Category: pyrimidines

Sana, Sravani published the artcileCinnamide derived pyrimidine-benzimidazole hybrids as tubulin inhibitors: Synthesis, in silico and cell growth inhibition studies, Recommanded Product: 2-Amino-4,6-dichloropyrimidine, the publication is Bioorganic Chemistry (2021), 104765, database is CAplus and MEDLINE.

A new class of piperazine-linked cinnamide derivatives of benzimidazole-pyrimidine hybrids have been synthesized and their in vitro cytotoxicity profiles were explored on selected human cancer cell lines. Specifically, structural comparison of target hybrids with tubulin-DAMA-colchicine and tubulin-nocodazole complexes has exposed a deep position of benzimidazole ring into the αT5 loop. The utmost cytotoxicity has shown with an amine linker of benzimidazole-pyrimidine series, with toward A549 (lung cancer) cell line. The most potent compound in this series was 18i, which inhibited cancer cell growth at micromolar concentrations ranging 2.21-7.29μM. Flow cytometry studies disclosed that compound I inhibited the cells in G2/M phase of cell cycle. The most active compound I also inhibited tubulin polymerization with an IC50 of 5.72 ± 0.51μM. In vitro biol. anal. of compound I presented apoptosis induction on A549 cells with triggering of ROS generation and loss of mitochondrial membrane potential, resulting in DNA injury. In addition, compound I displayed impairment in cellular migration and inhibited the colony formation. Notably, the safety profile of most potent compound 18i was revealed by screening against normal human pulmonary epithelial cells (L132: IC50: 69.25 ± 5.95μM). The detailed binding interactions of compound I with tubulin was investigated by employing mol. docking, superimposition and free energy analyses.

Bioorganic Chemistry published new progress about 56-05-3. 56-05-3 belongs to pyrimidines, auxiliary class Pyrimidine,Chloride,Amine,API, name is 2-Amino-4,6-dichloropyrimidine, and the molecular formula is C4H3Cl2N3, Recommanded Product: 2-Amino-4,6-dichloropyrimidine.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Qiu, Yan published the artcileDesign and synthesis of uracil urea derivatives as potent and selective fatty acid amide hydrolase inhibitors, Recommanded Product: 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is RSC Advances (2017), 7(37), 22699-22705, database is CAplus.

Fatty acid amide hydrolase (FAAH) is one of the key enzymes involved in the biol. degradation of endocannabinoids, especially anandamide. Pharmacol. blockage of FAAH restores the levels of endocannabinoids, providing therapeutic benefits in the management of inflammation, depression and multiple sclerosis. In this study, a series of uracil urea derivatives as FAAH inhibitors were designed and synthesized. Structural modifications at the C5 position and side chain of N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide (1a) led to FAAH inhibitors with improved potency and selectivity. Structure-activity relationship (SAR) studies indicated that C5 electron-withdrawing substituents were preferred for optimal potency but not for selectivity, whereas replacement of the alkyl chain with phenylalkyl moieties or biphenyl groups significantly improved both inhibitory potency and selectivity towards FAAH. Two highly potent picomolar FAAH inhibitors (4c, IC₅₀ = 0.3 ± 0.05 nM; 4d, IC₅₀ = 0.8 ± 0.1 nM) were developed. Compound 4c inhibited FAAH in a rapid, selective, noncompetitive, and irreversible pattern. This study provides several highly potent and selective FAAH inhibitors and an optimized chem. scaffold for the development of FAAH inhibitors. We anticipate that these FAAH inhibitors will enable new possibilities in understanding FAAH functions and development of therapeutics for pain and inflammatory diseases.

RSC Advances published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C5H6N2O2, Recommanded Product: 3-Methylpyrimidine-2,4(1H,3H)-dione.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Fischbach, Melanie published the artcileProtease Probes that Enable Excimer Signaling upon Scission, COA of Formula: C26H26N4O7, the publication is Angewandte Chemie, International Edition (2014), 53(44), 11955-11959, database is CAplus and MEDLINE.

Peptide-based probes that fluoresce upon proteolytic cleavage are invaluable tools for monitoring protease activity. The read-out of protease activity through pyrene excimer signaling would be a valuable asset because the large Stokes shift and the long lifetime of the excimer emission facilitate measurements in autofluorescent media such as blood serum. However, proteolytic cleavage abolishes rather than installs the proximity relations required for excimer signaling. Herein, the authors introduce a new probe architecture to enable the switching on of pyrene excimer emission upon proteolytic scission. The method relies on hairpin-structured peptide nucleic acid (PNA)/peptide hybrids with pyrene units and anthraquinone-based quencher residues positioned in a zipper-like arrangement within the PNA stem. The excimer hairpin peptide beacons afforded up to a 50-fold enhancement of the pyrene excimer emission. Time-resolved measurements allowed the detection of matrix metalloprotease 7 in human blood serum.

Angewandte Chemie, International Edition published new progress about 169396-92-3. 169396-92-3 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Amide,Others,PNA, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C26H26N4O7, COA of Formula: C26H26N4O7.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Fischbach, Melanie published the artcileProtease Probes that Enable Excimer Signaling upon Scission, Quality Control of 186046-81-1, the publication is Angewandte Chemie, International Edition (2014), 53(44), 11955-11959, database is CAplus and MEDLINE.

Peptide-based probes that fluoresce upon proteolytic cleavage are invaluable tools for monitoring protease activity. The read-out of protease activity through pyrene excimer signaling would be a valuable asset because the large Stokes shift and the long lifetime of the excimer emission facilitate measurements in autofluorescent media such as blood serum. However, proteolytic cleavage abolishes rather than installs the proximity relations required for excimer signaling. Herein, the authors introduce a new probe architecture to enable the switching on of pyrene excimer emission upon proteolytic scission. The method relies on hairpin-structured peptide nucleic acid (PNA)/peptide hybrids with pyrene units and anthraquinone-based quencher residues positioned in a zipper-like arrangement within the PNA stem. The excimer hairpin peptide beacons afforded up to a 50-fold enhancement of the pyrene excimer emission. Time-resolved measurements allowed the detection of matrix metalloprotease 7 in human blood serum.

Angewandte Chemie, International Edition published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C39H35N5O8, Quality Control of 186046-81-1.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Hinton, Shante published the artcileDeoxy derivatives of L-like 5′-noraristeromycin, Related Products of pyrimidines, the publication is Tetrahedron Letters (2012), 53(14), 1753-1755, database is CAplus and MEDLINE.

Several base variations of 2′- and 3′-deoxy derivatives of (+)-4′-deoxy-5′-noraristeromycin have been prepared from enantiomerically pure precursors following standard purine nucleoside construction. These carbocyclic nucleosides were evaluated against hepatitis B virus (HBV) and found to be inactive. No cytotoxicity to the cell line was observed

Tetrahedron Letters published new progress about 56-05-3. 56-05-3 belongs to pyrimidines, auxiliary class Pyrimidine,Chloride,Amine,API, name is 2-Amino-4,6-dichloropyrimidine, and the molecular formula is C4H3Cl2N3, Related Products of pyrimidines.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Yang, Zhibo published the artcileInfluence of methylation on the properties of uracil and its noncovalent interactions with alkali metal ions. Threshold collision-induced dissociation and theoretical studies, Application In Synthesis of 608-34-4, the publication is International Journal of Mass Spectrometry (2005), 241(2-3), 225-242, database is CAplus.

The influence of methylation on the properties of uracil and its noncovalent interactions with alkali metal ions is investigated both exptl. and theor. Threshold collision-induced dissociation (CID) of M⁺(xMeU) with Xe is studied in a guided ion beam mass spectrometer. M⁺ include the following alkali metal ions: Li⁺, Na⁺, and K⁺. Five methylated uracils are examined, xMeU = 1-methyluracil, 3-methyluracil, 6-methyluracil, 1,3-dimethyluracil, and 5,6-dimethyluracil. In all cases endothermic loss of the intact nucleobase is the dominant reaction pathway, while ligand exchange to produce MXe⁺ is observed as a minor reaction pathway. The threshold regions of the cross sections are interpreted to extract 0 and 298 K bond dissociation energies (BDEs) for M⁺-xMeU after accounting for the effects of multiple ion-neutral collisions, kinetic and internal energies of the reactants, and dissociation lifetimes. Ab initio calculations at the MP2(full)/6-31G* level of theory are used to determine the structures of these complexes and provide mol. constants required for the thermochem. anal. of the exptl. data. Theor. bond dissociation energies are determined from single point energy calculations at the MP2(full)/6-211+G(2d,2p) level using the MP2(full)/6-31G* geometries. Excellent agreement between theory and experiment is found for the Na⁺ and K⁺ systems, while theory systematically underestimates the strength of binding in the Li⁺ systems. Theor. calculations are also performed to examine the influence of methylation on the acidities, proton affinities, and Watson-Crick base pairing energies. The present results are compared to earlier studies of uracil and 5-methyluracil to more fully elucidate the influence of methylation on the properties of uracil, its noncovalent interactions with alkali metal ions, and nucleic acid stability.

International Journal of Mass Spectrometry published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C20H40O2, Application In Synthesis of 608-34-4.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Liu, Yang published the artcileInducible Alkylation of DNA by a Quinone Methide-Peptide Nucleic Acid Conjugate, Synthetic Route of 169396-92-3, the publication is Biochemistry (2012), 51(5), 1020-1027, database is CAplus and MEDLINE.

The reversibility of alkylation by a quinone methide intermediate (QM) avoids the irreversible consumption that plagues most reagents based on covalent chem. and allows for site specific reaction that is controlled by the thermodn. rather than kinetics of target association This characteristic was originally examined with an oligonucleotide QM conjugate, but broad application depends on alternative derivatives that are compatible with a cellular environment. Now, a peptide nucleic acid (PNA) derivative has been constructed and shown to exhibit an equivalent ability to deliver the reactive QM in a controlled manner. This new conjugate demonstrates high selectivity for a complementary sequence of DNA even when challenged with an alternative sequence containing a single T/T mismatch. Alternatively, alkylation of noncomplementary sequences is only possible when a template strand is present to colocalize the conjugate and its target. For efficient alkylation in this example, a single-stranded region of the target is required adjacent to the QM conjugate. Most importantly, the intrastrand self-adducts formed between the PNA and its attached QM remained active and reversible over more than 8 days in aqueous solution prior to reaction with a chosen target added subsequently.

Biochemistry published new progress about 169396-92-3. 169396-92-3 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Amide,Others,PNA, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C26H26N4O7, Synthetic Route of 169396-92-3.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Grabowski, Zbigniew R. published the artcileTwisted intramolecular charge transfer states (TICT). A new class of excited states with a full charge separation, COA of Formula: C6H9N3, the publication is Nouveau Journal de Chimie (1979), 3(7), 443-54, database is CAplus.

The dual fluorescence of N,N-dialkylanilines as well as the high polarity of the lowest excited singlet states of compounds containing perpendicular donor (D) and acceptor (A) orbitals is explained by a common phenomenon involving 1 electron transfer in this new class of excited states, TICT. The electronic structure, thermodn. and formation kinetics, dipole moments, and radiative and radiationless transitions of the TICT states are discussed. The TICT states are formed by D-A mols. as well as sym. biaryls and I.

Nouveau Journal de Chimie published new progress about 31401-45-3. 31401-45-3 belongs to pyrimidines, auxiliary class Pyrimidine,Amine, name is N,N-Dimethylpyrimidin-4-amine, and the molecular formula is C6H9N3, COA of Formula: C6H9N3.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Pizzirani, Daniela published the artcileDiscovery of a New Class of Highly Potent Inhibitors of Acid Ceramidase: Synthesis and Structure-Activity Relationship (SAR), Product Details of C5H6N2O2, the publication is Journal of Medicinal Chemistry (2013), 56(9), 3518-3530, database is CAplus and MEDLINE.

1-(Alkylamino)-2,4-pyrimidinediones such as I [R = H, F, MeO, F₃C, Ph; R¹ = Me(CH₂)_nNH; R² = H, Me, MeO₂C; n = 5, 7] were prepared as inhibitors of acid ceramidase for potential use as antitumor agents. Uracils bearing an electron-withdrawing substituent at position 5, a substituent such as Me at position 3, and an alkylaminocarbonyl moiety with a six- to eight-carbon alkyl group at position 1 were the most effective inhibitors of acid ceramidase of the compounds tested. The acid ceramidase inhibition and stability of an alkylaminopyrimidinedione was correlated with the stabilization of the antibonding orbital of its N1-carbonyl bond. I (R = H, F, Ph; R² = H, Me; n = 5, 7) inhibited a human cancer cell line (SW403) with IC₅₀ values of 20-24 μM. I (R = F, F₃C, MeO; R² = H, MeO₂C; n = 5, 7) inhibited acid ceramidase with single digit-nanomolar IC₅₀ values (IC₅₀ = 4-7 nM).

Journal of Medicinal Chemistry published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C5H6N2O2, Product Details of C5H6N2O2.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Zhang, Jing-Wen published the artcileDonor-acceptor carbon nitride with electron-withdrawing chlorine group to promote exciton dissociation, Name: 2-Amino-4,6-dichloropyrimidine, the publication is Chinese Journal of Catalysis (2021), 42(7), 1168-1175, database is CAplus.

Carbon nitride (C₃N₄) is promising for photocatalytic hydrogen production, but photogenerated electrons and holes in C₃N₄ usually tend to exist as excitons due to intrinsic Coulomb interactions making its photocatalytic activity unsatisfactory. Herein, a well-designed intramol. C₃N₄-based donor-acceptor (D-A) photocatalytic system was constructed to promote exciton dissociation Due to its good chem. compatibility with melamine and appropriate sublimation property, 2-amino-4,6-dichloropyrimidine unit was chosen as the monomer to react with melamine to construct intramol. D-A system (CNCl_x). The hydrogen evolution rate of CNCl_0.15 is 15.3 times higher than that of bulk C₃N₄ under visible light irradiation, with apparent quantum efficiency of 13.6% at 420 nm. The enhanced activity is attributed to introduced electron-withdrawing -Cl group as terminal group in the resulted CNCl_x samples, which can build internal elec. field to promote the exciton dissociation into free electron and hole. In addition, lower work function value of CNCl_x samples indicates that internal elec. field can help free electrons and holes transfer to the surface of CNCl_x samples for photocatalytic reaction.

Chinese Journal of Catalysis published new progress about 56-05-3. 56-05-3 belongs to pyrimidines, auxiliary class Pyrimidine,Chloride,Amine,API, name is 2-Amino-4,6-dichloropyrimidine, and the molecular formula is C15H14O3, Name: 2-Amino-4,6-dichloropyrimidine.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia