cas 4433-40-3, 5-Hydroxymethyluracil | Articles data

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Johnson,Litzinger
p. 1940
(1936)
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Phosphate-triggered self-assembly of N-[(uracil-5-yl)methyl]urea: A minimalistic urea-derived hydrogelator
N-[(Uracil-5-yl)methyl]urea is reported as a minimalistic low-molecular-weight hydrogelator (LMWHG). The unusual phosphate-induced assembly of this compound has been thoroughly investigated by IR, UV/Vis, and NMR spectroscopy, electron microscopy, and rheological experiments. This rare example of an anion-triggered urea-based LMWHG is the first example of a pyrimidine- and urea-containing molecule that can be forced into self-assembly in aqueous solution without additional aromatic or lipophilic groups. The gelator/phosphate ratio within the hydrogel was successfully determined by 31P MAS NMR spectroscopy. The hydrogel exhibits a very fast and repeatable self-healing property, and remarkable G' values. The viscoelastic properties of the hydrogel can easily be tuned by variation of the phosphate ratio. Minimalistic hydrogel: N-[(Uracil-5-yl)methyl]urea is reported as a minimalist low-molecular-weight hydrogelator (LMWHG), its assembly being induced by phosphate anions (see scheme). It is the first example of a pyrimidine- and urea-containing molecule that can be forced into self-assembly in aqueous solution without additional aromatic or lipophilic groups. The viscoelastic properties of the hydrogel can easily be tuned by variation of the phosphate ratio.
Kleinsmann, Alexander J.,Weckenmann, Nicole M.,Nachtsheim, Boris J.
p. 9753 - 9761
(2014)
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Bioorthogonal Chemical Signature Enabling Amplified Visualization of Cellular Oxidative Thymines
Cellular oxidative thymines, 5-hydroxymethyluracil (5hmU) and 5-formyluracil (5fU), are found in the genomes of a diverse range of organisms, the distribution of which profoundly influence biological processes and living systems. However, the distribution of cellular oxidative thymines has not been explored because of lacking both specific bioorthogonal labeling and sensitivity methods for single-cell analysis. Herein, we report a bioorthogonal chemical signature enabling amplified visualization of cellular oxidative thymines in single cells. The synthesized ATP-γ-alkyne, an ATP analogue with bioorthogonal tag modified on γ-phosphate can be specifically linked to cellular 5hmU by chemoenzymatic labeling. DNA with 5-alkynephosphomethyluracil were then clicked with azide (N3)-modified 5hmU-primer. Identification of 5fU is based on selective reduction from 5fU to 5hmU, subsequent chemoenzymatic labeling of the newly generated 5hmU, and cross-linking with N3-modified 5fU-primer via click chemistry. Then, all of the 5hmU and 5fU sites are encoded with respective circularized barcodes. These barcodes are simultaneously amplified for multiplexed single-molecule imaging. The above two kinds of barcodes can be simultaneously amplified for differentiated visualization of 5hmU and 5fU in single cells. We find these two kinds of cellular oxidative thymines are spatially organized in a cell-type-dependent style with cell-to-cell heterogeneity. We also investigate their multilevel subcellular information and explore their dynamic changes during cell cycles. Further, using DNA sequencing instead of fluorescence imaging, our proposed bioorthogonal chemical signature holds great potential to offer the sequence information of these oxidative thymines in cells and may provide a reliable chemical biology approach for studying the whole-genome oxidative thymines profiles and insights into their functional role and dynamics in biology.
Bai, Min,Cao, Xiaowen,Chen, Feng,Xue, Jing,Zhao, Yue,Zhao, Yongxi
p. 10495 - 10501
(2021)
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BICYCLIC KINASE INHIBITORS AND USES THEREOF
The invention relates to kinase inhibitors, in particular inhibitors of protein kinases including the SIK-family, CSF1R, HCK, TEK-family, BRK, ABL, KIT and/or their mutants. Although structurally similar to other bicyclic kinase inhibitors, the kinase inhibitors of the invention are distinctive; possessing a particular class of heterocyclic moiety. Such kinase inhibitors can display one or more certain properties distinct to their structurally similar kinase inhibitors. The kinase inhibitors of the invention or pharmaceutical compositions comprising them may be used in the treatment of a disorder or condition, such as a proliferative disorder, for example, a leukaemia or solid tumour. In particular, these and other structurally related kinase inhibitors may be used in the treatment of a proliferative disorder - such as a mixed phenotype acute leukaemia (MPAL) - characterised by (inter-alia) the presence of MEF2C protein, a human chromosomal translocation at 11q23, and/or a KMT2A fusion oncoprotein. The kinase inhibitors or pharmaceutical compositions of the invention may be used topically to modulate skin pigmentation in a subject, for example to impart UV protection and reduce skin cancer risk.
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Paragraph 613; 618

(2021/11/06)

FUSED PYRIMIDINE COMPOUNDS, COMPOSITIONS AND MEDICINAL APPLICATIONS THEREOF
The present disclosure relates to a class of fused pyrimidine compounds of Formula I, their stereoisomers, tautomers, pharmaceutically acceptable salts, polymorphs, solvates, and hydrates thereof. The present disclosure also relates to a process of preparation of these fused pyrimidine compounds, and to pharmaceutical compositions containing them.
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Paragraph 0308

(2021/04/02)

FGFR4 Inhibitor. Compositions and their use in pharmaceutical preparations
The invention provides 3 inhibitor which takes 4 - 4 dihydropyrimidine [5 - d,2] pyrimidine - (1H) FGFR4 ketone as a mother nucleus and has a covalent structure. The examples give 9 specific compounds and kinase inhibitory activity testing of these 9 compounds, wherein LX08 for FGFR4 kinase inhibitory activity is only 7 nm, lower than FIIN - 2 of the active control, and potential application prospects. In addition, by subjecting the synthesized compound to MALDI-TOF mass spectrometry, we found that compounds of LX01, LX05, LX06, LX07, LX08 are covalently bound to FGFR4 of Cys552, cannot covalently bind FGFR4 of Cys477, and LX09 are FGFR4 inhibitors which can be covalently bound to the two cysteines Cys552 and Cys477 in FGFR4.
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Paragraph 0057-0060

(2021/10/27)

Targeting the nucleotide salvage factor DNPH1 sensitizes BRCA-deficient cells to PARP inhibitors
Mutations in the BRCA1 or BRCA2 tumor suppressor genes predispose individuals to breast and ovarian cancer. In the clinic, these cancers are treated with inhibitors that target poly(ADP-ribose) polymerase (PARP). We show that inhibition of DNPH1, a protein that eliminates cytotoxic nucleotide 5-hydroxymethyl-deoxyuridine (hmdU) monophosphate, potentiates the sensitivity of BRCA-deficient cells to PARP inhibitors (PARPi). Synthetic lethality was mediated by the action of SMUG1 glycosylase on genomic hmdU, leading to PARP trapping, replication fork collapse, DNA break formation, and apoptosis. BRCA1-deficient cells that acquired resistance to PARPi were resensitized by treatment with hmdU and DNPH1 inhibition. Because genomic hmdU is a key determinant of PARPi sensitivity, targeting DNPH1 provides a promising strategy for the hypersensitization of BRCA-deficient cancers to PARPi therapy.
Fugger, Kasper,Bajrami, Ilirjana,Dos Santos, Mariana Silva,Young, Sarah Jane,Kunzelmann, Simone,Kelly, Geoff,Hewitt, Graeme,Patel, Harshil,Goldstone, Robert,Carell, Thomas,Boulton, Simon J.,MacRae, James,Taylor, Ian A.,West, Stephen C.
p. 156 - 165
(2021/05/03)

New Metal-Free Route towards Imidazole-Substituted Uridine
Nucleosides with a bi(hetero)aryl nucleobase have unique potential applications as antiviral drugs and molecular probes. The need for transition metal catalysis to synthesize these nucleosides from pre-functionalized building blocks and the use of nucleobase protection groups results in expensive and tedious syntheses. Herein we report that 5-imidazolyl-uracil can be obtained by scalable Van Leusen imidazole synthesis and regioselectively introduced on ribose to obtain the desired nucleoside in a 5 step synthesis (total yield 55 percent). The 5-imidazolyl moiety leads to improved fluorescence properties. The only side-product formed was characterized by 2D-NMR and X-ray crystallography and could be suppressed during synthesis in favor of the desired product.
Dehaen, Wim,Herdewijn, Piet,Mattelaer, Henri-Philippe,Van Hool, Anne-Sophie,Van Meervelt, Luc,Van der Auweraer, Mark,de Jong, Flip
supporting information

(2020/07/02)

ESI-CID spectral characterization and differentiation of the cross links of thymine formed by one electron oxidation with SO4 ●-
The analysis of urinary nucleosides is becoming a very good tool in the diagnosis of diseases like AIDS and cancer and consequently the identification of modified nucleosides using mass spectrometry is an area of utmost importance. In this context, there is a high relevance in the understanding of the mechanism of collisionally induced dissociation (CID) of these heterocyclics. The present work characterizes and differentiates the cross-linked products formed by one electron oxidation of thymine (T). Three dimers A, B and C, were analyzed, out of which the dimer A is a C5–C5’ cross link of two T molecules containing a fused tetrahydrofuran ring, while B and C are N–C cross linked products. B and C showed very similar fragmentation pattern but that of A was different. The differentiation between these three were made by monitoring two characteristic peaks, the water loss peak ([M+H]+) and the protonated T fragment ([T + H]+). The probable mechanism of formation of these fragments and their CID mechanism in both positive and negative ionization modes are also explained. The neutral losses of NH3, H2O and NHCO were the prominent mechanism in the positive mode, while in the negative mode, only NHCO and CO losses were observed.
Chandran, Jisha,Vishnu,Aravind, Usha K.,Aravindakumar
p. 53 - 60
(2019/06/18)

BICYCLIC UREA KINASE INHIBITORS AND USES THEREOF
The present disclosure provides compounds of Formula (I), (II), and (III). The provided compounds are able to bind protein kinases (e.g., SIK) and may be useful in modulating (e.g., inhibiting) the activity of a protein kinase (e.g., SIK, (e.g., SIK1, SIK2, or SIK3)) in a subject or cell. The provided compounds may be useful in treating or preventing a disease (e.g., proliferative disease, musculoskeletal disease, genetic disease, hematological disease, neurological disease, painful condition, psychiatric disorder, or metabolic disorder) in a subject in need thereof. Also provided are pharmaceutical compositions, kits, methods, and uses that include or involve a compound described herein.
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Paragraph 00260; 00261

(2018/09/25)

PYRIMIDINE DERIVATIVES AND THEIR USE IN TREATING OR PREVENTING A RESPIRATORY SYNCYTIAL VIRUS INFECTION
Pyrimidine derivatives of formula (I) wherein: Z is a direct bond or -(CH2)n- wherein n is 1 or 2; one of X and Y is N, CH or CF, and the other of X and Y is CH; one of R1 and R2 is selected from -NHR, -NR2, -OR, -SR, -S(O)R, -S(O)2R and a group of the following formula (A) and the other of R1 and R2 is selected from -NHR', -OH, -OR' and a group of the above formula (A); R is unsubstituted C1-C6 alkyl; R' is a group selected from C1-C6 alkyl, 5- to 12-membered aryl and C3-C6 cycloalkyl, which group is unsubstituted or substituted; W is -(CH2)m-, -CH2-O-CH2-, -CH2-S-CH2- or -CH2-S(O)2-CH2-; p is 1, q is an integer of 1 - 6 and V is N; or p is 1, q is 0 and V is CH; or p is 0, q is 0 and V is N; r is 0 or 1; and R3 is -(CH2)s-NH2 or -(CH2)s-OH wherein s is 0 or an integer of 1 to 4; and the pharmaceutically acceptable salts thereof are inhibitors of RSV and can therefore be used to treat or prevent an RSV infection.
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Page/Page column 23

(2018/03/28)

Oligonucleotide promoted peptide bond formation using a tRNA mimicking approach
TransferRNA's role in protein translation is the prime example of an Informational Leaving Group (ILG). A simplified model produced oligophenylalanine with a modified uracil as an ILG in the presence of specific oligonucleotides. Our preliminary studies contribute to the importance of hybrid species in bridging the gap between peptides and nucleic acids.
Mattelaer,Mattelaer,Papastavrou,Dehaen,Herdewijn
supporting information
p. 5013 - 5016
(2017/07/11)

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.
Nam, Jaehyuk,Jung, Yongseok,Jang, Woo-Dong
p. 11169 - 11172
(2017/10/17)

A process for preparing 5 - substituted benzyl - 2, 4 - diamino pyrimidine and its derivatives (by machine translation)
The invention discloses a process for preparing 5 - substituted benzyl - 2, 4 - diamino pyrimidine and derivatives thereof, in particular can be used for preparing omay pullin, b a oxygen animal pen amine pyrimidine, such as palestinian kuikui purin. The invention relates to 5 - hydroxymethyl uracil as raw materials, through the electrophilic substitution reaction, chlorinated, amino and hydrolysis step preparation 5 - substituted benzyl - 2, 4 - diamino pyrimidine and its derivatives. The method can be used for preparing various 5 - substituted benzyl - 2, 4 - diaminopyrimidines of the molecule, thereby avoiding the high-pressure reaction step, the safety is high, and is suitable for industrial production. (by machine translation)
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Paragraph 0047; 0062; 0066

(2018/01/11)

MK2 INHIBITORS AND USES THEREOF
The present invention provides compounds, compositions thereof, and methods of using the same.
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Paragraph 0321

(2016/04/09)

Synthesis of 5-hetaryluracil derivatives via 1,3-dipolar cycloaddition reaction
1,3-Dipolar cycloaddition is a convenient method for construction of various heterocyclic systems. We applied this method for the synthesis 5-hetaryluracil derivatives where substituted uracils played the role of 1,3-dipoles or dipolarophiles. Treatment of the nitrile oxide derived from 5-formyluracil and substituted alkenes gave the appropriate 5-(4,5-dihydroisoxazol-3-yl)pyrimidine-2,4(1H,3H)-diones, which by oxidation with N-bromosuccinimide were transformed into appropriate 5-(isoxazol-3-yl)uracils. When 5-cyanouracil was used as a dipolarophile in the reaction with nitrile oxides, generated from aromatic aldoximes, several 5-(1,2,4-oxadiazol-5-yl)uracils were obtained. An alternative reaction of 5-formyluracil with an excess of nitriles in the presence of cerium ammonium nitrate as an oxidant gave 1,2,4-oxadiazol-3-yl derivatives in moderate yields. (Chemical Equation Presented).
Jakubiec, Dominika,Przypis, ?ukasz,Suwiński, Jerzy W.,Walczak, Krzysztof Z.
p. 149 - 161
(2017/02/19)

2′-Deoxy-2′,2′-difluorothymidine analogues for radiolabeling with fluorine-18 and other biomedical applications
Novel 2′-deoxy-2′,2′-difluorothymidine analogues with potential applications as antiviral, cytotoxic and cancer imaging agents have been synthesized. Introduction of the hydroxymethyl functionality at the 5-position of 2′-deoxy-2′,2′-difluoruridine provided a key intermediate with a suitable synthetic handle for the generation of these nucleoside derivatives.
Doepner, Andreas M.,Aboagye, Eric O.,Barrett, Anthony G.M.
supporting information
p. 3293 - 3297
(2015/03/04)

Molecular basis for the substrate specificity and catalytic mechanism of thymine-7-hydroxylase in fungi
TET proteins play a vital role in active DNA demethylation in mammals and thus have important functions in many essential cellular processes. The chemistry for the conversion of 5mC to 5hmC, 5fC and 5caC catalysed by TET proteins is similar to that of T to 5hmU, 5fU and 5caU catalysed by thymine-7-hydroxylase (T7H) in the nucleotide anabolism in fungi. Here, we report the crystal structures and biochemical properties of Neurospora crassa T7H. T7H can bind the substrates only in the presence of cosubstrate, and binding of different substrates does not induce notable conformational changes. T7H exhibits comparable binding affinity for T and 5hmU, but 3-fold lower affinity for 5fU. Residues Phe292, Tyr217 and Arg190 play critical roles in substrate binding and catalysis, and the interactions of the C5 modification group of substrates with the cosubstrate and enzyme contribute to the slightly varied binding affinity and activity towards different substrates. After the catalysis, the products are released and new cosubstrate and substrate are reloaded to conduct the next oxidation reaction. Our data reveal the molecular basis for substrate specificity and catalytic mechanism of T7H and provide new insights into the molecular mechanism of substrate recognition and catalysis of TET proteins.
Li, Wenjing,Zhang, Tianlong,Ding, Jianping
p. 10026 - 10038
(2015/12/23)

Discovery of a bacterial 5-methylcytosine deaminase
5-Methylcytosine is found in all domains of life, but the bacterial cytosine deaminase from Escherichia coli (CodA) will not accept 5-methylcytosine as a substrate. Since significant amounts of 5-methylcytosine are produced in both prokaryotes and eukaryotes, this compound must eventually be catabolized and the fragments recycled by enzymes that have yet to be identified. We therefore initiated a comprehensive phylogenetic screen for enzymes that may be capable of deaminating 5-methylcytosine to thymine. From a systematic analysis of sequence homologues of CodA from thousands of bacterial species, we identified putative cytosine deaminases where a "discriminating" residue in the active site, corresponding to Asp-314 in CodA from E. coli, was no longer conserved. Representative examples from Klebsiella pneumoniae (locus tag: Kpn00632), Rhodobacter sphaeroides (locus tag: Rsp0341), and Corynebacterium glutamicum (locus tag: NCgl0075) were demonstrated to efficiently deaminate 5-methylcytosine to thymine with values of kcat/Km of 1.4 × 105, 2.9 × 104, and 1.1 × 103 M-1 s-1, respectively. These three enzymes also catalyze the deamination of 5-fluorocytosine to 5-fluorouracil with values of kcat/Km of 1.2 × 105, 6.8 × 104, and 2.0 × 102 M-1 s-1, respectively. The three-dimensional structure of Kpn00632 was determined by X-ray diffraction methods with 5-methylcytosine (PDB id: 4R85), 5-fluorocytosine (PDB id: 4R88), and phosphonocytosine (PDB id: 4R7W) bound in the active site. When thymine auxotrophs of E. coli express these enzymes, they are capable of growth in media lacking thymine when supplemented with 5-methylcytosine. Expression of these enzymes in E. coli is toxic in the presence of 5-fluorocytosine, due to the efficient transformation to 5-fluorouracil.
Hitchcock, Daniel S.,Fedorov, Alexander A.,Fedorov, Elena V.,Almo, Steven C.,Raushel, Frank M.
p. 7426 - 7435
(2015/04/16)

HETEROARYL COMPOUNDS AND USES THEREOF
The present invention relates to compounds useful as inhibitors of protein kinases, containing a cysteine residue in the ATP binding site. The invention further provides for pharmaceutically acceptable compositions comprising therapeutically effective amounts of one or more of the protein kinase inhibitor compounds and methods of using said compositions in the treatment of cancers and carcinomas.
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Paragraph 00353

(2014/09/29)

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.
Brognara, Eleonora,Lampronti, Ilaria,Breveglieri, Giulia,Accetta, Alessandro,Corradini, Roberto,Manicardi, Alex,Borgatti, Monica,Canella, Alessandro,Multineddu, Chiara,Marchelli, Rosangela,Gambari, Roberto
scheme or table
p. 30 - 37
(2012/05/04)

Hydrophilic modifications in peptide nucleic acid - Synthesis and properties of PNA possessing 5-hydroxymethyluracil and 5-hydroxymethylcytosine
We have investigated the chemistry for the incorporation of C5-hydroxymethyl-uracil and -cytosine in peptide nucleic acid (PNA) and the subsequent effect of this modification on PNA hybridization behavior. Largely based on literature precedent, we prepared a peptide nucleic acid monomer, possessing 5-hydroxymethyuracil, which was compatible with Fmoc-based oligopeptide synthesis. An improved, large-scale synthesis of 5-hydroxymethylcytosine was developed, as a starting point for the synthesis of a monomer containing this nucleobase. In each case, the hydroxyl group was blocked as a t-butyldiphenylsilyl ether, and the exocyclic amino group of cytosine was additionally blocked with the benzoyl-group. The modified monomers were incorporated into isolated positions in the oligomer sequence using standard protocols. The modified oligomers showed that the 5-hydroxymethyl group is compatible with triplex and duplex formation.
Hudson, Robert H. E.,Liu, Yuhong,Wojciechowski, Filip
p. 302 - 312
(2008/09/18)

The detrimental effect of orotic acid substitution in the peptide nucleic acid strand on the stability of PNA2:NA triple helices
We have investigated the incorporation of C6 derivatives of uracil into polypyrimidine peptide nucleic acid oligomers. Starting with uracil-6-carboxylic acid (orotic acid), a peptide nucleic acid monomer compatible with Fmoc-based synthesis was prepared. This monomer then served as a convertible nucleobase whereupon treatment of the resin-bound methyl orotate containing hexamers with hydroxide or amines cleanly converted the ester to an orotic acid or orotamide-containing peptide nucleic acid. Peptide nucleic acid hexamers containing the C6-modified nucleobase hybridized to both poly(riboadenylic acid) and poly(deoxyriboadenylic acid) via triplex formation. Complexes formed with poly(riboadenylic acid) were more stable than those formed with poly(dexoyriboadenylic acid), as measured by temperature-dependent UV spectroscopy. However, both of these complexes were destabilized relative to the complexes formed by an unmodified peptide nucleic acid oligomers. Internal or doubly substituted hexamers are destabilized more strongly than a terminally substituted one, and the type of substitution (carboxamide, ester, carboxylic acid) affects the overall triplex stability. These results clearly show that incorporation of a C6-substituted uracil into polypyrimidine PNA is detrimental to triplex formation. We have also extended this chemistry to incorporate uracil-5-methylcarboxylate into a peptide nucleic acid hexamer. After on-resin conversion of the C5 ester to the 3-(N,N-dimethylamino)propylamide, significant stabilization of the triplex formed with poly(riboadenylic acid) was observed, which illustrates the compatibility of C5 substitution with peptide nucleic acid directed triple helix formation.
Hudson, Robert H. E.,Wojciechowski, Filip
p. 1731 - 1740
(2007/10/03)

PYRIMIDO COMPOUNDS HAVING ANTIPROLIFERATIVE ACTIVITY
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Page/Page column 4-6

(2008/06/13)

Novel dihydropyridinone compounds
Disclosed are novel dihydropridinone compounds that are selective inhibitors of both KDR and FGFR kinases. These compounds and their pharmaceutically acceptable salts are anti-proliferative agents useful in the treatment or control of solid tumors, in particular breast, colon lung and prostate tumors. Also, disclosed are pharmaceutical compositions containing these compounds and methods of treating cancer.
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Page/Page column 10

(2010/02/07)

Pyrimido compounds having antiproliferative activity
Disclosed are novel pyrimido compounds that are selective inhibitors of both KDR and FGFR kinases. These compounds and their pharmaceutically acceptable salts are anti-proliferative agents useful in the treatment or control of solid tumors, in particular breast, colon, lung and prostate tumors. Also disclosed are pharmaceutical compositions containing these compounds and methods of treating cancer.
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Page/Page column 6; 9

(2010/02/08)

Mild generation of 5-(2′-deoxyuridinyl)methyl radical from a phenyl selenide precursor
(Chemical Equation Presented) 5-(2′-Deoxyuridinyl)methyl radical (1) resulting from formal hydrogen atom abstraction from the methyl group of thymidine is produced from the respective phenyl selenide precursor (2) via 350 nm photolysis or mild thermolysis (37°C in the presence of glutathione) under aerobic or anaerobic conditions. The mild thermal generation of a nucleoside radical provides an alternative to previously reported photochemical methods, which are not always compatible with nucleic acids.
In, Seok Hong,Greenberg, Marc M.
p. 5011 - 5013
(2007/10/03)

Isoxazolidine analogues of pseudouridine: A new class of modified nucleosides
A new class of modified C-nucleosides has been synthesized according to the 1,3-dipolar cycloaddition methodology. The obtained compounds are structurally related to natural pseudouridine, where the sugar moiety is replaced by an isoxazolidine ring. Different experimental conditions, and the effect of additives on the cycloaddition process, have been examined; the best results were obtained when the cycloaddition reaction was performed under microwave irradiation.
Chiacchio, Ugo,Corsaro, Antonino,Mates, Juan,Merino, Pedro,Piperno, Anna,Rescifina, Antonio,Romeo, Giovanni,Romeo, Roberto,Tejero, Tomas
p. 4733 - 4738
(2007/10/03)

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.
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Page 14; 17

(2010/02/06)

Efficient synthesis of 5-hydroxymethyl pyrimidines and their nucleosides using microwave irradiation
Hydroxymethylation of uracil (1), cytosine (3), 5-hydroxymethyl-2′,3′-O-isopropylideneuridine (5), 5′-O-tert-butyldiphenylsilyl-2′,3′-O-isopropylideneuridine (7), 2′,3′-O-isopropylidenecytidine (9) and 2′,3′-O-isopropylidene-5′-O-tritylcytidine (11) was efficiently carried out with paraformaldehyde in alkaline medium under microwave irradiation in very high yield.
Abdel-Rahman, Adel A.-H.,El Ashry, El Sayed H.
p. 2043 - 2044
(2007/10/03)

PYRIMIDINEDIONE, PYRIMIDINETRIONE, TRIAZINEDIONE AND TETRAHYDROQUINAZOLINEDIONE DERIVATIVES AS ALPHA1-ADRENERGIC RECEPTOR ANTAGONISTS
Compounds of Formula I: STR1 where R 5 is a group selected from Formulae (a), (b), (c) and (d): STR2 and the pharmaceutically acceptable salts and N-oxides thereof, are α 1-adrenergic receptor antagonists useful for the treatment of diseases involving directly or indirectly an obstruction of the lower urinary tract, such as benign prostatic hyperplasia.
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(2008/06/13)

Hydroxyl radical-induced cross-linking of thymine and lysine: Identification of the primary structure and mechanism
Hydroxyl radical-induced formation of a cross-link of thymine (Thy) and lysine (Lys) in the γ-radiolysis of N2O-saturated aqueous solution was studied. A Thy-Lys cross-link (I) of the formal structure that OH radical and 4-carbon-centered Lys radical added respectively to C(5) and C(6) positions of Thy was isolated by a preparative HPLC and identified by a FAB-HRMS. The primary cross-link I was dehydrated by treatment with HCl at 120°C to yield the secondary structure (II) possessing a C(5)-C(6) double bond in the Thy moiety: the latter structure II was reported previously (Dizdaroglu, M.; Gajewski, E. Cancer Res. 1989, 49, 3463-3467). A pulse radiolysis study with a redox titration method indicated that 4-carbon centered Lys radical intermediate was of neutral redox reactivity in contrast to reducing reactivity of 5-hydroxy-5,6-dihydrothymin-6-yl radical intermediate. The cross-link I could be formed by a conventional radical recombination mechanism, but not by an ionic recombination mechanism involving a redox reaction between the radical intermediates.
Morimoto, Syota,Hatta, Hiroshi,Fujita, Shin-Ichi,Matsuyama, Tomochika,Ueno, Toru,Nishimoto, Sei-Ichi
p. 865 - 870
(2007/10/03)

Preparation and reactions of zincated thymine derivatives
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Berillon,Wagner,Knochel
p. 9117 - 9121
(2007/10/03)

Pyrimidinedione, pyrimidinetrione, triazinedione, tetrahydroquinazolinedione derivatives as alpha-1-adrenergic receptor antagonists
The present invention relates to novel α1-adrenoceptor antagonists of the formula I*(formula 01)* in which: R1 is acetylamino, amino, cyano, trifluoroacetylamino, halo, hydro, hydroxy, nitro, methylsulfonylamino, 2-propynyloxy, a group selected from (C1-6)alkyl, (C3-6)cycloalkyl, (C3-6)cycloalkyl(C1-4)alkyl, (C1-6)alkyloxy, (C3-6)cycloalkyloxy, (C3-6)cycloalkyl(C1-4)alkyloxy and (C1-4)alkylthio (which group is optionally further substituted with one to three halo atoms) or a group selected from aryl, aryl(C1-4)alkyl, heteroaryl, heteroaryl(C1-4)alkyl, aryloxy, aryl(C1-4)alkyloxy, heteroaryloxy and heteroaryl(C1-4)alkyloxy (which aryl and heteroaryl are optionally further substituted with one to two radicals independently selected from halo and cyano); R2 is cyano, halo, hydro, hydroxy or a group selected from (C1-6)alkyl and (C1-6)alkyloxy (which group is optionally further substituted with one to three halogen atoms);R3 and R4 are both hydro or methyl or together are ethylene; and R5 is a group selected from Formulae (a), (b), (c) and (d):*(formula 02)* in which: X is C(O), CH2 or CH(OH); Y is CH2 or CH(OH); Z is N or C(R9), wherein R9 is hydro, (C1-6)alkyl or hydroxy; R6 is hydro, a group selected from (C1-6)alkyl, (C3-6)cycloalkyl, (C3-6)cycloalkyl(C1-4)alkyl (which group is optionally further substituted with one to three halo atoms) or a group selected from aryl, heteroaryl, aryl(C1-4)alkyl and heteroaryl(C1-4)alkyl (which aryl and heteroaryl are optionally further substituted with one to three radicals selected from halo, cyano, (C1-6)alkyloxy, (C1-6)alkyl and aryl); R7 is (C1-6)alkanoyl, carbamoyl, cyano, di(C1-6)alkylamino, halo, hydro, hydroxy, hydroxyiminomethyl, (C1-6)alkylsulfonyl, (C1-6)alkylthio, a group selected from (C1-6)alkyl, (C3-6)cycloalkyl,(C1-6)alkyloxy and (C1-6)alkyloxy(C1-4)alkyl (which group is optionally further substituted with one to three radicals selected from halo, hydroxy or (C1-6)alkyloxy) or a group selected from aryl, heteroaryl, aryl(C1-4)alkyl and heteroaryl(C1-4)alkyl (which aryl and heteroaryl are optionally further substituted with one to three radicals selected from halo, cyano, (C1-6)alkyloxy, (C1-6)alkyl and aryl) or R7 and R9 together are tetramethylene; and each R8 is independently hydro, hydroxy, methyl or ethyl; and the pharmaceutically acceptable salts and N-oxides thereof.
-
(2008/06/13)

Measurement of oxidative damage at pyrimidine bases in γ-irradiated DNA
Oxidized nucleobases represent one of the main classes of damage induced in DNA by ionizing radiation. Emphasis was placed in this work on the measurement of four oxidized pyrimidine bases, including 5- (hydroxymethyl)uracil (5-HMUra), 5-formyluracil (5-ForUra), 5-hydroxy- cytosine (5-OHCyt), and 5-hydroxyuracil (5-OHUra), in isolated DNA upon exposure to γ radiation in aerated aqueous solution. For this purpose, both high performance liquid chromatography associated with electrochemical detection (HPLC-EC) and gas chromatography coupled to mass spectrometry (GC- MS) were used. Conditions of hydrolysis of the N-glycosidic bond were carefully checked in order to achieve a quantitative release of the lesions. We showed that 60% formic acid treatment leads to the decomposition of the four lesions studied. On the other hand, hydrolysis based on the use of either 88% formic acid or 70% hydrogen fluoride in pyridine (HF/Pyr) allowed the quantitative release of the modified bases, with the exception of 5- HMUra when the latter reagent was utilized. A dose course study of the radiation-induced formation of 5-HMUra and 5-ForUra in DNA by using the GC- MS assay showed that the latter lesion was produced in a 2.1-fold higher yield than the former one. HF/Pyr and 88% formic acid hydrolysis provided similar results for 5-ForUra, indicating the reliability of both techniques for the measurement of this lesion. For 5-OHUra and 5-OHCyt, the level of modification determined by GC-MS analysis was higher after 88% formic acid treatment than upon HF/Pyr hydrolysis. When DNA was enzymatically digested and analyzed by HPLC-EC for 5-OHdCyd and 5-OHdUrd, the results were very close to those obtained by GC-MS following HF/Pyr treatment. It was concluded that additional amounts of both 5-OHUra and 5-OHCyt are produced during the 88% formic acid treatment from radiation-induced 5,6-saturated pyrimidine precursors. It is likely that cytosine and uracil diols are involved in this reaction. The radiochemical yields of formation (in μmol · J-1) for the products studied are in the following decreasing order: 5-ForUra (0.0083) > 5-OHCyt (0.0046) > 5-HMUra (0.0039) > 5-OHUra (0.0035).
Douki, Thierry,Delatour, Thierry,Paganon, Frederique,Cadet, Jean
p. 1145 - 1151
(2007/10/03)

Oxidation of nucleic acid related compounds by the peroxodisulfate ion
The treatment of nucleic acid bases, nucleosides, and nucleotides with peroxodisulfate ion in a phosphate buffer solution at pH 7.0 or water at 70-75°C was investigated. The reaction of thymine and 5-methylcytosine nucleosides and nucleotides resulted in the oxidation of the 5-methyl groups. The oxidation products from 1,3-dimethyluracils and the time-course of the reaction of uracils led to two plausible reaction mechanisms for the oxidation of uracils.
Itahara,Yoshitake,Koga,Nishino
p. 2257 - 2264
(2007/10/02)

Reactions of cobalt(III) complexes with free radicals derived from thymine
The nature of interaction of Co(III) complexes such as Co(III)EDTA and Co(III)NTA with transient adducts of thymine such as TOH·, T·-, and TH· formed in the gamma radiolysis of thymine were studied. The study shows that TOH radicals do not undergo electron transfer reaction with Co(III) complexes whence no radiosensitization of thymine by Co(III) complexes was observed. Electron transfer however, takes place from T·- and TH· to Co(III) complexes. A plausible mechanism of radiolysis of thymine in presence of Co(III) complexes is discussed.
Chakrabarti,Mandal,Bhattacharyya
p. 693 - 703
(2007/10/03)

Reactions of Ni(II) and its complexes with free radicals derived from thymine
The effects of nickel(II) ions and its complexes on the products arising from the γ-radiolysis of thymine were studied.The decomposition of the pyrimidine base and formation of different radiolytic products indicate that nickel(II) ions or its complexes have little effect on the radiosensitivity of thymine.The transient hydroxyl adduct of thymine reacts with Ni(II) with the formation of a complex having a nickel-carbon bond.The rate constants for the reactions are of the order of 106 dm3mol-1s-1.Possible mechanisms for the formation of different products in the radiolysis of thymine in the presence of nickel(II) compounds are discussed.
Chakrabarti, S.,Mandal, P. C.,Bhattacharyya, S. N.
p. 307 - 312
(2007/10/02)

1-(5'-Fluoro-6'-hydroxy-5',6'-dihydrouracil-5'-yl)-5-fluorouracil, a novel N(1)-C(5)-linked dimer that releases 5-fluorouracil by radiation activation under hypoxic conditions [1]
-
Nishimoto,Hatta,Ueshima,Kagiya
p. 2711 - 2712
(2007/10/02)

Effect of Fe(III) ions on the γ-radiolysis of thymine
-
Bhattacharyya,Mandal,Chakrabarti
p. 3001 - 3005
(2007/10/02)

Oxidation of Thymines by Peroxosulfate Ions in Water
Oxidation of thymines by sodium peroxodisulfate in water at 85 deg C gave the corresponding 5-(hydroxymethyl)uracils and 5-formyluracils.The reaction may proceed via thymine cation radicals.On the other hand, oxidation of thymines by potassium peroxomonosulfate in water gave the corresponding cis-5,6-dihydroxy-5,6-dihydrothymines and 5-hydroxy-5-methylbarbituric acids.Furthermore, treatment of thymine with both potassium peroxomonosulfate and hydrogen peroxide in water gave cis-6-hydroperoxy-5-hydroxy-5,6-dihydrothymine.
Itahara, Toshio,Fujii, Yukiko,Tada, Miki
p. 3421 - 3424
(2007/10/02)

Far ultraviolet induced decomposition of thymine in deaerated and aerated aqueous solutions
Thymine in aqueous solution was decomposed with quantum yields of 0.3 and 0.4 under N2-saturated and aerated conditions by far-ultraviolet light (>180 nm, far-uv), and quantum yields of 2E-4 and 3E-4 by near-ultraviolet light (>220 nm, near-uv), respectively.The main photolytic products by far-uv were 5,6-dihydrothymine (DHT) (selectivity: S(DHT) = 0.2) and 5-hydroxymethyluracil (HMU) (S(HMU) = 0.1) under N2-saturated conditions. cis- and trans-5,6-Dihydroxy-5,6-dihydrothymine (TG), 6(5)-hydroperoxy-5(6)-hydroxy-5,6-dihydrothymine (HTP) (S(TG) + S(HTP) = 0.2), and N1-formyl-N2-pyruvylurea (FPU) (S(FPU) = 0.4) were obtained under aerated conditions.These products were attributed to the reactions of thymine with the radical H and radical O produced by photolysis of water.
Ohtani, Bunsho,Nagasaki, Hiroshi,Nishimoto, Sei-ichi,Sakano, Koichi,Kagiya, Tsutomu
p. 2297 - 2300
(2007/10/02)

Oxidation of Thymines and Uracils with Sodium Peroxodisulfate
Reaction of thymines with Na2S2O8 in water resulted in selective oxidation of the methyl group at 5-position of thymines.Oxidation of thymines with Na2S2O8 in hydrochloric acid gave 5-chloro-6-hydroxy-5,6-dihydrothymines and in acetic acid containing NaCl gave 6-acetoxy-5-chloro-5,6-dihydrothymines which were converted to 6-alkoxy-5-chloro-5,6-dihydrothymines with alcohols.The reaction of uracils also gave similar products together with 5-chlorouracils.
Itahara, Toshio,Ebihara, Reiko,Fujii, Yukiko,Tada, Miki
p. 1319 - 1322
(2007/10/02)

Elimination Reactions of α-Substituted Thymines Derived from Tautomeric Heterocyclic Thiols and Selenols
Tautomeric heterocyclic thiols are readily alkylated by 5-(halomethyl)uracils, giving both S- and N-substituted products.S derivatives such as 19 undergo rapid elimination of thiolate anion in base, whereas the isomeric 6-substituted uracil drivatives such as 3 show no elimination.Kinetic and 13C NMR studies are consistent with an elimination mechanism involving heterocyclic quinone methide intermediate, which can arise from the 5-substituted uracil derivatives but not from the 6-substituted series.The proposed mechanism is further supported by studies of the pH dependency of the elimination reaction and of the effect of substitution in the uracil ring (see Table I and Scheme II).N-Substituted (thione) derivatives such as 36 also undergo base-catalyzed elimination, but a rates some 105 to 106 times slower than those for the corresponding S derivatives when the uracil is unsubstituted on nitrogen.The high sensivity of elimination rate to changes in the leaving group atom is attributed to a transition state in which the connecting methylene group has considerable carbocation character (see Scheme VI).Analogous derivatives (such as 42) of tautomeric heterocyclic selenols have also been prepared, and their elimination kinetics further support this interpretation.
Bartles-Keith, James R.,Mahoney, J. Barry,Puttick, Anthony J.
p. 980 - 987
(2007/10/02)

Acyclopyrimidine C-nucleosides. Synthesis of acyclopseudoisocytidine and its derivatives
-
Chu
p. 9 - 11
(2007/10/02)

PROMOTION EFFECT OF 2,2,6,6-TETRAMETHYLPIPERIDINE-1-OXYLS ON THE RADIOLYTIC HYDROXYLATION OF THYMINE IN DEAERATED AQUEOUS SOLUTION
Remarkable promotion of the hydroxylation of thymine to give thymine glycol with almost complete depression of side reactions by 2,2,6,6-tetramethylpiperidine-1-oxyl (TMPO.) derivatives was observed in the γ-radiolyses of the N2- and N2O-saturated aqueous solutions.In the O2-saturated solution, TMPO. depressed the thymine conversion close to the level under N2 while promoted the formation of thymine glycol to some extent by decreasing side reactions.
Kagiya, Tsutomu,Kimura, Ryoji,Komuro, Chikara,Sakano, Koichi,Nishimoto, Sei-ichi
p. 1471 - 1474
(2007/10/02)

RADIATION-INDUCED HYDROXYLATION OF THYMINE SENSITIZED BY NITRO COMPOUNDS IN N2O-SATURATED AQUEOUS SOLUTION
Hydroxylation of thymine (1) to give thymine glycol (3) is remarkably promoted by the addition of nitro compounds (2a-f) in the γ-radiolysis of the N2O-saturated aqueous solution, although overall decomposition of 1 is depressed to some extent.The G-value of 3 increases linearly with increasing the one-electron reduction potential of 2a-f.
Wada, Takeshi,Ide, Hiroshi,Nishimoto, Sei-ichi,Kagiya, Tsutomu
p. 1041 - 1044
(2007/10/02)

The strucutre of polyoxin C.
-
Isono,Suzuki
p. 203 - 208
(2007/10/08)

Hydroxymethylation of pyrimidine mononucleotides with formaldehyde.
-
Alegria
p. 317 - 324
(2007/10/04)

Preparation and properties of 2,6-dichloro-5-chloromethylpyrimidine
-
Brossmer,R?hm
p. 119 - 133
(2007/10/06)

Chemical Properties

Appearance/Colour :White Powder
Melting Point: >300 °C
Boiling Point: 530.4 °C at 760 mmHg
Flash Point:274.6 °C
Density: 1.401 g/cm³
Solubility:DMSO (Slightly, Heated), Methanol (Slightly, Heated), Water (Slightly, Heated)
Storage Temp.:Refrigerator
Vapor Pressure: 4.44E-12mmHg at 25°C
Refractive Index: 1.528
PKA: 8.46±0.10(Predicted)
BRN: 125482
PSA: 86.47000
LogP: -0.61990

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4433-40-3

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Chemical Properties

Appearance/Colour :White Powder

Melting Point: >300 °C

Boiling Point: 530.4 °C at 760 mmHg

Flash Point:274.6 °C

Density: 1.401 g/cm³

Solubility:DMSO (Slightly, Heated), Methanol (Slightly, Heated), Water (Slightly, Heated)

Storage Temp.:Refrigerator

Vapor Pressure: 4.44E-12mmHg at 25°C

Refractive Index: 1.528

PKA: 8.46±0.10(Predicted)

BRN: 125482

PSA: 86.47000

LogP: -0.61990

Global suppliers and manufacturers of 4433-40-3total 107 suppliers on LookChem

Article Database

4433-40-3

Articles about 4433-40-3Total 49 be found

More Articles about upstream products of 4433-40-3

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Chemical Properties

Appearance/Colour :White Powder

Melting Point: >300 °C

Boiling Point: 530.4 °C at 760 mmHg

Flash Point:274.6 °C

Density: 1.401 g/cm3

Solubility:DMSO (Slightly, Heated), Methanol (Slightly, Heated), Water (Slightly, Heated)

Storage Temp.:Refrigerator

Vapor Pressure: 4.44E-12mmHg at 25°C

Refractive Index: 1.528

PKA: 8.46±0.10(Predicted)

BRN: 125482

PSA: 86.47000

LogP: -0.61990

Global suppliers and manufacturers of 4433-40-3total 107 suppliers on LookChem

Density: 1.401 g/cm³