Tag: M.W=100-150

Dekker, J. published the artcile< Effect of kinetin on powdery mildew>, COA of Formula: C4H2Cl2N2, the main research area is .

Kinetin (10-20 p.p.m.) solution completely checked the development of various varieties of powdery mildew on different plant leaves. The tests were made by floating leaf disks on the solutions Kinetin was ineffective against other fungi tested. The two components of kinetin (adenine and furfuryl alc.) showed no activity against powdery mildew, singly or in combination. However, out of about 80 purines and pyrimidines tested, 6-azauracil appeared highly active.

Nature (London, United Kingdom) published new progress about Mildew (plant disease). 6554-61-6 belongs to class pyrimidines, and the molecular formula is C4H2Cl2N2, COA of Formula: C4H2Cl2N2.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Chesterfield, J.; McOmie, J. F. W.; Sayer, E. R. published the artcile< Pyrimidines. VIII. Halo- and hydrazinopyrimidines>, SDS of cas: 6554-61-6, the main research area is .

Cl (1.5 g.) was bubbled into 2.0 g. 4-hydroxypyrimidine in 15 ml. glacial HOAc, the HCl salt collected and dissolved in H2O, and NaHCO3 added until the solution was faintly alk. to give 0.8 g. 5-Cl derivative (I), m. 177-9° (from H2O). 4-Hydroxypyrimidine was likewise brominated to give the HBr salt of the 5-Br derivative, m. 243-6° (decomposition) (from EtOH), which recrystallized from H2O yielded the free base (II), m. 199-200°. 2-Amino-5-bromopyrimidine (2 g.) was diazotized (with H2SO4, NaNO2) to yield 0.5 g. 2-HO analog (III), m. 241-3° (from H2O). A mixture of 3 g. II, 22 ml. POCl3, and 0.7 ml. PhNMe2 were heated 3 hrs., cooled, poured onto ice, and extracted with Et2O to obtain the 4-Cl analog, b16 87°. In the same way I was converted in 48% yield to 4,5-dichloropyrimidine, b34 82°, which, after a month changed to a bright yellow solid. Cl bubbled into a suspension of 5.6 g. uracil in 100 ml. H2O at 80-5° until the solid had dissolved and another precipitated yielded 4.0 g. 5-chlorouracil (IV), m. 314-18° (decomposition) (from H2O). Cl bubbled into a mixture of 5.0 g. uracil in 40 ml. H2O on a boiling H2O bath yielded 5,5-dichloro-5,6-dihydro-6-hydroxyuracil, m. 216-18° (slight decomposition) (from H2O). IV treated with POCl3 and PCl5 on a steam bath and then at 135-40° 24 hrs. and the mixture distilled gave 2,4,5-trichloropyrimidine, b3 73-4°. 4,6-Dihydroxypyrimidine (IVa) (12 g.) was brominated in HOAc, yielding 10.5 g. 5-Br derivative (V), m. 263-4° (decomposition) (from H2O). Iodine chloride in HOAc was added to a suspension of 5.6 g. IVa in HOAc, the mixture heated on a steam bath 2.5 hrs. and cooled, and the residue crystallized from H2O gave 3.8 g. 5-Cl derivative (VI), decomposing above 230°. V with POCl3 and PhNMe2 yielded 46% 5-bromo-4,6-dichloropyrimidine, m. 75-6°. Similarly, VI gave 77% 4,5,6-trichloropyrimidine (VII), m. 49-51°. EtOH was added to 3 g. 5-bromo-4-chloropyrimidine and 15 ml. aqueous NH3 (d. 0.88) to give a homogeneous solution; after 48 hrs., the precipitate was collected and recrystallized twice from H2O to give 41% 4-H2N analog, m. 208-10 ° (decomposition). In the same way, 4,5-dichloropyrimidine (VIII) gave 65% 4-H2N analog, m. 192-4°. A solution of 0.6 g. VIII and 0.4 g. thiourea in 25 ml. EtOH was boiled 1 hr., concentrated to 12 ml. and cooled to obtain 68% 4-HS analog, m. 212° (slight decomposition) (from EtOH). 2,4,5-Trichloropyrimidine (5.8 g.) was added slowly to a solution of NaOMe (from 5 g. Na and 100 ml. MeOH), the mixture boiled 15 min., cooled, and filtered, the filtrate saturated with CO2 and filtered, the residues extracted with Et2O, and the Et2O solution combined with the MeOH solution Distillation and sublimation at 100°/11 mm. gave 74% 5-chloro-2,4-dimethoxypyrimidine, m. 72-3°. 2-Methoxypyrimidine, N2H4.H2O, and MeOH were heated 2 hrs., the MeOH removed and the precipitate, which formed in a few days, recrystallized from MeOH-C6H6 to give 2-hydrazinopyrimidine, m. 108-10°, after thorough drying. 4-Methoxypyrimidine, was similarly converted to 55% 4-hydrazinopyrimidine, m. 132-4° (decomposition). N2H4.H2O was added gradually to 4,5-dichloropyrimidine in EtOH to give 38% 4-H2NNH analog, m. 190-2° (from H2O). Similarly, 5-bromo-4-chloropyrimidine yielded 48% 4-H2NNH analog, m. 185-7° (decomposition); 4-chloro-5-phenylpyrimidine gave slowly 54% 4-H2NNH analog, m. 140-1°; 4,6-dichloropyrimidine gave 34% 4-H2NNH analog, m. 177° (decomposition); 2,4,5-trichloropyrimidine yielded 62% 4-H2NNH analog, which turned black above 220°; and 2-chloro-4-phenylpyrimidine gave 25% 2-H2NNH analog, m. 115°. The hydrazinopyrimidines were bacteriologically inactive.

Journal of the Chemical Society published new progress about 6554-61-6. 6554-61-6 belongs to class pyrimidines, and the molecular formula is C4H2Cl2N2, SDS of cas: 6554-61-6.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Ferris, J. P.; Joshi, P. C.; Edelson, E. H.; Lawless, J. G. published the artcile< Chemical evolution. XXX. Hydrogen cyanide: a plausible source of purines, pyrimidines and amino acids on the primitive earth>, Recommanded Product: 5-Hydroxypyrimidin-4(3H)-one, the main research area is hydrocyanate chem evolution; amino acid formation hydrocyanate prebiotic; pyrimidine formation hydrocyanate prebiotic; purine formation hydrocyanate prebiotic.

Dilute (0.1M) solutions of HCN condense to oligomers at pH 9.2. Hydrolysis of these oligomers yields 4,5-dihydroxypyrimidine, orotic acid, 5-hydroxyuracil, adenine, 4-aminoimidazole-5-carboxamide, and amino acids. These results, together with the earlier data, demonstrate that the 3 main classes of N-containing biomols., purines, pyrimidines, and amino acids may have originated from HCN on the primitive earth. The observation of orotic acid and 4-aminoimidazole-5-carboxamide suggests that the contemporary biosynthetic pathways for nucleotides may have evolved from the compounds released on hydrolysis of HCN oligomers.

Journal of Molecular Evolution published new progress about Amino acids Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 15837-41-9 belongs to class pyrimidines, and the molecular formula is C4H4N2O2, Recommanded Product: 5-Hydroxypyrimidin-4(3H)-one.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.

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.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Miyakawa, Shin; Yamanashi, Hiroto; Kobayashi, Kensei; Cleaves, H. James; Miller, Stanley L. published the artcile< Prebiotic synthesis from CO atmospheres: implications for the origins of life>, Related Products of 15837-41-9, the main research area is carbon monoxide primordial atm prebiotic amino acid life origin.

Most models of the primitive atm. around the time life originated suggest that the atm. was dominated by carbon dioxide, largely based on the notion that the atm. was derived via volcanic outgassing, and that those gases were similar to those found in modern volcanic effluent. These models tend to downplay the possibility of a strongly reducing atm., which had been thought to be important for prebiotic synthesis and thus the origin of life. However, there is no definitive geol. evidence for the oxidation state of the early atm. and bioorganic compounds are not efficiently synthesized from CO2 atmospheres. In the present study, proton-beam irradiation of equimol. mixtures of CO and N2 in the presence of water induced abiotic synthesis of uracil, orotic acid, 5-hydroxyuracil, nicotinic acid, and 4,5-dihydroxypyrimidine. This and similar previous observations suggest that a CO-CO2-N2-H2O atm. can give a variety of bioorganic compounds with yields comparable to those obtained from a strongly reducing atm. Atmospheres containing carbon monoxide might therefore have been conducive to prebiotic synthesis and perhaps the origin of life. CO-dominant atmospheres could have existed if the production rate of CO from impacts of extraterrestrial materials were high or if the upper mantle had been more reduced than today.

Proceedings of the National Academy of Sciences of the United States of America published new progress about Life, origin. 15837-41-9 belongs to class pyrimidines, and the molecular formula is C4H4N2O2, Related Products of 15837-41-9.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Homon, Anton A.; Hryshchuk, Oleksandr V.; Trofymchuk, Serhii; Michurin, Oleg; Kuchkovska, Yuliya; Radchenko, Dmytro S.; Grygorenko, Oleksandr O. published the artcile< Synthesis of 3-Azabicyclo[3.2.0]heptane-Derived Building Blocks via [3+2] Cycloaddition>, Application In Synthesis of 6554-61-6, the main research area is azabicyclo heptane derivative; cyclobuteneraboxylic acid ester cycloaddition.

An efficient approach to synthesis of various substituted 3-azabicyclo[3.2.0]heptane-derived building blocks based on [3+2] cycloaddition of cyclobut-1-eneraboxylic acid ester and in situ generated azomethine ylide was developed and applied on multigram scale. The utility of 1,3-disubstituted 3-azabicyclo[3.2.0]heptane scaffold was demonstrated by addnl. structural anal. using exit vector plot (EVP) tool, and tested in parallel synthesis of compound library.

European Journal of Organic Chemistry published new progress about [3+2] Cycloaddition reaction. 6554-61-6 belongs to class pyrimidines, and the molecular formula is C4H2Cl2N2, Application In Synthesis of 6554-61-6.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

O’Brien, Darrell E.; Springer, Robert H.; Cheng, C. C. published the artcile< New Mannich reaction of pyrimidines>, Safety of 5-Hydroxypyrimidin-4(3H)-one, the main research area is .

4,5-Dihydroxypyrimidines undergo the Mannich reaction with primary and secondary amines and CH2O at the 6-position. 5-Hydroxy-6-piperidinomethyluracil, 3,6-dimethyl-3,4-dihydro-2H-pyrimido[4,5-e]-1,3-oxazin-8-ol (I, R = Me), and the 6-OH analog of I were prepared in this manner. The new Mannich reaction appears to be a general method for the synthesis of compounds containing the new 3,4-dihydro-2H-pyrimido[4,5-e]-1,3-oxazine ring system.

Journal of Heterocyclic Chemistry published new progress about Mannich reaction. 15837-41-9 belongs to class pyrimidines, and the molecular formula is C4H4N2O2, Safety of 5-Hydroxypyrimidin-4(3H)-one.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Cleaves, H. James II published the artcile< The Reactions of Nitrogen Heterocycles with Acrolein: Scope and Prebiotic Significance>, Name: 5-Hydroxypyrimidin-4(3H)-one, the main research area is acrolein nucleobase adduct Michael addition prebiotic evolution.

It was suggested that life began with a self-replicating RNA mol. However, after much research into the prebiotic synthesis of RNA, the difficulties encountered have lead some to hypothesize that RNA was preceded by a simpler mol., 1 more easily synthesized prebiotically. Many of the proposed alternative mols. are based on acrolein, since it reacts readily with nucleophiles, such as the nucleobases, via Michael addition and is readily synthesized from formaldehyde and acetaldehyde. Reports regarding the reactions of nucleobases with concentrated acrolein solutions suggest that this is a plausible reaction mechanism, though there are also reports that the “”incorrect”” isomers are obtained. The scope and kinetics of the reaction of acrolein with various nitrogen heterocycles are reported here. Reactions of pyrimidines often give N1 adducts as the major products. Reactions of purines often give N9 adducts in good yield. The reactions are rapid under neutral to slightly alk. conditions, and proceed at low temperatures and dilutions The implications of these findings for the origin of life are discussed.

Astrobiology published new progress about Addition compounds. 15837-41-9 belongs to class pyrimidines, and the molecular formula is C4H4N2O2, Name: 5-Hydroxypyrimidin-4(3H)-one.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Sodum, Rama S.; Klein, Robert S.; Otter, Brian A. published the artcile< Chemistry of 4-pyrimidinones: acetylation and ring-opening reactions>, Name: 5-Hydroxypyrimidin-4(3H)-one, the main research area is pyrimidinone acetylation ring cleavage.

4(3H)-Pyrimidinone (I), as well as its 5-acetoxy and 5-methoxy derivatives, undergoes selective acetylation at N-1 when treated with acetic anhydride. In the presence of water, these 1-acetylpyrimidines undergo spontaneous covalent hydration at C-2 and cleavage of the 1,2-bond to give crystalline cis-3-acetylamino-N-formylacrylamides, generally in good yield. In contrast, the 6-Me derivative of 4(3H)-pyrimidinone forms an equilibrium mixture of acetylated products that undergo the ring opening process to only a very limited extent, the major product (11%) being 3-formylamino-N-acetylacrylamide derivative formed via N-3 acetylation and cleavage of the 2,3-bond.

Journal of Heterocyclic Chemistry published new progress about Acetylation. 15837-41-9 belongs to class pyrimidines, and the molecular formula is C4H4N2O2, Name: 5-Hydroxypyrimidin-4(3H)-one.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Regan, Collin F.; Pierre, Fabrice; Schwaebe, Michael K.; Haddach, Mustapha; Jung, Michael E.; Ryckman, David M. published the artcile< A facile synthesis of 5-halopyrimidine-4-carboxylic acid esters via a Minisci reaction>, Synthetic Route of 6554-61-6, the main research area is Minisci homolytic alkoxycarbonylation halopyrimidine; bromopyrimidinecarboxylate; pyrimidine halo Minisci homolytic alkoxycarbonylation.

This paper reports the synthesis of various 5-halopyrimidine-4-carboxylic acid esters via the Minisci homolytic alkoxycarbonylation of 5-halopyrimidines. The reaction was found to be highly regioselective, allowing the one-step synthesis of useful amounts (>10 g) of Et 5-bromopyrimidine-4-carboxylate where other methods proved difficult. Et 5-bromopyrimidine-4-carboxylate was used for the preparation of potent CK2 inhibitors including CX-5011. This work represents an interesting application of radical chem. for the preparation of pharmacol. active mols.

Synlett published new progress about Alkoxycarbonylation (Minisci homolytic). 6554-61-6 belongs to class pyrimidines, and the molecular formula is C4H2Cl2N2, Synthetic Route of 6554-61-6.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia