uracil 
• 4433-40-3 5-hydroxymethyl uracil 
• 88459-62-5 5-<(2-hydroxyethoxy)methyl>uracil 
• 89000-17-9 5-(4-bromophenylthiomethyl)uracil 
• 118202-60-1 N-(5-Uracyl)methyl-2-phenylisopropylamine 
• 84345-64-2 5-(5-Phenyl-[1,3,4]oxadiazol-2-ylsulfanylmethyl)-1H-pyrimidine-2,4-dione 
• 84345-65-3 5-(5-Phenyl-2-thioxo-[1,3,4]oxadiazol-3-ylmethyl)-1H-pyrimidine-2,4-dione 
• 75689-16-6 10-methyl-5-(uracil-5-ylmethyl)tetrahygropteroylglutamic acid 
• 82883-90-7 10-methyl-5-(uracil-5-ylmethyl)<6-2H¹>tetrahygropteroylglutamic acid 
• 4874-41-3 5-Ethyl-thiomethyl-uracil 
• 57346-43-7 5-(methoxymethyl)pyrimidine-2,4-diol 

Relevant academic research and scientific papers

Improved nucleic acid triggered probe activation through the use of a 5-thiomethyluracil peptide nucleic acid building block

(Chemical Equation Presented) To improve the efficiency of a nucleic acid triggered probe activation (NATPA) system a 5-thiomethyluracil peptide nucleic acid (PNA) building block has been synthesized. Attachment of imidazole and a coumarin ester to uracils at the ends of two PNAs resulted in a 550 000-fold acceleration of DNA-triggered coumarin release relative to imidazole and a 6-fold increase in kcat relative to a system which had these groups attached to the amino and carboxy ends of PNAs.

Uracil-bearing poly(2-isopropyl-2-oxazoline): Hg(II)-selective control of its thermoresponsiveness

A poly(2-isopropyl-2-oxazoline)-containing mercury ion (Hg2+)-responsive uracil moiety (U-PiPOx-U) was synthesized and it exhibited thermoresponsiveness in its aqueous solution. The changes in the UV-Vis absorption and thermoresponsiveness of U-PiPOx-U upon the addition of Hg2+ were studied. Selective sensing of Hg2+ was also investigated.

Synthesis and Spectroscopy of Phosphonate Derivatives of Uracil and Thymine. X-Ray Crystal Structure of Diethyl 6-Uracilmethylphosphonate

A new class of phosphonate ligands, derived from uracil and thymine was designed, prepared and characterised. Dimethyl (4, 7) and diethyl (5, 8) uracilmethylphosphonates have been prepared by the reaction of chloromethyluracil isomers 2 and 3 with trimethyl phosphite and triethyl phosphite, respectively. The corresponding free acids, 5-uracilmethylphosphonic acid 6 and 6-uracilmethylphosphonic acid 9, have also been isolated. The structure of the compounds has been assigned by nmr spectroscopy and, in the case of 8, confirmed by X-ray analysis.

Thymidylate synthase inspired biomodel reagent for the conversion of uracil to thymine

Inspired by TSase catalysis for dUMP conversion to dTMP, a biomodel reagent is developed. The presence of NH2, Gly-(S)-Cys and (S)-oxiran methyl, at C5, C4 and N-10 of acridine, respectively, in addition to the pH of the reaction mixture, allows for good complementary inter- and intra-molecular interactions and chiral discrimination for the reagent to achieve conversion of uracil to thymine.

C(5) modified uracil derivatives showing antiproliferative and erythroid differentiation inducing activities on human chronic myelogenous leukemia K562 cells

The K562 cell line has been proposed as a useful experimental system to identify anti-tumor compounds acting by inducing terminal erythroid differentiation. K562 cells exhibit a low proportion of hemoglobin-synthesizing cells under standard cell growth conditions, but are able to undergo terminal erythroid differentiation when treated with a variety of anti-tumor compounds. In this paper we report a screening study on a set of different modified C(5) uracil derivatives for the evaluation of their antiproliferative effect in connection with erythroid differentiation pathways, and for defining a new class of drug candidates for the treatment of chronic myelogenous leukemia. Activity of the derivatives tested can be classified in two effect: an antiproliferative effect linked to a high level of erythroid differentiation activity and an antiproliferative effect without activation of gamma globin genes The highest antiproliferative effect and erythroid induction was shown by compound 9, a thymine derivative bearing a n-octyl chain on nitrogen N(1), whereas thymine did not show any effect, suggesting the importance of the linear alkyl chain in position N(1). To our knowledge this compound should be considered among the most efficient inducers of erythroid differentiation of K562 cells. This work is the starting point for the quest of more effective and specific drugs for the induction of terminal erythroid differentiation, for leading new insights in the treatment of neoplastic diseases with molecules acting by inducing differentiation rather than by simply exerting cytotoxic effects.

Uracil derivatives as inhibitors of TNF-alpha converting enzyme (TACE) and matrix metalloproteinases

The present application describes novel uracil derivatives of formula I: A-W-U-X-Y-Z-Ua-Xa-Ya-Za??I or pharmaceutically acceptable salt or prodrug forms thereof, wherein A, W, U, X, Y, Z, Ua, Xa, Ya, and Za are defined in the present specification, which are useful as inhibitors of TNF-α converting enzyme (TACE), matrix metalloproteinases (MMP), aggrecanase or a combination thereof.

Mechanistic studies on the repair of a novel DNA photolesion: The spore photoproduct

(matrix presented) UV irradiation of spores results in the formation of the spore photoproduct. This novel DNA photolesion is repaired in the germinating spore in a reaction catalyzed by the spore photoproduct lyase. Model studies, using a simple bispyrim

5-Ethylthiomethyl- and 5-Ethylsulfonylmethylpyrimidines

In 2,4-dichloro-5-ethylthiomethylpyrimidines 3a,b and in (2,4-dichloro-5-pyrimidinylmethyl)ethyl sulfones 5a,b, resp., by reaction with ammonia, diethylamine, isopropylamine, sodium methanolate and sodium ethylthiolate, resp., the halogen atoms have been substituted by amino, methoxy or ethylthio groups, resp., and thus the compounds 4a-4r and 5c-5f have been obtained.Keywords: Halogen exchange, in pyrimidines; Pyrimidines, 5-ethylsulfonyl-methyl-; Pyrimidines, 5-ethylthiomethyl-