cas 51-20-7, 5-Bromouracil | Articles data

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Free radicals in irradiated single crystals of 5-halo-uracil derivatives: 5-bromouracil, 5-bromodeoxyuridine and 5-iododeoxyuridine.
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Hüttermann,Müller
p. 297 - 313
(1969)
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Carbonic anhydrase inhibitory properties of some uracil derivatives
Inhibitors of carbonic anhydrase (CA) have been carried out in many therapeutic applications, especially antiglaucoma activity. In this study, we investigated some uracil derivatives (4–12) to inhibit human CA I (hCA I) and II (hCA II) isoenzymes. The KI values of the compounds 4–12 are in the range of 0.085–428 μM for hCA I and of 0.1715–645 μM against hCA II, respectively. It is concluded from the kinetic investigations, all compounds used in the study act as competitive inhibitors with substrate, 4-NPA. Uracil derivatives are emerging agents for the inhibiton of carbonic anhydrase which could be used in biomedicine.
Alper Türko?lu, Emir,?entürk, Murat,Supuran, Claudiu T.,Ekinci, Deniz
p. 74 - 77
(2017)
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Moore,Anderson
p. 590,591
(1959)
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Riederer et al.
p. 313
(1978)
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The discovery of a potent and selective pyrazolo-[2,3-e]-[1,2,4]-triazine cannabinoid type 2 receptor agonist
The development of selective CB2 receptor agonists is a promising therapeutic approach for the treatment of inflammatory diseases, without CB1 receptor mediated psychoactive side effects. Preliminary structure-activity relationship studies on pyrazoylidene benzamide agonists revealed the -ylidene benzamide moiety was crucial for functional activity at the CB2 receptor. A small library of compounds with varying linkage moieties between the pyrazole and substituted phenyl group has culminated in the discovery of a potent and selective pyrazolo-[2,3-e]-[1,2,4]-triazine agonist 19 (CB2R EC50 = 19 nM, CB1R EC50 > 10 μM). Docking studies have revealed key structural features of the linkage group that are important for potent functional activity.
Moir, Michael,Lane, Samuel,Montgomery, Andrew P.,Hibbs, David,Connor, Mark,Kassiou, Michael
(2020/12/21)

The synthesis and antituberculosis activity of 5-alkynyl uracil derivatives
A series of new 5-alkynyl-substituted uracil and uridine derivatives were synthesised via palladium-catalysed Sonogashira cross-coupling reaction of 5-bromo-pyrimidine base with terminal acetylenes with good yields in DMF at room temperature. All obtained compounds were tested for antimycobacterial activity against Mycobacetrium bovis and Mycobacterium tuberculosis (H37Ra) at concentrations of 1–100 μg/ml using MABA test. Obtained results revealed that most of tested uracil derivatives exhibited high antimycobacterial activity (MIC50 = 1.1–19.2 μg/ml) in comparison with therapeutic agents such as rifampicin, isoniazid and D-cycloserine, excluding compounds having alkyl substituent at triple alkyne bond.
Platonova, Yana B.,Tomilova, Larisa G.,Volov, Alexander N.
(2020/06/26)

Thermodynamic Reaction Control of Nucleoside Phosphorolysis
Nucleoside analogs represent a class of important drugs for cancer and antiviral treatments. Nucleoside phosphorylases (NPases) catalyze the phosphorolysis of nucleosides and are widely employed for the synthesis of pentose-1-phosphates and nucleoside analogs, which are difficult to access via conventional synthetic methods. However, for the vast majority of nucleosides, it has been observed that either no or incomplete conversion of the starting materials is achieved in NPase-catalyzed reactions. For some substrates, it has been shown that these reactions are reversible equilibrium reactions that adhere to the law of mass action. In this contribution, we broadly demonstrate that nucleoside phosphorolysis is a thermodynamically controlled endothermic reaction that proceeds to a reaction equilibrium dictated by the substrate-specific equilibrium constant of phosphorolysis, irrespective of the type or amount of NPase used, as shown by several examples. Furthermore, we explored the temperature-dependency of nucleoside phosphorolysis equilibrium states and provide the apparent transformed reaction enthalpy and apparent transformed reaction entropy for 24 nucleosides, confirming that these conversions are thermodynamically controlled endothermic reactions. This data allows calculation of the Gibbs free energy and, consequently, the equilibrium constant of phosphorolysis at any given reaction temperature. Overall, our investigations revealed that pyrimidine nucleosides are generally more susceptible to phosphorolysis than purine nucleosides. The data disclosed in this work allow the accurate prediction of phosphorolysis or transglycosylation yields for a range of pyrimidine and purine nucleosides and thus serve to empower further research in the field of nucleoside biocatalysis. (Figure presented.).
Kaspar, Felix,Giessmann, Robert T.,Neubauer, Peter,Wagner, Anke,Gimpel, Matthias
supporting information
p. 867 - 876
(2020/01/24)

A 5 - bromo uracil preparation method
The invention discloses a preparation method for 5-bromouracil. By taking uracil as an initial raw material, sodium bromide and sodium hypochlorite as a green bromating agent, and water as a solvent, a mild brominating reaction is carried out under an acidic condition to obtain a high purity target product. The preparation method disclosed by the invention is green and environmental-friendly in synthetic process, convenient in post-treatment and suitable for large-scaled industrial production.
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Paragraph 0033-0040

(2019/10/04)

Inhibition of acetylcholinesterase and butyrylcholinesterase with uracil derivatives: kinetic and computational studies
Acetylcholinesterase (AChE) and Butyrylcholinesterase (BuChE) inhibitors are interesting compounds for different therapeutic applications, among which Alzheimer’s disease. Here, we investigated the inhibition of these cholinesterases with uracil derivatives. The mechanism of inhibition of these enzymes was observed to be due to obstruction of the active site entrance by the inhibitors scaffold. Molecular docking and molecular dynamics (MD) simulations demonstrated the possible key interactions between the studied ligands and amino acid residues at different regions of the active sites of AChE and BuChE. Being diverse of the classical AChE and BuChE inhibitors, the investigated uracil derivatives may be used as lead molecules for designing new therapeutically effective enzyme inhibitors.
Cavdar, Huseyin,Senturk, Murat,Guney, Murat,Durdagi, Serdar,Kayik, Gulru,Supuran, Claudiu T.,Ekinci, Deniz
p. 429 - 437
(2019/01/14)

Preparation method for 5-bromouracil
The invention discloses a preparation method for 5-bromouracil. According to the preparation method, uracil is used as a raw material and reacts with a bromination reagent under the action of acid oracid/anhydride, wherein the the bromination reagent is 1,3-dibromo-5,5-dimethylhydantoin; the acid/anhydride refers to a mixture of acid and anhydride; the acid or acid in the acid/anhydride is organic acid; and the anhydride is organic acid anhydride.
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Paragraph 0025; 0026; 0030; 0032; 0034; 0036; 0042; 0044

(2018/08/04)

Preparation method for halogenated uracil compounds
The invention discloses a preparation method for halogenated uracil compounds as shown in a formula 2 which is described in the specification. The preparation method comprises a step of subjecting a compound 1 and PCl5 to a chlorination reaction in a solvent. X in the formula is F, Cl, Br or I. The solvent is one or more selected from a group consisting of SOCl2, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane, trichloroethylene and 1,1,2-trichloroethane. The preparation method uses 5-halouracil as a starting material, and is simple in process, high in yield, friendly to environment and suitable for industrial production.
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Paragraph 0046; 0047; 0050; 0052; 0054; 0056; 0068; 0070

(2018/08/04)

Solid-supported synthesis of N-alkylated derivatives of 5-bromo pyrimidine-2, 4-dione and Study of their cytotoxic effect
The presented study reports the synthesis of 5-bromo substituted pyrimidine-2,4-dione by conventional and solid-state microwave-assisted methodology. 5-bromo pyrimidine-2,4-dione derivatives represent the novel group of compounds possessing remarkable anti-tumor and antibacterial activities with significant therapeutic effects such as anti-neoplastic as well. Thus, a diversity-oriented convergent synthesis of complex organic molecules from simple and readily available substrates has been carried out that has resulted in the derivatization of 5-bromo pyrimidine-2,4 dione predominately giving N1 and N3 substituted compounds where R may be the alkyl, aryl, cyclohexyl methyl etc. In addition, use of solid-state microwave-assisted protocol proved to be of vital importance in terms of energy efficiency and designing a solvent-free ecofriendly synthetic route with considerably reduced reaction time.
Sagheer, Tahira,Ehsan, Shahana,Akbar, Wajiha,Faisal, Saniya
p. 742 - 748
(2018/07/15)

Synthesis, characterization, and in vitro evaluation of the selective P2Y2 receptor antagonist AR-C118925
The Gq protein-coupled, ATP- and UTP-activated P2Y2 receptor is a potential drug target for a range of different disorders, including tumor metastasis, inflammation, atherosclerosis, kidney disorders, and osteoporosis, but pharmacological studies are impeded by the limited availability of suitable antagonists. One of the most potent and selective antagonists is the thiouracil derivative AR-C118925. However, this compound was until recently not commercially available and little is known about its properties. We therefore developed an improved procedure for the synthesis of AR-C118925 and two derivatives to allow up-scaling and assessed their potency in calcium mobilization assays on the human and rat P2Y2 receptors recombinantly expressed in 1321N1 astrocytoma cells. The compound was further evaluated for inhibition of P2Y2 receptor-induced β-arrestin translocation. AR-C118925 behaved as a competitive antagonist with pA2 values of 37.2?nM (calcium assay) and 51.3?nM (β-arrestin assay). Selectivity was assessed vs. related receptors including P2X, P2Y, and adenosine receptor subtypes, as well as ectonucleotidases. AR-C118925 showed at least 50-fold selectivity against the other investigated targets, except for the P2X1 and P2X3 receptors which were blocked by AR-C118925 at concentrations of about 1?μM. AR-C118925 is soluble in buffer at pH 7.4 (124?μM) and was found to be metabolically highly stable in human and mouse liver microsomes. In Caco2 cell experiments, the compound displayed moderate permeability indicating that it may show limited peroral bioavailability. AR-C118925 appears to be a useful pharmacological tool for in vitro and in vivo studies.
Rafehi, Muhammad,Burbiel, Joachim C.,Attah, Isaac Y.,Abdelrahman, Aliaa,Müller, Christa E.
p. 89 - 103
(2017/03/11)

Synthesis and carbonic anhydrase inhibitory properties of novel uracil derivatives
Abstract Carbonic anhydrase (CA) inhibitors are valuable molecules based on several therapeutic applications, including antiglaucoma activity. In the present study, inhibition of two human cytosolic carbonic anhydrase isozymes I and II with some uracil derivatives (3-9) were investigated. Compounds 3-9 showed KI values in the range of 10.83-464 μM for hCA I and of 28.88-778.5 μM against hCA II, respectively. Kinetic investigations showed that similarly to classical CA inhibitors, all investigated natural compounds act as competitive inhibitors with 4-NPA as substrate. Uracil derivatives investigated here are promising agents which may be used as lead molecules in order to derivative novel carbonic anhydrase inhibitors that might be useful in medical applications.
Güney, Murat,?avdar, Hüseyin,?entürk, Murat,Ekinci, Deniz
p. 3261 - 3263
(2015/07/08)

Pyrimidine-fused heterocyclic frameworks based on an N4-arylcytosine scaffold: Synthesis, characterization, and PNA oligomerization of the fluorescent cytosine analogue 5,6-benzopC
A synthesis of an intrinsically fluorescent cytosine analogue 5,6-benzopC has been developed utilizing the reductive Ni-mediated cyclization of an N4-aryl,N4-(Boc)cytosine intermediate as a key step. 5,6-BenzopC was found to possess interesting fluorescence properties (φ = 0.79, EtOH; Stokes shift 113 nm). Peptide nucleic acid (PNA) oligomerization of the 5,6-benzopC monomer was carried out, followed by hybridization studies with complementary deoxyribonucleic acid (DNA) and ribonucleic acid (RNA) which showed the modification to be well tolerated in the sequence contexts examined. Initial attempts to synthesize the heterocyclic skeleton present in 5,6-benzopC resulted in the discovery of routes to the pyrimido[1,6-a]benzimidazole, pyrimido[1,6-a]quinazoline, and pyrimido[1,6-a]benzo[b]6-bora-1,3-diazine heterocyclic frameworks.
Suchy, Mojmír,Hudson, Robert H. E.
p. 3336 - 3347
(2014/05/06)

Sulfur analogs of pyrimidine bases: Synthesis of 2-alkylthio- and 4-alkylthio-5-bromouracils and in silico evaluation of their biological activity
The general reactivity of alkylthiouracils under bromination conditions has been examined. Twenty 2-alkylthio- and 4-alkylthio-5-bromouracils of potential biological activity have been prepared. The structures of these compounds were confirmed by elementa
Bartkowiak, Grazyna,Wyrzykiewicz, Elzbieta,Schroeder, Grzegorz
p. 1134 - 1139
(2013/10/21)

Novel acyclic amide-conjugated nucleosides and their analogues
An effective one-step synthesis of new amide-conjugated nucleosides and their analogues, in the presence of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4- methylmorpholinium chloride (DMT-MM) as the condensing agent, is presented. Substrate subunits carrying carboxylic group were obtained by acidic hydrolysis of Michael-type adducts of various 5-substituted uracil derivatives to methyl acrylate. Amine substrate was synthesized by reduction of 1-(2′- cyanoethyl)thymine with sodium borohydride in the presence of nickel (II) chloride as catalyst. Other applied amine substrates were 5′-amino- 5′-deoxythymidine and 5-aminouracil. Copyright Taylor & Francis Group, LLC.
Boncel, Slawomir,Walczak, Krzysztof
experimental part
p. 103 - 117
(2009/06/18)

Mild regioselective monobromination of activated aromatics and heteroaromatics with N-bromosuccinimide in tetrabutylammonium bromide
Highly regioselective nuclear bromination of activated aromatic and heteroaromatic compounds has been accomplished using N-bromosuccinimide in tetrabutylammonium bromide. Pre-dominant para-selective monobromination of activated aromatics such as phenols and anilines, rate acceleration of bromination for moderately activated and less reactive substrates on addition of acidic montmorillonite K-10 clay, with or without microwave assistance, are the notable features of this protocol.
Ganguly, Nemai C.,De, Prithwiraj,Dutta, Sanjoy
p. 1103 - 1108
(2007/10/03)

Pyrimidine phosphorylase as a target for imaging and therapy
Thymine analogs and methods for their use as diagnostic and therapeutic agents for tumors.
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Page/Page column 5

(2008/06/13)

Conversion of 2-deoxy-D-ribose into 2-amino-5-(2-deoxy-β-D-ribofuranosyl)pyridine, 2′-deoxypseudouridine, and other C-(2′-deoxyribonucleosides)
The synthesis of 2-amino-5-(2-deoxy-β-D-ribofuranosyl)pyridine 2a, 2-amino-5-(2-deoxy-α-D-ribofuranosyl)-pyridine 23, 2-amino-5-(2-deoxy-β-D-ribofuranosyl)-3-methylpyridine 2b, 2-amino-5-(2-deoxy-α-D-ribofuranosyl)-3-methylpyridine 29 and 5-(2-deoxy-β-D-ribofuranosyl)-2,4-dioxopyrimidine [2′-deoxypseudouridine] 30a is described. These C-nucleosides are prepared either from 2-deoxy-3,5-O-(1, 1, 3, 3-tetraisopropyldisiloxan-1,3-diyl)-D-ribofuranose 15 or from 2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-D-ribono-1,4-lactone 16, which are themselves prepared from 2-deoxy-D-ribose 13. The sugar derivatives are first allowed to react with the appropriate 5-lithio-pyridine or 5-lithio-pyrimidine derivatives, which are prepared from 5-bromo-2-(dibenzylamino)pyridine 12a, 5-bromo-2-[bis(4-methoxybenzyl)amino]pyridine 12b, 5-bromo-2-dibenzylamino-3-methylpyridine 25 and 5-bromo-2,4-bis(4-methoxybenzyloxy)pyrimidine 33. The products from the reactions between the lithio-derivatives and the lactol 15 are cyclized under Mitsunobu conditions; the products from the reactions between the lithio-derivatives and the lactone 16 are first reduced with L-Selectride before cyclization, also under Mitsunobu conditions, In all cases, the β-anomers of the protected C-nucleosides are the predominant products. Finally, the separation of the α- and β-anomers and the removal of all of the protecting groups are described.
Reese, Colin B.,Wu, Qinpei
p. 3160 - 3172
(2007/10/03)

Uracil reductase inactivators
The present invention relates to a group of 5-substituted uracil derivatives which are inactivators of uracil reductase and which are particularily useful in cancer chemotherapy, especially in combination with antimetabolite antineoplastic agents such as 5-fluorouracil (5-FU).
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(2008/06/13)

5-Fluorouracil derivatives
Novel compounds comprising 5-fluorouracil or 5-fluorouridine covalently linked to 5-ethynyluracil, 5-ethynyluridine or 5-propynyluracil and pharmaceutical compositions comprising such compounds are disclosed.
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(2008/06/13)

Pharmaceutical compositions of 5-substituted uracil compounds
Pharmaceutical compositions containing 5-substituted uracil compounds are disclosed. The compositions are preferably in the form of a tablet or capsule.
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(2008/06/13)

Synthesis of [2-14C,5-3H]cytosine and [2-14C,5-3H]uracil via bromination and catalytic bromine-tritium gas exchange
In micro-scale experiments, [2-14C,5-3H]cytosine and [2-14C,5-3H]uracil were synthesized via bromination and catalytic Br-3H exchange reaction with the use of [2-14C]cytosine and -uracil and tritium gas. The double labelling percentages of these products were 70 and 26, respectively. It was assumed that [2-14C,5-Br]uracil was subjected to reaction with hydrogen atom originally adsorbed on a palladium catalyst. This is to a lesser extent valid for [2-14C,5-Br]cytosine. The percentages of 3H labelling at 5 position of pyrimidine ring of cytosine and uracil were proved to be 96 and 73, respectively. For the analysis and purification of products, the HPLC eluting conditions using C18 reverse column and NaH2PO4 aqueous solution or H2O/methanol mixture as eluent were studied. Unreacted tritium gas was recovered with the use of adsorbents such as active charcoal and Zr-V-Fe getter.
Asano,Kiritani
p. 603 - 616
(2007/10/02)

Fluorine-free titanocenes and the use thereof
Fluorine-free titanocene compounds of the formula I or II STR1 in which both R1 radicals are preferably, independently of one another, cyclopentadienyl?, which is unsubstituted or substituted by alkyl,alkoxy or --Si(R2)3, and both R2 radicals are, in particular, alkyl, STR2 Z is --NR10 --, --0-- or --S--, Y is Cl, Br, I, CN, SCN, --O--CO--CH3, --O--CO--phenyl or --O--SO2 --CH3, n is 1 or 2, m is 0 or 1, where the sum of n and m must be 2, R3, R4 and R5 are in particular, independently of one another, hydrogen, Cl, alkyl, cycloalkyl, adamantyl, phenyl, pyrryl or biphenylyl, where these radicals are unsubstituted or substituted by alkyl, Cl, alkylthio, --NR8 R9, phenyl, phenylthio or C1 -C10 alkoxy, or R3, R4 and R5 are alkenyl, alkoxy, cycloalkoxy, phenoxy, benzyloxy, tetrahydrofurfuryloxy, alkylthio, cycloalkylthio, benzylthio or phenylthio, where R3 and R4 are not simultaneously hydrogen, and if Q is a pyrimidyl radical, at least one radical R3 or R4 is alkoxy, cycloalkoxy, phenoxy, benzyloxy, tetrahydrofurfuryloxy or alkenyloxy, and if Z is --NR10 --, R3 and R4 are Cl Br or I, both radicals R6, independently of one another, are alkyl or alkenyl or both radicals R6 together with the nitrogen atom to which they are bonded, form a morpholino radical, R7 is alkyl, cycloalkyl or phenyl, R8 is phenyl or α-tertiary C4 -C6 alkyl, R9 is, in particular, hydrogen, alkyl, cycloalkyl, phenyl or a STR3 radical, where, in addition, the two R9 radicals in --N(R9)2 are identical or different and, together with the nitrogen atom to which they are bonded, may form a 5- or 6-membered heterocyclic ring which, in addition to the nitrogen atom, may also contain further nitrogen, oxygen or sulfur atoms, R10 is as defined for R9 or additionally, in particular, is phenyl which is unsubstituted or substituted by Cl, C1 -C12 alkyl, C1 -C10 alkoxy, C1 -C8 alkylthio, phenylthio, morpholino or --N(C1 -C4 alkyl)2, X is --O--, --S--, STR4 methylene or ethylene, and A is C1 -C12 alkylene or --X--A--X-- is a direct bond, are suitable as photoinitiators for photopolymerisation of compounds containing ethylenically unsaturated double bonds.
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(2008/06/13)

4'-substituted nucleosides
Nucleosides compounds of Formula I: STR1 wherein B is a purine or a pyrimidine; X and X' are H; Y is H; Y' is OH, F or H; or Y' and X' together makes a bond; Z is STR2 where n is zero, one, two or three; or Y' and Z together form a cyclic phosphate ester; Z' is --CN, --CH3, CH2 N3 or --CH2 J, where J is a halogen atom; or Z' and Y' together are --CH2 O--; and pharmaceutically acceptable esters, ethers, amides, N-acyl moieties and salts thereof.
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(2008/06/13)

Photochemistry of Uracils in Halogenated Solvents
The photochemistry of uracil and 1-substituted and 1,3-disubstituted uracils in CHBr3-CH2Cl2 is investigated.Photolysis of uracil leads to the formation of 5,6-dibromo-5,6-dihydrouracil as the main product, with 5-bromouracil as the by-product.In contrast with this the 5-bromouracils are formed as the main products by the photolysis of 1-substituted and 1,3-disubstituted uracils, with the corresponding 5,6-dihydro- and 5-bromo-5,6-dihydrouracils as the by-products.The kinetics of the bromination reaction have also been investigated and based on these results a free radical mechanism is proposed.
Moltke-Leth, Claus,Joergensen, Karl Anker
p. 1487 - 1490
(2007/10/02)

In-cell Indirect Electrochemical Halogenation of Pyrimidine Bases and their Nucleosides to 5-Haloderivatives
Reaction of anodically generated "halonium" species (LiX or Bu4NX, LiClO4, MeCN, Pt/Pt; I2, LiClO4, MeCN) with pyrimidine bases and their nucleosides leads to 5-halo compounds in good yields.
Palmisano, G.,Danieli, B.,Santagostino, M.,Vodopivec, B.,Fiori, G.
p. 7779 - 7782
(2007/10/02)

Cerium(IV)-Mediated Halogenation at C-5 of Uracil Derivatives
Treatment of protected uracil nucleosides 1 or 2 with elemental iodine or metal halogenides and ceric ammonium nitrate (CAN) at 80 deg C gave the corresponding protected 5-halouracil nucleosides 3a-f in excellent yields.Treatment of the resulting crude 3a-f with 0.1 M NaOMe/MeOH at ambient temperature gave the corresponding 5-halouridines 4a-f in high overall yields from 1 or 2.Further, 5-halouraciles 9a-f were prepared in good yields by treatment of 1,3-dimethyluracil (7) or uracil (8) with elemental iodine, metal halogenides, or hydrochloric acid and CAN.Halouridines 4a-e also were obtained in good yields by treatment of unprotected uracil nucleosides 5 or 6 with halogen sources as above and CAN.
Asakura, Jun-ichi,Robins, Morris J.
p. 4928 - 4933
(2007/10/02)

NOVEL SYNTHESIS OF 5-HALOURACILS FROM 5-MERCURI-2,4-DIMETHOXYPYRIMIDINES
Direct C-mercuration of 2,4-dimethoxypyrimidine with mercury (II) acetate has been shown to give the 5-mercuri-derivative, which is readily converted, either directly or via 5,5'-mercuribis (2,4-dimethoxypyrimidine), into the 5-halo derivatives.Hydrolysis of the latter with hydrochloric acid affords the 5-halouracils.
Skul'ski, L.,Kuyava, A.,Vrochin'ski, P.
p. 205 - 208
(2007/10/02)

Chloroperoxidase Catalyzed Halogenation of Pyrimidine Bases
Treatment of uracil or cytosine with H2O2 and potassium halides in the presence of chloroperoxidase in potassium phosphate buffer solution at pH 3.0 resulted in halogenation of the substrates, whereas no reaction occured on thymine by a similar treatment.
Itahara, Toshio,Ide, Naoko
p. 2311 - 2312
(2007/10/02)

Nucleoside process
Process for producing 1-halo-2-deoxy-2-fluoroarabinofuranoside derivatives bearing protective ester groups from 1,3,5-tri-O-acylribofuranose; the 1-halo compounds are intermediates in the synthesis of therapeutically active nucleosidic compounds.
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(2008/06/13)

2,4,5 Trifluoro pyrimidine and process for preparing
A process for preparing 5-fluorouracil, and a novel starting compound for such process, are disclosed. The novel starting compound is 2,4,5-trifluoropyrimidine. The process comprises hydrolyzing the 2,4,5-trifluoropyrimidine at a temperature of about 2° to about 100° C., thereby directly producing the compound 5-fluorouracil. 5-fluorouracil is a known anti-tumor agent, which has been used in the treatment of various types of cancers. In addition, 5-fluorouracil is a starting material for the production of certain types of pro-drugs, which are metabolized to form 5-fluorouracil in the body, such as, for instance, the compound 1-(2-tetrahydrofuryl)-5-fluorouracil.
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(2008/06/13)

Studies on fluorinated pyrimidines. I. A new method of synthesizing 5-fluorouracil and its derivatives
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Miyashita,Matsumura,Shimadzu,Hashimoto
p. 3181 - 3190
(2007/10/02)

Mechanisms of Bromination of Uracil Derivatives. 5. Reaction of Uracil and 5-Bromouracil via Their Anions in Weakly Acidic Aqueous Solution
The rates of reaction of bromine with uracil, 1-methyluracil, 3-methyluracil, 1,3-dimethyluracil, 5-bromouracil, and 5-bromo-1,3-dimethyluracil have been measured in acidic, aqueous solutions (pH 0-5).For those derivatives having a methyl group at N1 the observed second-order rate constants are invariant with acidity, whereas for those derivatives having hydrogen at N1 they increase with decreasing acidity.These results suggest that reaction upon the anions of uracil, 3-methyluracil, and 5-bromouracil predominates at higher pH.The mechanistic implications of these findings are discussed.
Tee, Oswald S.,Berks, Charles G.
p. 830 - 835
(2007/10/02)

The addition of hydroxylamine to the halogenated uracils
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Priest,Scheffler,Sander
p. 29 - 32
(2007/10/02)

Analytical studies on thiouracils. II. Dissociation constants of thiouracils and their reactions with hydrogen peroxide (author's transl)
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Hatada,Mamori,Nakashima,Yoshimura
p. 668 - 672,669,670
(2007/10/04)