Heterocyclic Building Blocks-Quinuclidine

Kowalczyk, Bruce A.; Rohloff, John C.; Dvorak, Charles A.; Gardner, John O. published the artcile< Improved preparation of (R)- and (S)-3-aminoquinuclidine dihydrochloride>, Application In Synthesis of 120570-05-0, the main research area is quinuclidine amino hydrochloride preparation.

An improved procedure for the synthesis of either (R)- or (S)-3-aminoquinuclidine was developed. Key intermediate imine (I) was made in a one pot process using lithium oxide as the base and mol. sieves.

Synthetic Communications published new progress about 120570-05-0. 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Application In Synthesis of 120570-05-0.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Bozdag, Murat; Carta, Fabrizio; Vullo, Daniela; Isik, Semra; Al Othman, Zeid; Osman, Sameh M.; Scozzafava, Andrea; Supuran, Claudiu T. published the artcile< Dithiocarbamates with potent inhibitory activity against the Saccharomyces cerevisiae β-carbonic anhydrase>, HPLC of Formula: 120570-05-0, the main research area is dithiocarbamate inhibitor selectivity Saccharomyces beta carbonic anhydrase; Saccharomyces cerevisiae; carbonic anhydrase; dithiocarbamate; inhibitor; β-Class enzyme.

Dithiocarbamates (DTCs) prepared from primary or secondary amines, which incorporated amino/hydroxyl-alkyl, mono-/bicyclic aliphatic/heterocyclic rings based on the quinuclidine, piperidine, hydroxy-/carboxy-/amino-substituted piperidine, morpholine and piperazine scaffolds, were investigated for the inhibition of α- and β-carbonic anhydrases (CAs, EC 4.2.1.1) of pharmacol. relevance, such as the human (h) isoform hCA I and II, as well as the Saccharomyces cerevisiae β-CA, scCA. The yeast and its β-CA were shown earlier to be useful models of pathogenic fungal infections. The DTCs investigated here were medium potency hCA I inhibitors (KIs of 66.5-910 nM), were more effective as hCA II inhibitors (KIs of 8.9-107 nM) and some of them showed excellent, low nanomolar activity against the yeast enzyme, with inhibition constants ranging between 6.4 and 259 nM. The detailed structure activity relationship for inhibition of the yeast and human enzymes is discussed. Several of the investigated DTCs showed excellent selectivity ratios for inhibiting the yeast over the human cytosolic CA isoforms.

Journal of Enzyme Inhibition and Medicinal Chemistry published new progress about Carbonic anhydrase inhibitors. 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, HPLC of Formula: 120570-05-0.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Clark, R. D.; Muchowski, J. M.; Weinhardt, K. K.; Dillon, M. P.; Lee, C.-H.; Bley, K. R.; Bonhaus, D. W.; Wong, E. H. F.; Eglen, R. M. published the artcile< N-(Quinuclidin-3-yl)-2-(1-methyl-1H-indol-3-yl)-2-oxoacetamide: a high affinity 5-HT3 receptor partial agonist>, Name: (S)-3-Amino-1-azabicyclo[2.2.2]octane, the main research area is quinuclidinylindolyloxoacetamide enantiomer preparation serotoninergic receptor agonist; serotoninergic receptor partial agonist quinuclidinylindolyloxoacetamide enantiomer.

The enantiomers of the indolyl-2-oxoacetamide I were found to have 5-HT3 receptor partial agonist activity with (R)-I having higher potency than (S)-I.

Bioorganic & Medicinal Chemistry Letters published new progress about 5-HT3 agonists. 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Name: (S)-3-Amino-1-azabicyclo[2.2.2]octane.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Clark, Robin D.; Miller, Aaron B.; Berger, Jacob; Repke, David B.; Weinhardt, Klaus K.; Kowalczyk, Bruce A.; Eglen, Richard M.; Bonhaus, Douglas W.; Lee, Chi Ho published the artcile< 2-(Quinuclidin-3-yl)pyrido[4,3-b]indol-1-ones and isoquinolin-1-ones. Potent conformationally restricted 5-HT3 receptor antagonists>, Recommanded Product: (S)-3-Amino-1-azabicyclo[2.2.2]octane, the main research area is quinuclidinyl pyridoindolone isoquinolinone preparation 5HT3 antagonist; pyridoindolone quinuclidinyl preparation 5HT3 antagonist; isoquinolinone quinuclidinyl preparation 5HT3 antagonist; receptor 5HT3 antagonist quinuclidinyl pyridoindolone isoquinolinone; indolone quinuclidinylpyrido preparation 5HT3 antagonist.

Several series of N-(quinuclidin-3-yl)aryl and heteroaryl-fused pyridones were synthesized and evaluated for 5-HT3 receptor affinity. In the heteroaryl series, pyrido[4,3-b]indol-1-one I (R = Me, R1 = H) and the 4,5-alkano-bridged analogs I [RR1 = (CH2)n (n = 3, 4)] displayed high 5-HT3 receptor affinity with pKi values >9. The (3S)-quinuclidinyl isomers had >10 fold higher affinity than the (3R)-isomers. In a series of 2-(quinuclidin-3-yl)isoquinolin-1-ones, derivatives substituted with small lipophilic groups (II; R = Me, Et, OMe, Cl, R1 = H) and with 4,5-alkano-bridges [II; RR1 = (CH2)n (n = 2, 3, 4)] also displayed high affinity. In particular, the hexahydro-1H-benz[de]isoquinolinone (S,S)-37 (III) was the highest affinity 5-HT3 receptor ligand prepared (pKi 10.4). A number of the high affinity ligands were shown to be potent 5-HT3 receptor antagonists in vivo as determined by inhibition of the B-J reflex in the anesthetized rat. Again, (S,S)-37 was the most active agent tested (ID50 0.02 μg/kg i.v.), and this compound was also potent in blocking cisplatin-induced emesis in both the ferret and the dog. Computer modeling studies were performed, and previously reported 5-HT3 receptor antagonist pharmacophore models were refined to include a key lipophilic binding domain.

Journal of Medicinal Chemistry published new progress about 5-HT3 receptors Role: RCT (Reactant), RACT (Reactant or Reagent). 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Recommanded Product: (S)-3-Amino-1-azabicyclo[2.2.2]octane.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Lecoeur-Lorin, Marie; Delepee, Raphael; Morin, Philippe published the artcile< Sensitivity improvement by using contactless conductivity rather than indirect UV detection for the determination of enantiomeric purity of amines by CE>, Product Details of C7H14N2, the main research area is amine enantiomeric purity determination capillary electrophoresis contactless conductivity detection; crown compound selector amine capillary electrophoresis contactless conductivity detection; cyclodextrin derivative selector amine capillary electrophoresis contactless conductivity detection.

A capacitively coupled contactless conductivity detection (C4D) system for CE with a flexible detection cell was applied for the enantioseparation of small chiral underivatized amines using chiral crown ether or CD as chiral selector. Since these compounds are poorly UV-active, C4D was an alternative detection mode. The composition (ionic strength, pH, chiral selector) of the electrolyte was optimized to be suitable for C4D. (-)-(18-Crown-6)-2,3,11,12-tetracarboxylic acid was required as chiral selector to resolve the enantiomers of small polar amines. However, trimethyl-β-CD was suitable to sep. amines possessing hydrophobic carbon chains. The performance of C4D was compared with indirect UV detection in terms of sensitivity, repeatability and accuracy. The linearity range of C4D was very large (1.5-1600 μg/mL) compared with the indirect UV linearity range (25-400 μg/mL) and allowed the determination of the enantiomeric purity of isopinocampheylamine up to 0.25%. The CE-C4D method was fully validated by applying a novel strategy using accuracy profiles. All relative biases of the developed method were included within the ±15% limits of acceptance. C4D is a good alternative to indirect UV detection for the enantioseparation of non-UV absorbing amines since the method development is fast and easy and, the sensitivity is improved by a factor of 100 compared with that of the indirect UV mode.

Electrophoresis published new progress about Amines Role: ANT (Analyte), ANST (Analytical Study). 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Product Details of C7H14N2.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Kowalczyk, Bruce A. published the artcile< Total synthesis of RS-42358 and analogs using lateral lithiation>, Quality Control of 120570-05-0, the main research area is benzisoquinolinone preparation; RS 42358 preparation.

A short synthesis of the 5-HT3 receptor antagonist RS-42358 was developed based on the condensation of 5,6-dihydro-1H,4H-naphtho[1,8-cd]pyran-1-one (I) with S-3-aminoquinuclidine. The position 2 analogs of RS-42358 were made by condensing various primary amines with I. The key step in the synthesis of I was lateral lithiation of N,N-diethyl-5,6,7,8-tetrahydronaphthalene-1-carboxamide using BuLi in THF.

Synthesis published new progress about Lithiation. 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Quality Control of 120570-05-0.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Flippin, L. A.; Carter, D. S.; Berger, J.; Clark, R. D.; Bonhaus, D. W.; Leung, E.; Eglen, R. M. published the artcile< (R)-3-(6-chloro-1-isopropylbenzimidazole-4-carboxamido)quinuclidine: a high affinity ligand for the (R)-zacopride binding site>, Formula: C7H14N2, the main research area is serotoninergic receptor binding benzimidazolecarboxamidoquinuclidine; benzimidazolecarboxamidoquinuclidine preparation zacopride binding site affinity.

The title compound was prepared and found to be a high affinity ligand for the (R)-zacopride binding site.

Bioorganic & Medicinal Chemistry Letters published new progress about 5-HT receptors Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Formula: C7H14N2.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Austin, Wesley F.; Hubbs, Jed L.; Fuller, Nathan O.; Creaser, Steffen P.; McKee, Timothy D.; Loureiro, Robyn M. B.; Findeis, Mark A.; Tate, Barbara; Ives, Jeffrey L.; Bronk, Brian S. published the artcile< SAR investigations on a novel class of gamma-secretase modulators based on a unique scaffold>, Application In Synthesis of 120570-05-0, the main research area is SAR gamma secretase modulator scaffold black cohosh amyloid.

In this communication we present details of our analog efforts within a novel series of gamma-secretase modulating compounds Esters and carbamates were investigated as bioisosteres for a glycoside moiety present in an initial hit isolated from black cohosh extract We identified elements within each series that retain the potency and selectivity of the initial lead while improving physicochem. properties.

MedChemComm published new progress about Anti-Alzheimer agents. 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Application In Synthesis of 120570-05-0.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Mason, N. Scott; Hewlett, William A.; Ebert, Michael H.; Schmidt, Dennis E.; de Paulis, Tomas published the artcile< Labeling of (S)-des-4-amino-4-[125I]iodozacopride (DAIZAC), a high-affinity radioligand for the 5-HT-3 receptor>, Recommanded Product: (S)-3-Amino-1-azabicyclo[2.2.2]octane, the main research area is desaminoiodozacoprride iodine 125 preparation serotoninergic receptor.

We have prepared (S)-5-chloro-3-[125I]iodo-2-methoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)-benzamide ([125I]DAIZAC, [125I]-3) as a radioligand for characterization of the 5-HT-3 receptor. Preparation of the 3-tri-n-butylstannyl precursor was accomplished from the corresponding unlabeled DAIZAC by reaction with bis(tributyltin). Treatment of the precursor with 5 mCi of Na125I and chloramine-T in dilute HCl gave 2.58 ± 0.22 mCi (52%) of [125I]DAIZAC with >98% radiochem. purity and 1500 Ci/mmol specific activity. Saturation anal. of the binding of [125I]DAIZAC to rat brain homogenates showed a single binding site with a receptor d. Bmax of 0.66 ± 0.03 pmol/g and a receptor affinity KD of 0.15 ± 0.01 nM. Compared to [125I]iodozacopride, we find the 20-fold higher affinity and easy preparation of [125I]DAIZAC to be advantageous for in vitro identification of brain 5-HT-3 receptors.

Journal of Labelled Compounds & Radiopharmaceuticals published new progress about 5-HT3 receptors Role: ANT (Analyte), BSU (Biological Study, Unclassified), ANST (Analytical Study), BIOL (Biological Study). 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Recommanded Product: (S)-3-Amino-1-azabicyclo[2.2.2]octane.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Sun, Ping; Armstrong, Daniel W. published the artcile< Effective enantiomeric separations of racemic primary amines by the isopropyl carbamate-cyclofructan6 chiral stationary phase>, Electric Literature of 120570-05-0, the main research area is primary amine enantioseparation HPLC isopropyl carbamate cyclofructan6 chiral phase; amino acid enantioseparation HPLC isopropyl carbamate cyclofructan6 chiral phase; alc amino enantioseparation HPLC isopropyl carbamate cyclofructan6 chiral phase.

A new chiral stationary phase (CSP) was developed by bonding isopropyl-carbamate functionalized cyclofructan6 (IP-CF6) to the silica gel. It was evaluated by injecting 119 racemic primary amine-containing compounds This CSP showed pronounced enantioselectivity toward all types of primary amines, separating 93% of all tested compounds Baseline separation was achieved even for some simple aliphatic racemic amines that contained no other functionality. The polar organic mode is the effective mobile phase owing to higher efficiency. This new chiral stationary phase showed great potential for preparative-scale separations It is also interesting that the chiral selector, R-naphthylethyl-carbamate functionalized CF6 (RN-CF6), provides complementary selectivity for the relatively few amine analytes that did not sep. on IP-CF6. Thus between the two CSPs, 98% of attempted amine compounds were separated

Journal of Chromatography A published new progress about Amino acid esters Role: ANT (Analyte), ANST (Analytical Study). 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Electric Literature of 120570-05-0.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider