Pyrimidines

Soares de Melo, Candice’s team published research in Journal of Medicinal Chemistry in 2021 | CAS: 3764-01-0

2,4,6-Trichloropyrimidine(cas: 3764-01-0) is a member of organic chlorides. Organic chlorides are compounds containing a carbon-chlorine bond, which are widely used in the oil field as a wax dissolver. They are generally not present in crude oils and are typically the result of additives, cleaning solutions or chemicals used for oil recovery.Related Products of 3764-01-0

Related Products of 3764-01-0In 2021 ,《Antitubercular 2-Pyrazolylpyrimidinones: Structure-Activity Relationship and Mode-of-Action Studies》 appeared in Journal of Medicinal Chemistry. The author of the article were Soares de Melo, Candice; Singh, Vinayak; Myrick, Alissa; Simelane, Sandile B.; Taylor, Dale; Brunschwig, Christel; Lawrence, Nina; Schnappinger, Dirk; Engelhart, Curtis A.; Kumar, Anuradha; Parish, Tanya; Su, Qin; Myers, Timothy G.; Boshoff, Helena I. M.; Barry, Clifton E. III; Sirgel, Frederick A.; van Helden, Paul D.; Buchanan, Kirsteen I.; Bayliss, Tracy; Green, Simon R.; Ray, Peter C.; Wyatt, Paul G.; Basarab, Gregory S.; Eyermann, Charles J.; Chibale, Kelly; Ghorpade, Sandeep R.. The article conveys some information:

Phenotypic screening of a Medicines for Malaria Venture compound library against Mycobacterium tuberculosis (Mtb) identified a cluster of pan-active 2-pyrazolylpyrimidinones. The biol. triage of these actives using various tool strains of Mtb suggested a novel mechanism of action. The compounds were bactericidal against replicating Mtb and retained potency against clin. isolates of Mtb. Although selected MmpL3 mutant strains of Mtb showed resistance to these compounds, there was no shift in the min. inhibitory concentration (MIC) against a mmpL3 hypomorph, suggesting mutations in MmpL3 as a possible resistance mechanism for the compounds but not necessarily as the target. RNA transcriptional profiling and the checkerboard board 2D-MIC assay in the presence of varying concentrations of ferrous salt indicated perturbation of the Fe-homeostasis by the compounds Structure-activity relationship studies identified potent compounds with good physicochem. properties and in vitro microsomal metabolic stability with moderate selectivity over cytotoxicity against mammalian cell lines. After reading the article, we found that the author used 2,4,6-Trichloropyrimidine(cas: 3764-01-0Related Products of 3764-01-0)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Wang, Ruifeng’s team published research in European Journal of Medicinal Chemistry in 2019 | CAS: 90213-66-4

2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine(cas: 90213-66-4) belongs to pyrimidine. The pyrimidine ring system has wide occurrence in nature as substituted and ring fused compounds and derivatives, including the nucleotides cytosine, thymine and uracil, thiamine (vitamin B1) and alloxan. Quality Control of 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

Quality Control of 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidineIn 2019 ,《Design, synthesis and biological evaluation of novel 7H-pyrrolo[2,3-d]pyrimidine derivatives as potential FAK inhibitors and anticancer agents》 appeared in European Journal of Medicinal Chemistry. The author of the article were Wang, Ruifeng; Chen, Yixuan; Zhao, Xiangxin; Yu, Sijia; Yang, Bowen; Wu, Tianxiao; Guo, Jing; Hao, Chenzhou; Zhao, Dongmei; Cheng, Maosheng. The article conveys some information:

A series of 7H-pyrrolo[2,3-d]pyrimidine derivatives possessing a dimethylphosphine oxide moiety I (20a-i, R5, R6, R7 = H, R3 = acylamino, sulfamoyl, phosphonomethyl, carbamoyl, amino; 25a-h, R3 = 4-piperidinylaminocarbonyl, R5 = H, halo, alkoxy, CF3, R6 = H, Me, F, R7 = H, F) and II (22a-g, R4 = Me. CHF2CH2, MeOCH2CH2, tetrahydropyranyl, piperidinyl, CH2CONMe2) were designed, synthesized and evaluated as novel Focal adhesion kinase (FAK) inhibitors. Most compounds potently suppressed the enzymic activities of FAK, with IC50 values in the 10-8-10-9 M range, and potently inhibited the proliferation of breast (MDA-MB-231) and lung (A549) cancer cell lines. The representative compound 25b (R5 = OMe, R6 = R7 = H) exhibited potent enzyme inhibition (IC50 = 5.4 nM) and good selectivity when tested on a panel of 26 kinases. Compound 25b exhibited antiproliferative activity against A549 cells (IC50 = 3.2 μM) and relatively less cytotoxicity to a normal human cell line HK2. Compound 25b also induced apoptosis and suppressed the migration of A549 cells in a concentration-dependent manner. Further profiling of compound 25b revealed it had good metabolic stability in mouse, rat and human liver microsomes in vitro and showed weak inhibitory activity against various subtypes of human cytochrome P 450. The docking study of compound 25b was performed to elucidate its possible binding modes and to provide a structural basis for further structure-guided design of FAK inhibitors. In the experimental materials used by the author, we found 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine(cas: 90213-66-4Quality Control of 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Solberg, Jan’s team published research in Acta Chemica Scandinavica in 1989-01-31 | 99469-85-9

Acta Chemica Scandinavica published new progress about Coupling reaction. 99469-85-9 belongs to class pyrimidines, and the molecular formula is C5H4Cl2N2S, Recommanded Product: 4,5-Dichloro-2-(methylthio)pyrimidine.

Solberg, Jan; Undheim, Kjell published the artcile< Regiochemistry in palladium-catalyzed organotin reactions with halopyrimidines>, Recommanded Product: 4,5-Dichloro-2-(methylthio)pyrimidine, the main research area is halopyrimidine coupling organotin palladium catalyzed; regiochem halopyrimidine coupling organotin.

Chlorines in activated pyrimidine position are replaced by carbon substituents in Pd-catalyzed reactions with organotin compounds The 4(6)-position is more reactive than the 2-position allowing for regioselective coupling in 2,4(6)-dihalopyrimidines. A bromine substituent is required for coupling in the benzenoid 5-position. In 5-bromo-2,4-dichloropyrimidine the 4-chlorine is replaced before the 5-bromine and the latter before the 2-chlorine substituent, all in a regioselective manner. The methodol. can be used to introduce functionalized carbon substituents into any pyrimidine position.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Elston, C’s team published research in International Journal for Radiation Physics and Chemistry in 1971 | 2244-11-3

International Journal for Radiation Physics and Chemistry published new progress about ESR (electron spin resonance). 2244-11-3 belongs to class pyrimidines, and the molecular formula is C4H4N2O5, Computed Properties of 2244-11-3.

Elston, C.; Holmes, D. E.; Moorthy, P. N.; Pleticha-Lansky, R. published the artcile< Effects of γ-radiation on alloxantin. Polarographic, oscillopolarographic, and electron spin resonance studies>, Computed Properties of 2244-11-3, the main research area is alloxantin irradiation ESR.

Polarographic and oscillopolarographic investigation of the effects of γ-radiation on an aqueous solution of alloxantin showed the formation of alloxan, parabanic acid, and oxaluric acid. In addition an unidentified product X was observed, exhibiting cathodic wave at E1/2≈-1 V on polarography in acetate buffer of pH 3.6. This product is due probably to a higher oxidation state of alloxan and undergoes polarographic reduction at more neg. potentials than parabanic acid. ESR signals have been observed in γ-irradiated polycrystalline alloxantin-dihydrate, alloxan-monohydrate, dialuric acid, and parabanic acid. The G-values for the formation of the radicals responsible for these signals were determined Signals were also observed from organic free radicals formed through the reactions of electrons induced in irradiated H2SO4 ices containing alloxantin and alloxan.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Woodring, Jennifer L’s team published research in European Journal of Medicinal Chemistry in 2018-05-25 | 3921-01-5

European Journal of Medicinal Chemistry published new progress about Antimalarials. 3921-01-5 belongs to class pyrimidines, and the molecular formula is C4H2Br2N2, Recommanded Product: 2,4-Dibromopyrimidine.

Woodring, Jennifer L.; Bachovchin, Kelly A.; Brady, Kimberly G.; Gallerstein, Mitchell F.; Erath, Jessey; Tanghe, Scott; Leed, Susan E.; Rodriguez, Ana; Mensa-Wilmot, Kojo; Sciotti, Richard J.; Pollastri, Michael P. published the artcile< Corrigendum to ""Optimization of physicochemical properties for 4-Anilinoquinazoline inhibitors of trypanosome proliferation"" [Eur. J. Med. Chem. 141 (2017) 446-459] [Erratum to document cited in CA167:595582]>, Recommanded Product: 2,4-Dibromopyrimidine, the main research area is anilinoquinazoline trypanosome inhibitor antimalarial malaria trypanosomiasis trypanosomicide erratum.

In the original publication, the acknowledgments section has information omitted; the correction is provided here.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Kamada, Yusuke’s team published research in Journal of Medicinal Chemistry in 2017-05-25 | 6554-61-6

Journal of Medicinal Chemistry published new progress about Antitumor agents (potential). 6554-61-6 belongs to class pyrimidines, and the molecular formula is C4H2Cl2N2, Safety of 4,5-Dichloropyrimidine.

Kamada, Yusuke; Sakai, Nozomu; Sogabe, Satoshi; Ida, Koh; Oki, Hideyuki; Sakamoto, Kotaro; Lane, Weston; Snell, Gyorgy; Iida, Motoo; Imaeda, Yasuhiro; Sakamoto, Junichi; Matsui, Junji published the artcile< Discovery of a B-Cell Lymphoma 6 Protein-Protein Interaction Inhibitor by a Biophysics-Driven Fragment-Based Approach>, Safety of 4,5-Dichloropyrimidine, the main research area is drug screening lymphoma protein interaction inhibitor.

B-cell lymphoma 6 (BCL6) is a transcriptional factor that expresses in lymphocytes and regulates the differentiation and proliferation of lymphocytes. Therefore, BCL6 is a therapeutic target for autoimmune diseases and cancer treatment. This report presents the discovery of BCL6-corepressor interaction inhibitors by using a biophysics-driven fragment-based approach. Using the surface plasmon resonance (SPR)-based fragment screening, we successfully identified fragment 1 (SPR KD = 1200 μM, ligand efficiency (LE) = 0.28), a competitive binder to the natural ligand BCoR peptide. Moreover, we elaborated 1 into the more potent compound 7 (SPR KD = 0.078 μM, LE = 0.37, cell-free protein-protein interaction (PPI) IC50 = 0.48 μM (ELISA), cellular PPI IC50 = 8.6 μM (M2H)) by a structure-based design and structural integration with a second high-throughput screening hit.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Khamrai, Jagadish’s team published research in ACS Catalysis in 2020-03-20 | 89793-12-4

ACS Catalysis published new progress about Cross-coupling reaction catalysts. 89793-12-4 belongs to class pyrimidines, and the molecular formula is C7H7ClN2O2, Related Products of 89793-12-4.

Khamrai, Jagadish; Ghosh, Indrajit; Savateev, Aleksandr; Antonietti, Markus; Koenig, Burkhard published the artcile< Photo-Ni-Dual-Catalytic C(sp2)-C(sp3) Cross-Coupling Reactions with Mesoporous Graphitic Carbon Nitride as a Heterogeneous Organic Semiconductor Photocatalyst>, Related Products of 89793-12-4, the main research area is cross coupling reaction photocatalyst organic semiconductor nickel carbon nitride.

The synergistic combination of a heterogeneous organic semiconductor mesoporous graphitic carbon nitride (mpg-CN) and a homogeneous nickel catalyst with visible-light irradiation at room temperature affords the C(sp2)-C(sp3) cross-coupling of aryl halides and potassium alkyl trifluoroborates by single electron transmetallation. Like the homogeneously catalyzed protocol, the reaction is compatible with a variety of functional groups including electron-donating and electron-withdrawing aryl and heteroaryl moieties. Moreover, this protocol allows the installation of allyl groups onto (hetero)arenes, enlarging the scope of the method. The heterogeneous mpg-CN photocatalyst is easily recovered from the reaction mixture and reused several times, paving the way for larger-scale industrial applications of this type of photocatalytic bond-forming reactions.

ACS Catalysis published new progress about Cross-coupling reaction catalysts. 89793-12-4 belongs to class pyrimidines, and the molecular formula is C7H7ClN2O2, Related Products of 89793-12-4.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Li, Jian-Yuan’s team published research in Bioconjugate Chemistry in 2019-08-21 | 5018-38-2

Bioconjugate Chemistry published new progress about Carbonylation. 5018-38-2 belongs to class pyrimidines, and the molecular formula is C5H4Cl2N2O, Application of C5H4Cl2N2O.

Li, Jian-Yuan; Miklossy, Gabriella; Modukuri, Ram K.; Bohren, Kurt M.; Yu, Zhifeng; Palaniappan, Murugesan; Faver, John C.; Riehle, Kevin; Matzuk, Martin M.; Simmons, Nicholas published the artcile< Palladium-Catalyzed Hydroxycarbonylation of (Hetero)aryl Halides for DNA-Encoded Chemical Library Synthesis>, Application of C5H4Cl2N2O, the main research area is palladium catalyzed hydroxycarbonylation heteroaryl halide DNA encoded library synthesis.

A strategy for DNA-compatible, palladium-catalyzed hydroxycarbonylation of (hetero)aryl halides on DNA-chem. conjugates has been developed. This method generally provided the corresponding carboxylic acids in moderate to very good conversions for (hetero)aryl iodides and bromides, and in poor to moderate conversions for (hetero)aryl chlorides. These conditions were further validated by application within a DNA-encoded chem. library synthesis and subsequent discovery of enriched features from the library in selection experiments against two protein targets.

Bioconjugate Chemistry published new progress about Carbonylation. 5018-38-2 belongs to class pyrimidines, and the molecular formula is C5H4Cl2N2O, Application of C5H4Cl2N2O.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Prier, Christopher K’s team published research in Chemical Science in 2014 | 89793-12-4

Chemical Science published new progress about Aromatic heterocyclic amines Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (α-). 89793-12-4 belongs to class pyrimidines, and the molecular formula is C7H7ClN2O2, Related Products of 89793-12-4.

Prier, Christopher K.; MacMillan, David W. C. published the artcile< Amine α-heteroarylation via photoredox catalysis: a homolytic aromatic substitution pathway>, Related Products of 89793-12-4, the main research area is alpha heteroaryl amine regioselective preparation photoredox; tertiary amine heteroarene heteroarylation iridium.

The direct α-heteroarylation of tertiary amines has been accomplished via photoredox catalysis to generate valuable benzylic amine pharmacophores. A variety of five- and six-membered chloroheteroarenes are shown to function as viable coupling partners for the α-arylation of a diverse range of cyclic and acyclic amines. Evidence is provided for a homolytic aromatic substitution mechanism, in which a catalytically-generated α-amino radical undergoes direct addition to an electrophilic chloroarene.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Riederer, Heinz’s team published research in Journal of Physical Chemistry in 1981-09-17 | 4956-05-2

Journal of Physical Chemistry published new progress about ESR (electron spin resonance). 4956-05-2 belongs to class pyrimidines, and the molecular formula is C3H2BrN3O2, Electric Literature of 4956-05-2.

Riederer, Heinz; Huettermann, Juergen; Symons, Martyn C. R. published the artcile< Matrix-isolation of free radicals from 5-halouracils. 2. Electron spin resonance of hydrogen atom reactions in acidic glasses>, Electric Literature of 4956-05-2, the main research area is hydrogen atom nucleic acid constituent; nucleoside hydrogen atom; nucleotide hydrogen atom; uracil hydrogen atom; ESR nucleic acid constituent; radical nucleic acid constituent.

The reaction of H· atoms produced in acidic glasses (H2SO4 and H3PO4) by radiolysis and photolysis with the nucleic acid constituents by uracil, thymine, and the row of 5-halo-substituted uracils as well as their nucleoside (nucleotide) derivatives and deoxyribose were studied by ESR spectroscopy. With the pyrimidines, addition at either site of the 5,6 double bond was the only reaction, the relative yield of 5-yl or 6-yl radicals depending largely on the nature of the nonhydrogen 5 or 6 substituent. The spectral parameters of both radical types were determined by spectra simulation. In deoxyribose, abstraction of a carbon-bound hydrogen takes place from probably only 2 initial sites, the corresponding radicals undergoing a fast and a slow secondary reaction. In nucleosides (nucleotides), the base and deoxyribose (deoxyribose phosphate) moiety react independently. The relative yield of both subgroup radicals was determined and explained in terms of a “”miss or react”” mechanism. The findings are discussed in terms of solid-state vs. liquid solution type reaction mechanisms.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia