Month: April 2022

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Uracil-Directed Ligand Tethering: An Efficient Strategy for Uracil DNA Glycosylase (UNG) Inhibitor Development, published in 2005-12-14, which mentions a compound: 2689-65-8, Name is 5-Iodo-2-furaldehyde, Molecular C5H3IO2, Application of 2689-65-8.

Uracil DNA glycosylase (UNG) is an important DNA repair enzyme that recognizes and excises uracil bases in DNA using an extrahelical recognition mechanism. It is emerging as a desirable target for small-mol. inhibitors given its key role in a wide range of biol. processes including the generation of antibody diversity, DNA replication in a number of viruses, and the formation of DNA strand breaks during anticancer drug therapy. To accelerate the discovery of inhibitors of UNG we have developed a uracil-directed ligand tethering strategy. In this efficient approach, a uracil aldehyde ligand is tethered via alkyloxyamine linker chem. to a diverse array of aldehyde binding elements. Thus, the mechanism of extrahelical recognition of the uracil ligand is exploited to target the UNG active site, and alkyloxyamine linker tethering is used to randomly explore peripheral binding pockets. Since no compound purification is required, this approach rapidly identified the first small-mol. inhibitors of human UNG with micromolar to submicromolar binding affinities. In a surprising result, these uracil-based ligands are found not only to bind to the active site but also to bind to a second uncompetitive site. The weaker uncompetitive site suggests the existence of a transient binding site for uracil during the multistep extrahelical recognition mechanism. This very general inhibitor design strategy can be easily adapted to target other enzymes that recognize nucleobases, including other DNA repair enzymes that recognize other types of extrahelical DNA bases.

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1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

COA of Formula: C5H3IO2. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 5-Iodo-2-furaldehyde, is researched, Molecular C5H3IO2, CAS is 2689-65-8, about Site-Selective C-S Bond Formation at C-Br over C-OTf and C-Cl Enabled by an Air-Stable, Easily Recoverable, and Recyclable Palladium(I) Catalyst. Author is Scattolin, Thomas; Senol, Erdem; Yin, Guoyin; Guo, Qianqian; Schoenebeck, Franziska.

This report widens the repertoire of emerging PdI catalysis to carbon-heteroatom, i.e., C-S bond formation. While Pd0-catalyzed protocols may suffer from the formation of poisonous sulfide-bound off-cycle intermediates and lack of selectivity, the mechanistically diverse PdI catalysis concept circumvents these challenges and allows for C-S bond formation (S-aryl and S-alkyl) of a wide range of aryl halides. Site-selective thiolations of C-Br sites in the presence of C-Cl and C-OTf were achieved in a general and a priori predictable fashion. Computational, spectroscopic, x-ray, and reactivity data support dinuclear PdI catalysis to be operative. Contrary to air-sensitive Pd0, the active PdI species was easily recovered in the open atm. and subjected to multiple rounds of recycling.

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1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

HPLC of Formula: 1569-17-1. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 4-Methyl-1,8-naphthyridine, is researched, Molecular C9H8N2, CAS is 1569-17-1, about Hydrogen-deuterium exchange in 1,8-naphthyridine and some its monosubstituted derivatives. Author is Wozniak, Marian.

Hydrogen-deuterium exchange in 1,8-naphthyridine and 10 of its derivatives containing Me, hydroxy, amino, nitro and chloro substituents are reported. A discussion of the factors influencing the relative positional reactivity toward deuterium in these compounds is presented.

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1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 5-Iodo-2-furaldehyde( cas:2689-65-8 ) is researched.Electric Literature of C5H3IO2.Kaigorodova, E.A.; Kvak, S. N.; Ugrak, B. I.; Zaplishnyi, V. N.; Kul’nevich, V. G. published the article 《Studies on furopyridines. VI. Synthesis and stereostructure of hetarylmethylene-3-oxo-4-thiofuro[3,4-c]pyridines》 about this compound( cas:2689-65-8 ) in Zhurnal Organicheskoi Khimii. Keywords: furopyridine thio hetarylmethylene preparation stereochem; regioselective condensation heteroaromatic aldehyde thiofuropyridine. Let’s learn more about this compound (cas:2689-65-8).

Condensation reaction of 6-methyl-3-oxo-4-thio-1H-furo[3,4-c]pyridine with heteroaromatic aldehydes proceeds regioselectively at the methylene center to give Z isomers of title compounds I (R = H, Z = O, S; R = Me, Br, iodo, Z = O) in s-cis conformations for furfuryl and in s-trans conformations for thenylmethylene derivatives

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1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 5-Iodo-2-furaldehyde, is researched, Molecular C5H3IO2, CAS is 2689-65-8, about Formation of α-chiral centers by asymmetric β-C(sp3)-H arylation, alkenylation, and alkynylation.Product Details of 2689-65-8.

The enzymic β-C-H hydroxylation of the feedstock chem. isobutyric acid has enabled the asym. synthesis of a wide variety of polyketides. The analogous transition metal-catalyzed enantioselective β-C-H functionalization of isobutyric acid-derived substrates should provide a versatile method for constructing useful building blocks with enantioenriched α-chiral centers from this abundant C-4 skeleton. However, the desymmetrization of ubiquitous iso-Pr moieties by organometallic catalysts has remained an unanswered challenge. Herein, the authors report the design of chiral mono-protected aminomethyl oxazoline ligands that enable desymmetrization of iso-Pr groups via palladium insertion into the C(sp3)-H bonds of one of the prochiral Me groups. We detail the enantioselective β-arylation, -alkenylation, and -alkynylation of isobutyric acid/2-aminoisobutyric acid derivatives, which may serve as a platform for the construction of α-chiral centers.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Rodgriguez, M.; Fernandez Bertran, J. published the article 《Solvent effect on rotational isomerism of furfural and its 5-substituted derivatives》. Keywords: solvent effect isomerism furfural; substituent effect isomerism furfural; rotamer population furfural; coupling constant furfural; PMR solvent effect furfural.They researched the compound: 5-Iodo-2-furaldehyde( cas:2689-65-8 ).Formula: C5H3IO2. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:2689-65-8) here.

The solvent effect on the rotamer distribution of I (R = H) was determined from the 5Jα,4 and the 6Jα,5 in the PMR; 5Jn was inversely proportional to 6J. Polar solvents favored the cis-OO population. The substituent effect on the equilibrium was determined from the 5J for I (R = NO2, Cl, Br, I, Me2N); electron donating substituents also favored the cis-OO rotamer.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Furan derivatives. LV. Kinetics of condensation of 5-nitrofurfuryl sulfones with aldehydes, published in 1975, which mentions a compound: 2689-65-8, mainly applied to kinetics condensation aldehyde nitrofurfuryl sulfone; substituent effect condensation aldehyde nitrofurfuryl sulfone; reaction constant condensation aldehyde nitrofurfuryl sulfone; furfuryl sulfone condensation aldehyde nitrofurfuryl sulfone, Product Details of 2689-65-8.

The kinetics of the condensation of I with II (R = H, Me, iodo, Cl, Br, CO2Me NO2) or III (R = H, NO2, Cl, Br, CO2H, CO2Et, Me, MeO, NHAc) [to give, resp., the corresponding (E)-IV or (E)-V, examined in NH4OAc-piperidine at 118° or MeOH-piperidine at 40°, were 2nd order. The log k was linearly related with σp+. The pKa of I and of 5-nitrofurfuryl Me sulfone (VI) were determined and the rates of the condensation of I or VI with III (R = NO2) indicated that steric factors were more important in the condensation than was the sulfone acidity.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 2689-65-8, is researched, SMILESS is IC1=CC=C(O1)C=O, Molecular C5H3IO2Journal, Article, Research Support, Non-U.S. Gov’t, Journal of Organic Chemistry called Synthesis of α-Trifluoromethylacrylates by Ligand-Free Palladium-Catalyzed Mizoroki-Heck Reaction, Author is Xiao, Pan; Schlinquer, Claire; Pannecoucke, Xavier; Bouillon, Jean-Philippe; Couve-Bonnaire, Samuel, the main research direction is fluoromethylacrylate synthesis palladium catalyzed Mizoroki Heck; coumarin fluoromethyl synthesis.Reference of 5-Iodo-2-furaldehyde.

Efficient ligand-free palladium catalyzed Mizoroki-Heck reaction allowed the formation of trisubstituted α-trifluoromethylacrylates. The reaction showed good chem. tolerance and furnished moderate to excellent yields of reaction. Silver salt additive proved to be essential for the reaction. The reaction has been then applied to the formation of 3-trifluoromethyl coumarins and analogs of therapeutic agents.

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1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, RSC Advances called Synthesis of novel (benzimidazolyl)isoquinolinols and evaluation as adenosine A1 receptor tools, Author is Singh, Sameek; Cooper, Samantha L.; Glenn, Jacqueline R.; Beresford, Jessica; Percival, Lydia R.; Tyndall, Joel D. A.; Hill, Stephen J.; Kilpatrick, Laura E.; Vernall, Andrea J., which mentions a compound: 91523-50-1, SMILESS is OC(=O)C1NCCC2=C1C=CC(O)=C2, Molecular C10H11NO3, Recommanded Product: 91523-50-1.

G protein-coupled receptors (GPCRs) constitute the largest family of transmembrane receptors in eukaryotes. The adenosine A1 receptor (A1AR) is a class A GPCR that is of interest as a therapeutic target particularly in the treatment of cardiovascular disease and neuropathic pain. Increased knowledge of the role A1AR plays in mediating these pathophysiol. processes will help realize the therapeutic potential of this receptor. There is a lack of enabling tools such as selective fluorescent probes to study A1AR, therefore we designed a series of (benzimidazolyl)isoquinolinols conjugated to a fluorescent dye (31-35, 42-43). An improved procedure for the synthesis of isoquinolinols from tetrahydroisoquinolinols via oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and atm. oxygen is reported. This synthetic method offers advantages over previous metal-based methods for the preparation of isoquinolinols and isoquinolines, which are important scaffolds found in many biol. active compounds and natural products. We report the first synthesis of the (benzimidazolyl)isoquinolinol compound class, however the fluorescent conjugates were not successful as A1AR fluorescent ligands.

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1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of iodo derivatives of the furan series. 5-Iodofurfural》. Authors are Nazarova, Z. N..The article about the compound:5-Iodo-2-furaldehydecas:2689-65-8,SMILESS:IC1=CC=C(O1)C=O).Formula: C5H3IO2. Through the article, more information about this compound (cas:2689-65-8) is conveyed.

All 5-bromo or -iodo derivatives of furan lose halogen quant. on standing 48 h. in the dark in HNO3 (d. 1.4) in the presence of AgNO3, followed by heating to 50-60° until N oxide vapor appear; the method can be used for anal. of these compounds Refluxing 35 g. 5-bromofurfural with 3.5 g. KI and 180 mL. AcOH 1 h., followed by dilution with H2O gave 96% crude product, m. 124-6°, which gave 80% pure 5-iodofurfural, m. 127.5-8° (from EtOH); with HNO3 it gives vapor of iodine; oxime, decompose 167-8°; semicarbazone, decompose 199-200°. The aldehyde in 30% NaOH treated with a few drops H2O2 and kept 4 days, then acidified, gave 58.8% 5-iodofurancarboxylic acid, decompose 197-8° (from H2O). The aldehyde heated with Ac2O-AcOK at 145-50°, then boiled with a little H2O 15 min. gave 82.2% 5-iodo-2-furylacrylic acid, decompose 159-60° (from dilute dioxane). The aldehyde condensed with MeNO2 (cf. C.A. 49, 9606b) gave 86% 1-(5-iodo-2-furyl)-2-nitroethylene (I), yellow-orange, m. 112-13° (from EtOH); if the intermediately formed Na salt is filtered directly from the mixture and is carefully decomposed with AcOH after washing with Et2O and MeOH, there is formed the unstable nitro alc., orange-red oil, which after steam distillation gave 80% I, m. 112-13°. The Br analog heated with KI and NaI in AcOH 2 h. on a steam bath gave 82.6% I. Heating 2-(5-bromo-2-furyl)-1-chloro-1-nitroethylene (cf. loc. cit.) with NaI in AcOH 2 h. gave 48.2% 5-iode analog, C6H3BrCINO3, m. 109-9.5° (from EtOH), an irritant which loses iodine on heating with HNO3.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem