Month: April 2022

HPLC of Formula: 17739-45-6. 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: 2-(2-Bromoethoxy)tetrahydro-2H-pyran, is researched, Molecular C7H13BrO2, CAS is 17739-45-6, about Development of high-affinity fluorinated ligands for cannabinoid subtype 2 receptor, and in vitro evaluation of a radioactive tracer for imaging. Author is Modemann, Daniel J.; Mahardhika, Andhika B.; Yamoune, Sabrina; Kreyenschmidt, Anne-Katrin; Maass, Frederike; Kremers, Sarah; Breunig, Christian; Sahlmann, Carsten-Oliver; Bucerius, Jan; Stalke, Dietmar; Wiltfang, Jens; Bouter, Yvonne; Mueller, Christa E.; Bouter, Caroline; Meller, Birgit.

The development of neurodegenerative diseases is associated with cerebral inflammation, which activates resident immune cells of the central nervous system (CNS), namely microglial cells that show an up-regulation of the cannabinoid subtype 2 receptor (CB2R) expression. Therefore our work aimed to design and synthesize a radiotracer for the detection of CB2R expression by positron emission tomog. (PET) allowing an early diagnosis of neurodegenerative diseases. For the development of such a PET tracer, N-alkyl-substituted indole-3-yl-tetramethylcyclopropylketones served as lead structures due to their high CB2R potency and selectivity, allowing radiolabeling on the N-alkyl chain. To this end, eight novel fluorinated N-alkyl-indole-3-yl-tetramethylcyclopropylketones were synthesized, investigated in radioligand binding studies, and structure-activity relationships were evaluated. The most promising candidate was (1-(4-fluoropropyl)-1H-indole-3-yl)(2,2,3,3-tetramethyl-cyclopropyl)methanone (Ki: 7.88 nM at the CB2R, 3430 nM at cannabinoid subtype 1 receptor (CB1R)). A precursor was synthesized, radiofluorinated with no-carrier-added [18F]F- by nucleophilic substitution of a tosyl group, and the resulting PET ligand was purified, all being performed on a fully automated synthesis module. The tracer was produced in 34 ± 6% radiochem. yield within 2 h and with molar activities of up to 1500 GBq/μmol. A first preclin. evaluation was carried out including determination of logP, metabolic stability by liver microsomes, and autoradiog. The novel PET tracer for imaging CB2R showed promising results warranting subsequent clin. evaluation.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – 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: 39977-42-9, is researched, SMILESS is O=C(OC)C1=NC=C(CO)C=C1, Molecular C8H9NO3Journal, Tetrahedron Letters called Simultaneous dehalogenation and hydrogenation reduction of halogen-heteroaromatic aldehydes, Author is Chen, Xi-Bo; Hu, Qiu-Peng; Yuan, Qian-Jia; Ding, Wei; Ren, Jiangmeng; Zeng, Bu-Bing, the main research direction is halogenated heteroaromatic aldehyde dehalogenation hydrogenation; heteroaralkyl alc preparation.Quality Control of Methyl 5-(hydroxymethyl)picolinate.

Treatment of halo-heteroaromatic aldehydes with a catalytic amount of PdCl2 under atm. pressure of H2 in base medium (NaOAc) leads to the corresponding dehalogenated primary alcs. The reaction system was especially effective for heteroaromatic compounds bearing aldehyde groups and halides (Br or Cl).

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 21778-81-4, is researched, Molecular C10H9NO2, about Highly Enantioselective Synthesis of Tetrahydro-β-Carbolines and Tetrahydro-γ-Carbolines Via Pd-Catalyzed Intramolecular Allylic Alkylation, the main research direction is beta gamma carboline enantioselective regioselective preparation; pyrrolopyridine enantioselective regioselective preparation; indolylmethylamino butenol carbonate preparation enantioselective regioselective cyclocondensation; palladium catalyzed asym intramol allylic alkylation indolylmethylamino butenol carbonate; mol crystal structure beta carboline camphorsulfonamide.Synthetic Route of C10H9NO2.

(2-Indolylmethylamino) or (3-indolylmethylamino)butadienyl carbonates such as I and a (pyrrolylmethylamino)butadienyl carbonate undergo enantioselective intramol. allylic alkylation reactions in the presence of tris(dibenzylideneacetone)palladium and nonracemic (diphenylphosphinobenzoyl)diamines such as II to yield nonracemic tetrahydro-β-carbolines, tetrahydro-γ-carbolines, and a pyrrolopyridine such as III (R = PhCH2) and IV (R = PhCH2) in 82-97% ee. (indolylmethylamino)butadienyl or (pyrrolylmethylamino)butadienyl carbonates such as I are prepared from indolecarboxaldehydes by imine formation and reduction, alkylation of the amines with bromobutenoate esters (or a bromobutenal), reduction of the ester or aldehyde with diisobutylaluminum hydride, and acylation with Me chlorocarbonate. A variety of ligands for the cyclocondensation are tried; diphenylphosphinobenzamides such as II give carbolines with the highest regioselectivities and enantioselectivities of the ligands tried. (indolylmethylamino)butadienyl carbonates substituted either on the indole or the butenyl moieties yield carbolines with similar enantio- and regioselectivities. An (E)-3-indolylmethylaminobutenol carbonate undergoes regio- and enantioselective allylic alkylation to yield a γ-carboline in 90% yield and 93% yield, while intramol. allylic alkylation of the corresponding (Z)-3-indolylmethylaminobutenol carbonate yields the opposite enantiomer in 65% yield and in 5% ee. The absolute configuration of III (R = PhCH2) is determined by X-ray crystallog. anal. of a β-carboline (-)-camphorsulfonamide derived from its enantiomer [the minor stereoisomer generated in the allylic alkylation which yields III (R = PhCH2)].

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Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Formula: C10H9NO2. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 5-Methoxy-1H-indole-2-carbaldehyde, is researched, Molecular C10H9NO2, CAS is 21778-81-4, about Copper-Catalyzed Annulation of 2-Formylazoles with o-Aminoiodoarenes. Author is Reeves, Jonathan T.; Fandrick, Daniel R.; Tan, Zhulin; Song, Jinhua J.; Lee, Heewon; Yee, Nathan K.; Senanayake, Chris H..

In the presence of catalytic CuI and sparteine, 2-formylpyrroles can be annulated with o-aminoiodoarenes to give substituted pyrrolo[1,2-a]quinoxalines and related heterocycles. The reaction also works for annulation of 2-formylindoles, 2-formylimidazole, 2-formylbenzimidazole, and a 3-formylpyrazole.

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Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

COA of Formula: C4H9ClFN. 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: (R)-(-)-3-Fluoropyrrolidine Hydrochloride, is researched, Molecular C4H9ClFN, CAS is 136725-55-8, about Urea Derivatives of 2-Aryl-benzothiazol-5-amines: A New Class of Potential Drugs for Human African Trypanosomiasis. Author is Patrick, Donald A.; Gillespie, J. Robert; McQueen, Joshua; Hulverson, Matthew A.; Ranade, Ranae M.; Creason, Sharon A.; Herbst, Zackary M.; Gelb, Michael H.; Buckner, Frederick S.; Tidwell, Richard R..

A previous publication from this lab explored the antitrypanosomal activities of novel derivatives of 2-(2-benzamido)ethyl-4-phenylthiazole, which had been identified as a hit against Trypanosoma brucei, the causative agent of human African trypanosomiasis. While a number of these compounds, particularly the urea analogs, were quite potent, these mols. as a whole exhibited poor metabolic stability. The present work describes the synthesis of 65 new analogs arising from medicinal chem. optimization at different sites on the mol. The most promising compounds were the urea derivatives of 2-aryl-benzothiazol-5-amines. One such analog, (S)-2-(3,4-difluorophenyl)-5-(3-fluoro-N-pyrrolidylamido)benzothiazole (I) was chosen for in vivo efficacy studies based upon in vitro activity, metabolic stability, and brain penetration. This compound attained 5/5 cures in murine models of both early and late stage human African trypanosomiasis, representing a new lead for the development of drugs to combat this neglected disease.

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Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Related Products of 21778-81-4. 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-Methoxy-1H-indole-2-carbaldehyde, is researched, Molecular C10H9NO2, CAS is 21778-81-4, about Acid Catalyzed Synthesis of Spiroindolone Scaffolds by Iso-Pictet-Spengler Spirocyclization and Evaluation of their Antibacterial Activity. Author is Dawange, Monali A.; Urmode, Tukaram D.; Khan, Ayesha; Kusurkar, Radhika S..

Acetic acid catalyzed synthesis of new spiroindolones (tetrahydrospiro-γ-carbolines) was achieved in good yield by iso-Pictet Spengler spirocyclization of substituted isotryptamines with isatins. All the compounds were screened for antibacterial activities against S. aureus, E. coli, P. aeruginosa and S. typhi bacteria. The preliminary antibacterial study indicated that compounds bearing halo substituent showed potent inhibitory activity towards S. typhi and P. aeruginosa and moderate activities towards S. aureus and E. coli.

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Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 2-(2-Bromoethoxy)tetrahydro-2H-pyran, is researched, Molecular C7H13BrO2, CAS is 17739-45-6, about Novel 18F-Labeled Isonicotinamide-Based Radioligands for Positron Emission Tomography Imaging of Glycogen Synthase Kinase-3β, the main research direction is fluorine 18 isonicotinamide radioligand preparation PET imaging GSK3 brain; 18F-labeled; GSK-3β; PET; brain; isonicotinamide.SDS of cas: 17739-45-6.

Glycogen synthase kinase-3β (GSK-3β), a cytoplasmic serine/threonine protein kinase, is involved in several human pathologies including Alzheimer’s disease, bipolar disorder, diabetes, and cancer. Positron emission tomog. (PET) imaging of GSK-3β could aid in investigating GSK-3β levels under normal and pathol. conditions. In this study, we designed and synthesized fluorinated PET radioligands starting with recently identified isonicotinamide derivatives that showed potent affinity to GSK-3β. After extensive in vitro inhibitory activity assays and analyzing U87 cell uptake, we identified [18F]10a-d as potential tracers with good specificity and high affinity. They were then subjected to further in vivo evaluation in rodent brain comprising PET imaging and metabolism studies. The radioligands [18F]10b-d penetrated the blood-brain barrier and accumulated in GSK-3β-rich regions, including amygdala, cerebellum, and hippocampus. Also, it could be specifically blocked using the corresponding standard compounds With these results, this work sets the basis for further development of novel 18F-labeled GSK-3β PET probes.

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Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – 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: 2-(2-Bromoethoxy)tetrahydro-2H-pyran, is researched, Molecular C7H13BrO2, CAS is 17739-45-6, about New GSH-responsive amphiphilic zinc(II) phthalocyanine micelles as efficient drug carriers for combinatorial cancer therapy.Computed Properties of C7H13BrO2.

Combination therapies for the treatment of cancer have attracted wide attention. The poor selectivity and biocompatibility of photosensitizers (PS) limit the use of combination therapies in chemotherapy and photodynamic therapy (PDT) for cancer. In this work, the Gender PS (mPEG-b-PLA-S-S-ZnPC), asym. zinc(II) phthalocyanine (ZnPC) and mono-methoxy oxygen-based polyethylene glycol-polylactic acid (mPEG-b-PLA) were designed and synthesized for PDT through disulfide bond (-S-S-). The amphipathic PS could be self-assembled into a micelle in aqueous solution, and paclitaxel (PTX) was encapsulated in the core of the micelle for chemotherapy (PTX/mPEG-b-PLA-S-S-ZnPc). The PTX/mPEG-b-PLA-S-S-ZnPc micelle was spherical with a uniform diameter of about 184 nm. At the first 48 h, the release behaviors of ZnPC and PTX at 10 mmol / L GSH were 30% and 75.2%, resp. These results suggested that GSH-responsive PTX/mPEG-b-PLA-S-S-ZnPc micelle was an active ingredient in combination therapies for cancer.

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Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Electric Literature of C7H13BrO2. 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: 2-(2-Bromoethoxy)tetrahydro-2H-pyran, is researched, Molecular C7H13BrO2, CAS is 17739-45-6, about Synthesis and preclinical evaluation of [18F]PF04217903, a selective MET PET tracer. Author is Lien, Vegard Torp; Hauge, Emily; Nuruddin, Syed; Klaveness, Jo; Olberg, Dag Erlend.

The tyrosine kinase MET (hepatocyte growth factor receptor) is abnormally activated in a wide range of cancers and is often correlated with a poor prognosis. Precision medicine with positron emission tomog. (PET) can potentially aid in the assessment of tumor biochem. and heterogeneity, which can prompt the selection of the most effective therapeutic regimes. The selective MET inhibitor PF04217903 (1) formed the basis for a bioisosteric replacement to the deoxyfluorinated analog [18F]2, intended as a PET tracer for MET. [18F]2 could be synthesized with a “”hydrous fluoroethylation”” protocol in 6.3 ± 2.6% radiochem. yield and a molar activity of >50 GBq/μmol. In vitro autoradiog. indicated that [18F]2 specifically binds to MET in PC3 tumor tissue, and in vivo biodistribution in mice showed predominantly a hepatobiliary excretion along with a low retention of radiotracer in other organs.

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Pyridazine – Wikipedia,
Pyridazine | 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 Fluorine in medicinal chemistry: β-fluorination of peripheral pyrrolidines attached to acridine ligands affects their interactions with G-quadruplex DNA, published in 2011-03-07, which mentions a compound: 136725-55-8, Name is (R)-(-)-3-Fluoropyrrolidine Hydrochloride, Molecular C4H9ClFN, Related Products of 136725-55-8.

Comparative X-ray structure studies reveal that C-F bond incorporation into the peripheral pyrrolidine moieties of the G-quadruplex DNA binding ligand BSU6039 leads to a distinct pyrrolidine ring conformation, relative to the non-fluorinated analog, and with a different binding mode involving reversal of the pyrrolidinium N+-H orientation.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem