Month: April 2022

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 5-Amino-2-fluoropyridine, is researched, Molecular C5H5FN2, CAS is 1827-27-6, about Utility of MetaSite in improving metabolic stability of the neutral indomethacin amide derivative and selective cyclooxygenase-2 inhibitor 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-N-phenethyl-acetamide, the main research direction is NSAID indomethacin amide derivative indolacetamide preparation pharmacokinetics modeling.COA of Formula: C5H5FN2.

Prediction of the metabolic sites for new compounds, synthesized or virtual, is important in the rational design of compounds with increased resistance to metabolism The aim of the present investigation was to use rational design together with MetaSite, an in silico tool for predicting metabolic soft spots, to synthesize compounds that retain their pharmacol. effects but are metabolically more stable in the presence of cytochrome P 450 enzymes. The model compound for these studies was the phenethyl amide (1) derivative of the nonsteroidal anti-inflammatory drug (NSAID) indomethacin. Unlike the parent NSAID, 1 is a potent and selective cyclooxygenase-2 (COX-2) inhibitor and nonulcerogenic anti-inflammatory agent in the rat. This pharmacol. benefit is offset by the finding that 1 is very unstable in rat and human microsomes because of extensive P 4503 A4/2D6-mediated metabolism on the phenethyl group, exptl. observations that were accurately predicted by MetaSite. The information was used to design analogs with polar (glycinyl) and/or electron-deficient (fluorophenyl, fluoropyridinyl) amide substituents to reduce metabolism in 1. MetaSite correctly predicted the metabolic shift from oxidation on the amide substituent to O-demethylation for these compounds, whereas rat and human microsomal stability studies and pharmacokinetic assessments in the rat confirmed that the design tactics for improving pharmacokinetic attributes of 1 had worked in our favor. In addition, the fluorophenyl and pyridinyl amide derivatives retained the potent and selective COX-2 inhibition demonstrated with 1. Overall, the predictions from MetaSite gave useful information leading to the design of new compounds with improved metabolic properties.

From this literature《Utility of MetaSite in improving metabolic stability of the neutral indomethacin amide derivative and selective cyclooxygenase-2 inhibitor 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-N-phenethyl-acetamide》,we know some information about this compound(1827-27-6)COA of Formula: C5H5FN2, but this is not all information, there are many literatures related to this compound(1827-27-6).

Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Name: Ethyl oxazole-5-carboxylate. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: Ethyl oxazole-5-carboxylate, is researched, Molecular C6H7NO3, CAS is 118994-89-1, about Practical preparation of challenging amides from non-nucleophilic amines and esters under flow conditions. Author is Vrijdag, Johannes L.; Delgado, Francisca; Alonso, Nerea; De Borggraeve, Wim M.; Perez-Macias, Natalia; Alcazar, Jesus.

A fast and efficient protocol for the formation of amides from low nucleophilic amines and esters in flow is described. Products were obtained in good to excellent yields and with the advantage of simultaneous mixing of all reagents at once, avoiding steps for intermediate formation. The protocol is also suitable to be combined with ester synthesis, giving amides in-line from haloarenes.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Safety of 4-Aminopyrimidine. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 4-Aminopyrimidine, is researched, Molecular C4H5N3, CAS is 591-54-8, about Nanoscale, automated, high throughput synthesis and screening for the accelerated discovery of protein modifiers. Author is Gao, Kai; Shaabani, Shabnam; Xu, Ruixue; Zarganes-Tzitzikas, Tryfon; Gao, Li; Ahmadianmoghaddam, Maryam; Groves, Matthew R.; Doemling, Alexander.

Hit finding in early drug discovery is often based on high throughput screening (HTS) of existing and historical compound libraries, which can limit chem. diversity, is time-consuming, very costly, and environmentally not sustainable. On-the-fly compound synthesis and in situ screening in a highly miniaturized and automated format has the potential to greatly reduce the medicinal chem. environmental footprint. Here, acoustic dispensing technol. has been used to synthesize a library in a 1536 well format based on the Groebke-Blackburn-Bienayme’ reaction (GBB-3CR) on a nanomole scale. The unpurified library was screened by differential scanning fluorimetry (DSF) and cross-validated using microscale thermophoresis (MST) against the oncogenic protein-protein interaction menin-MLL. Several GBB reaction products were found as μM menin binder, and the structural basis of the interactions with menin was elucidated by co-crystal structure anal. Miniaturization and automation of the organic synthesis and screening process can lead to an acceleration in the early drug discovery process, which is an alternative to classical HTS and a step towards the paradigm of continuous manufacturing

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: Ethyl oxazole-5-carboxylate( cas:118994-89-1 ) is researched.Computed Properties of C6H7NO3.Sagud, Ivana; Bozic, Simona; Marinic, Zeljko; Sindler-Kulyk, Marija published the article 《Photochemical approach to functionalized benzobicyclo[3.2.1]octene structures via fused oxazoline derivatives from 4- and 5-(o-vinylstyryl)oxazoles》 about this compound( cas:118994-89-1 ) in Beilstein Journal of Organic Chemistry. Keywords: benzobicyclooctenone preparation; fused oxazoline benzobicyclooctadiene preparation ring opening; cis trans vinylstyryl oxazole preparation intramol photocycloaddition diastereoselective; bicyclo[3.2.1]octane; intramolecular photocycloaddition; oxazole; styryl; vinyl. Let’s learn more about this compound (cas:118994-89-1).

A new photochem. approach for the preparation of functionalized benzobicyclo[3.2.1]octenones was described via fused oxazoline derivatives prepared from 4- and 5-(2-vinylstyryl)oxazoles. Novel cis/trans 4- and 5-(2-vinylstyryl)oxazoles were synthesized by Wittig reactions of o-xylelenebis(triphenylphosphoniumbromide) and formaldehyde with 4- and 5-oxazolecarbaldehydes resp. Trans-5-(2-vinylstyryl)oxazole was also prepared by the van Leusen reaction of trans-3-(2-vinylphenyl)acrylaldehyde which was prepared from o-vinylbenzaldehyde and (formylmethylene)triphenylphosphorane. The photochem. intramol. cycloaddition of cis/trans isomers of 4- and 5-(2-vinylstyryl)oxazoles afforded diverse fused oxazoline-benzobicyclo[3.2.1]octadienes I [stereo = R or S] and II which were relatively unstable. These fused oxazoline-benzobicyclo[3.2.1]octadienes underwent oxazoline ring opening spontaneously or on silica gel followed by formation of benzobicyclo[3.2.1]octenone derivatives III [X = O, stereo = R or S; X = NH, stereo = S]. Small quantity of electrocyclization product 4-(1,2-Dihydronaphthalen-2-yl)oxazole was also isolated along with desired photocycloaddition products on irradiation of 4-(2-vinylstyryl)oxazole.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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 Spectrum of antiviral activity of 4-aminopyrimidine N-oxides against a broad panel of tick-borne encephalitis virus strains, published in 2020-02-29, which mentions a compound: 591-54-8, Name is 4-Aminopyrimidine, Molecular C4H5N3, COA of Formula: C4H5N3.

Tick-borne encephalitis is an important human arbovirus neuroinfection spread across the Northern Eurasia. Inhibitors of tick-borne encephalitis virus (TBEV) strain Absettarov, presumably targeting E protein n-octyl-β-D-glucoside (β-OG) pocket, were reported earlier. In this work, these inhibitors were tested in vitro against seven strains representing three main TBEV subtypes. The most potent compound, 2-[(2-methyl-1-oxido-5,6,7,8-tetrahydroquinazolin-4-yl)amino]-phenol, showed EC50 values lower than 22 μM against all the tested strains. Nevertheless, EC50 values for virus samples of certain strains demonstrated a substantial variation, which appeared to be consistent with the presence of E protein not only in infectious virions, but also in non-infectious and immature virus particles, protein aggregates, and membrane complexes.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – 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 Nuclear Spin Hyperpolarization of NH2- and CH3-Substituted Pyridine and Pyrimidine Moieties by SABRE, published in 2020-10-01, which mentions a compound: 591-54-8, mainly applied to pyridine pyrimidine nuclear spin hyperpolarization SABRE; NMR spectroscopy; SABRE; hyperpolarization; para-hydrogen; substituent effects, Recommanded Product: 591-54-8.

Hyperpolarization of N-heterocycles with signal amplification by reversible exchange (SABRE) induces NMR sensitivity gains for biol. mols. Substitutions with functional groups, in particular in the ortho-position of the heterocycle, however, result in low polarization using a typical Ir catalyst with a bis-mesityl N-heterocyclic carbene ligand for SABRE, presumably due to steric hindrance. With the addition of allylamine or acetonitrile as coligands to the precatalyst chloro(1,5-cyclooctadiene)[4,5-dimethyl-1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene] iridium, the 1H signal enhancement increased in several substrates with ortho NH2 substitutions. For example, for a proton in 2,4-diaminopyrimidine, the enhancement factors increased from -7±1 to -210±20 with allylamine or to -160±10 with acetonitrile. CH3 substituted mols. yielded maximum signal enhancements of -25±7 with acetonitrile addition, which is considerably less than the corresponding NH2 substituted mols., despite exhibiting similar steric size. With the more electron-donating NH2 substitution resulting in greater enhancement, it is concluded that steric hindrance is not the only dominant factor in determining the polarizability of the CH3 substituted compounds The addition of allylamine increased the signal enhancement for the 290 Da trimethoprim, a mol. with a 2,4-diaminopyrimidine moiety serving as an antibacterial agent, to -70.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of C4H4BrN3O2. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 4-Bromo-1-methyl-2-nitro-1H-imidazole, is researched, Molecular C4H4BrN3O2, CAS is 121816-79-3, about Preparation and reactions of bromo-2-nitro- and bromo-2-aminoimidazoles.

Treatment of 1-methyl-2-nitroimidazole with Br in H2O resulted in rapid dibromination to 4,5-dibromo-1-methyl-2-nitroimidazole. In dioxane, the bromination was slower, but could be controlled to give 4-bromo-1-methyl-2-nitroimidazole (I) and 5-bromo-1-methyl-2-nitroimidazole (II) in a 4:1 ratio. In an attempt to displace the Br, I and II were treated with cysteamine hydrochloride and in each case the nitro group was displaced: I gave only 2-[(2-aminoethyl)thio]-4-bromo-1-methylimidazole, while II gave 2-[(2-aminoethyl)thio]-5-bromo-1-methylimidazole and 2,5-bis[2-(aminoethyl)thio]-1-methylimidazole (III). III may originate from an initial displacement of Br giving 5-[(2-aminoethyl)thio]-1-methyl-2-nitroimidazole, although this could not be observed due to a rapid further displacement of its nitro group. I and II were reduced to their corresponding amines with Zn/HCl and, when refluxed in H2O in the presence or absence of cysteamine hydrochloride, both underwent protodebromination yielding 2-amino-2-methylimidazole. In D2O, 2-amino-4-bromo-1-methylimidazole was converted into 2-amino-4-deuterio-1-methylimidazole. Bromination of 2-amino-1-methylimidazole in H2O resulted in the formation of cis- and trans-2-amino-4,5-dihydro-4,5-dihydroxyimidazolium ions.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Product Details of 118994-89-1. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: Ethyl oxazole-5-carboxylate, is researched, Molecular C6H7NO3, CAS is 118994-89-1, about Light-Promoted Copper-Catalyzed Enantioselective Alkylation of Azoles.

A catalytic asym. alkylation of azoles with secondary 1-arylalkyl bromides through direct C-H functionalization is reported. Under blue-light photoexcitation, a copper(I)/carbazole-based bisoxazoline (CbzBox) catalytic system exhibits good reactivity and high stereoselectivity, thus offering an efficient strategy for the construction of chiral alkyl azoles. These reactions proceed at low temperature and are compatible with a wide range of azoles.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Wu, Peng; Bjoern-Yoshimoto, Walden E.; Staudt, Markus; Jensen, Anders A.; Bunch, Lennart researched the compound: 4-Aminopyrimidine( cas:591-54-8 ).Reference of 4-Aminopyrimidine.They published the article 《Identification and Structure-Activity Relationship Study of Imidazo[1,2-a]pyridine-3-amines as First Selective Inhibitors of Excitatory Amino Acid Transporter Subtype 3 (EAAT3)》 about this compound( cas:591-54-8 ) in ACS Chemical Neuroscience. Keywords: imidazopyridineamine preparation inhibitor excitatory amino acid transporter subtype EAAT3; EAAT3; EAAT3 inhibitors; Glutamate; excitatory amino acid transporter. We’ll tell you more about this compound (cas:591-54-8).

Screening of a library of 49,087 compounds at the excitatory amino acid transporter subtype 3 (EAAT3) led to the identification of 2-(furan-2-yl)-8-methyl-N-(o-tolyl)imidazo[1,2-a]pyridin-3-amine which showed a >20-fold preference for inhibition of EAAT3 (IC50 = 13 μM) over EAAT1,2,4 (EAAT1: IC50 ∼ 250 μM; EAAT2,4: IC50 > 250 μM). A small lipophilic substituent (Me or bromine) at the 7- and/or 8-position was essential for activity. Furthermore, the substitution pattern of the o-tolyl group (compound I) and the chem. nature of the substituent in the 2-position of tert-Bu 3-(8-bromo-7-methyl-3-(o-tolylamino)imidazo[1,2-a]pyridin-2-yl)azetidine-1-carboxylate are essential for the selectivity toward EAAT3 over EAAT1,2. The most prominent analogs to come out of this study are 2-(furan-2-yl)-8-methyl-N-(o-tolyl)imidazo[1,2-a]pyridin-3-amine and 8-Bromo-2-(furan-2-yl)-N-(o-tolyl)imidazo[1,2-a]pyridin-3-amine that display ∼35-fold selectivity for EAAT3 (IC50 = 7.2 μM) over EAAT1,2,4 (IC50 ∼ 250 μM).

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Lassalas, Pierrik; Marsais, Francis; Hoarau, Christophe researched the compound: Ethyl oxazole-5-carboxylate( cas:118994-89-1 ).Product Details of 118994-89-1.They published the article 《DMAP-catalyzed Regel-type direct C-2 (hetero)aroylation of oxazoles and thiazoles derivatives with acid chlorides》 about this compound( cas:118994-89-1 ) in Synlett. Keywords: aroyl substituted oxazole thiazole preparation; oxazole thiazole acyl chloride aroylation DMAP catalyst. We’ll tell you more about this compound (cas:118994-89-1).

A Regel-type transition-metal-free direct C-2 aroylation of (benzo)oxazoles, (benzo)thiazoles and 1,3,4-oxadiazoles with acid chlorides catalyzed by N,N-dimethyl-4-aminopyridine (DMAP) is described. This methodol. is effective with several aroyl and heteroaroyl chlorides affording the corresponding 2-ketoazoles in moderate to excellent yields.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem