Category: quinuclidine

Hewlett, William A.; Schmidt, Dennis E.; Mason, N. Scott; Trivedi, Bakula L.; Ebert, Michael H.; De Paulis, Tomas published the artcile< Synthesis and 5-HT3 receptor binding of 2- and 3-(halo)alkoxy substituted (S)-N-(1-azabicyclo[2.2.2]oct-3-yl)-5-chlorobenzamides as potential radioligands>, Recommanded Product: (S)-3-Amino-1-azabicyclo[2.2.2]octane, the main research area is benzamide alkoxyazabicyclooctylhalo preparation 5HT3 receptor binding; receptor 5HT3 binding alkoxyazabicyclooctylhalobenzamide radioligand; azabicyclooctaneazabicyclooctane alkoxyhalobenzamido preparation 5HT3 receptor binding.

In an effort to develop selective, high-affinity radioligands for the 5-HT3 receptor, a series of homologs of 5-chloro-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide (I, R = Cl) was prepared in which individual methoxy groups were replaced by ethoxy, 2-fluoroethoxy, allyloxy, propargyloxy, or (3-iodoallyl)oxy groups. Affinities for the 5-HT3 receptor were determined by displacement of the binding of [125I]MIZAC (I, R = 125I), a selective 5-HT3 receptor antagonist radioligand, in rat brain homogenates. The 3-substituted homologs were more potent than the lead compound, I (R = Cl). The homolog having the largest 3-substituent, i.e., (E)-(S)-II (R = OCH2CH:CHI, R1 = OMe) (THIZAC), had one of the highest affinities, Ki 0.08 nM. The 2-substituted homologs were equipotent with I (R = Cl), having Ki 0.2-0.3 nM, regardless of the size of the substituent. The corresponding iodoallyl derivative, (E)-(S)-II (R = OMe, R1 = OCH2CH:CHI) (LIZAC), displayed a Ki of 0.29 nM. Saturation binding of [125I]-LIZAC gave a KD of 0.31 ± 0.04 nM and a Bmax of 2.36 ± 0.10 fmol/mg of entorhinal cortex. In vivo biodistribution of [125I]-LIZAC in the rat brain showed increased accumulation in hippocampus relative to that in cerebellum. Both the high-affinity ligands [125I]-THIZAC and [125I]-LIZAC are potentially useful radioligands for studying the 5-HT3 receptor.

Nuclear Medicine and Biology published new progress about 5-HT3 antagonists. 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

De Paulis, T.; Hewlett, W. A.; Schmidt, D. E.; Mason, N. S.; Trivedi, B. L.; Ebert, M. H. published the artcile< Synthesis and 5-HT-3 receptor binding activity of 5-[125I]iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide and its 5-halogen-2-alkoxyl homologs>, Quality Control of 120570-05-0, the main research area is benzamide derivative serotonin receptor binding structure; azabicyclooctylbenzamide serotonin receptor binding structure; iodine labeling benzamide serotonin receptor binding; PET iodine labeled benzamide serotonin receptor; SPECT iodine labeled benzamide serotonin receptor.

(S)-5-Iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide (MIZAC) was prepared from 5-iodo-2,3-dimethoxybenzoyl chloride and (S)-3-aminoquinuclidine. [125I]iodide-stannylation of its corresponding 5-tri-n-butyltin derivative gave [125I]-MIZAC at 1800 Ci/mmol. Binding of [125I]-MIZAC in rat entorhinal cortex revealed a KD of 1.37 nM. A series of racemic 2-O-alkyl derivatives of MIZAC were prepared and 5-HT-3 receptor affinities were determined by inhibition of [125I]-MIZAC binding. Optimal affinity for the receptor was obtained with small, electron-withdrawing substituents in the aromatic 5-position and with bulky substituents in the 3-position. [125I]-MIZAC is a selective radioligand useful for in vitro identification of the 5-HT-3 receptor. QSAR data suggest that potential candidates for SPECT and PET studies might be found in sterically bulky haloalkoxyl 5-chloro homologs of MIZAC.

European Journal of Medicinal Chemistry published new progress about 5-HT3 receptors Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 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

Meng, Genyi; Guo, Taijie; Ma, Tiancheng; Zhang, Jiong; Shen, Yucheng; Sharpless, Karl Barry; Dong, Jiajia published the artcile< Modular click chemistry libraries for functional screens using a diazotizing reagent>, Product Details of C7H14N2, the main research area is alkyl aryl azide triazole chemoselective preparation; fluorosulfonyl azide generation chemoselective diazotization primary amine; combinatorial generation library alkyl aryl azide cycloaddition alkyne; functional screen click chem azide generated in situ.

Alkyl and aryl azides were prepared from the corresponding primary alkyl and aryl amines by reaction with fluorosulfonyl azide generated in situ from a fluorosulfonylimidazolium triflate and sodium azide, expanding access to azides and both to the 1,2,3-triazoles derived from them and to functional screens employing them. The method allowed the preparation of a library of >1000 azides from the corresponding amines; the azide library underwent copper-catalyzed azide-alkyne cycloaddition reactions to yield a library of >1000 1,2,3-triazoles.

Nature (London, United Kingdom) published new progress about Alkyl azides Role: CMB (Combinatorial Study), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Product Details of C7H14N2.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Bozdag, Murat; Carta, Fabrizio; Vullo, Daniela; Akdemir, Atilla; Isik, Semra; Lanzi, Cecilia; Scozzafava, Andrea; Masini, Emanuela; Supuran, Claudiu T. published the artcile< Synthesis of a new series of dithiocarbamates with effective human carbonic anhydrase inhibitory activity and antiglaucoma action>, HPLC of Formula: 120570-05-0, the main research area is dithiocarbamate preparation carbonic anhydrase inhibitory activity antiglaucoma anticancer; Antiglaucoma; Carbonic anhydrase; Dithiocarbamate; Intraocular pressure.

A new series of dithiocarbamates (DTCs) was prepared from primary/secondary amines incorporating amino/hydroxyl-alkyl, mono- and bicyclic aliphatic ring systems based on the quinuclidine, piperidine, hydroxy-/carboxy-/amino-substituted piperidine, morpholine and piperazine scaffolds, and carbon disulfide. The compounds were investigated for the inhibition of four mammalian α-carbonic anhydrases (CAs, EC 4.2.1.1) of pharmacol. relevance, i.e., the human (h) hCA I, II, IX and XII, drug targets for antiglaucoma (hCA II and XII) or antitumor (hCA IX/XII) agents. The compounds were moderate or inefficient hCA I inhibitors (off-target isoform for both applications), efficiently inhibited hCA II, whereas some of them were low nanomolar/subnanomolar hCA IX/XII inhibitors. One DTC showed excellent intraocular pressure (IOP) lowering properties in an animal model of glaucoma, with a two times better efficiency compared to the clin. used sulfonamide dorzolamide.

Bioorganic & Medicinal Chemistry published new progress about Antiglaucoma agents. 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

Gong, Leyi; Parnes, Howard published the artcile< Synthesis of the 3H-labeled 4-HT3 antagonist (RS-25259-197) at high specific activity>, Safety of (S)-3-Amino-1-azabicyclo[2.2.2]octane, the main research area is RS 25259 197 tritium label preparation; tritiation RS 25259 197.

The preparation of the title compound, a selective 5-HT3 antagonist with antiemetic properties, was described. The key intermediate was 6-bromo-1,2-dihydronaphthoic acid, which was synthesized from 4-bromophenylacetic acid by Michael addition, acid-induced ring cyclization, reduction and dehydration. The compound 6-bromo-1,2-dihydronaphthoic acid was selected because it has two labeling sites to ensure high specific activity of the final product. Reduction of 6-bromo-1,2-dihydronaphthamide with carrier-free tritium gas, followed by reduction of the amide functional group with BF3-OEt2 and intramol. cyclization furnished the title compound having a specific activity of 70.4 Ci/mmol and >99% purity.

Journal of Labelled Compounds & Radiopharmaceuticals published new progress about Tritiation. 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Safety of (S)-3-Amino-1-azabicyclo[2.2.2]octane.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Kuroita, Takanobu; Sakamori, Masamitsu; Kawakita, Takeshi published the artcile< Design and synthesis of 6-chloro-3,4-dihydro-4-methyl-2H-1,4-benzoxazine-8-carboxamide derivatives as potent serotonin-3 (5-HT3) receptor antagonists>, Safety of (S)-3-Amino-1-azabicyclo[2.2.2]octane, the main research area is benzoxazinecarboxamide preparation serotonin receptor antagonist.

Several 3-substituted 5-chloro-2-methoxybenzamides I (R1 = NMe2, NH2, NMeCOMe) were synthesized and evaluated for serotonin-3 (5-HT3) receptor binding affinity. The 5-HT3 receptor antagonistic activity of zacopride, a representative 5-HT3 receptor antagonist, was unchanged by the replacement of the 4-amino substituent on the aromatic moiety by a 3-dimethylamino substituent. This finding promoted a structural modification of azasetron, another 5-HT3 receptor antagonist. Consequently, a new series of 3,4-dihydro-2H-1,4-benzoxazine-8-carboxamides II (R2 = H, Me, Et, Pr, CH2Ph, COPh, etc., R3 = Cl; R2 = Me, R3 = F, Br, Me, NO2, NH2, H) was obtained and these compounds were found to be more potent than 3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxamides. In particular, (S)-N-(1-azabicyclo[2.2.2]oct-3-yl)-6-chloro-3,4-dihydro-4-methyl-2H-1,4-benzoxazine-8-carboxamide showed a high affinity for 5-HT3 receptors (K = 0.051 nM) and especially potent antagonistic activity against the von Benzold-Jarisch reflex (ED50 = 0.089 μg/kg i.v.) in rats.

Chemical & Pharmaceutical Bulletin published new progress about 5-HT3 antagonists. 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Safety of (S)-3-Amino-1-azabicyclo[2.2.2]octane.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Glor, Ethan C.; Blau, Samuel M.; Yeon, Jeongho; Zeller, Matthias; Shiv Halasyamani, P.; Schrier, Joshua; Norquist, Alexander J. published the artcile< [R-C7H16N2][V2Te2O10] and [S-C7H16N2][V2Te2O10]; new polar templated vanadium tellurite enantiomers>, Synthetic Route of 120570-05-0, the main research area is polar vanadium tellurite enantiomer ammonioquinuclidine template hydrothermal preparation; crystal structure polar vanadium tellurite enantiomer ammonioquinuclidine template; stereoactive lone pair polar vanadium tellurite enantiomer ammonioquinuclidine template; dipole moment polar vanadium tellurite enantiomer ammonioquinuclidine template; charge distribution polar vanadium tellurite enantiomer ammonioquinuclidine template; second harmonic generation polar vanadium tellurite enantiomer ammonioquinuclidine template.

New polar vanadium tellurite enantiomers were synthesized under mild hydrothermal conditions through the use of sodium metavanadate, sodium tellurite and enantiomerically pure sources of either (R)-3-ammonioquinuclidine or (S)-3-ammonioquinuclidine. [R-C7H16N2][V2Te2O10] and [S-C7H16N2][V2Te2O10] contain [V2Te2O10]n2n- layers constructed from [(VO2)2O(TeO4)2] monomers. Steric effects associated with the H-bonding network between the [V2Te2O10]n 2n- layers and [C7H16N2]2+ result in polar structures and crystallization in the space group P21. Electron localization functions were calculated to visualize the tellurite stereoactive lone pairs. Both iterative and noniterative Hirshfeld techniques were evaluated as means to determine at. partial charges, with iterative Hirshfeld charges more accurately representing charge distributions in the reported enantiomers. These charges were used to calculate both component and net dipole moments. [R-C7H16N2][V2Te2O10] and [S-C7H16N2][V2Te2O10] exhibit dipole moments of 17.37 and 16.62 D, resp. [R-C7H16N2][V2Te2O10] and [S-C7H16N2][V2Te2O10] both display type 1 phase-matching capabilities and exhibit second harmonic generation activities of ∼50 × α-SiO2.

Journal of Solid State Chemistry published new progress about Dipole moment. 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Synthetic Route of 120570-05-0.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Lopez-Rodriguez, Maria L.; Benhamu, Bellinda; Morcillo, M. Jose; Tejada, Ignacio D.; Orensanz, Luis; Alfaro, M. Jose; Martin, M. Isabel published the artcile< Benzimidazole Derivatives. 2. Synthesis and Structure-Activity Relationships of New Azabicyclic Benzimidazole-4-carboxylic Acid Derivatives with Affinity for Serotoninergic 5-HT3 Receptors>, Application In Synthesis of 120570-05-0, the main research area is benzimidazole preparation structure serotoninergic receptor ligand; serotonin 5HT3 antagonist benzimidazole derivative structure.

A new series of azabicyclic benzimidazole-4-carboxamides and -carboxylates were synthesized and evaluated for binding affinity at serotoninergic 5-HT3 and 5-HT4 receptors in the CNS. Most of the synthesized compounds exhibited high or very high affinity for the 5-HT3 binding site and low to no significant affinity for the 5-HT4 receptor. SAR observations indicated that a halogen atom at the 6-position and a nitro group at the 7-position of the benzimidazole ring is the best substitution pattern for 5-HT3 affinity and 5-HT3/5-HT4 selectivity, as well as no substitution in this ring. Three (S)-(-)-N-(quinuclidin-3-yl)benzimidazole-4-carboxamides bound at central 5-HT3 sites with high affinity (Ki = 2.6, 0.13, and 1.7 nM, resp.) and excellent selectivity over serotonin 5-HT4 and 5-HT1A receptors (Ki > 1000-10000 nM). Furthermore, these new 5-HT3 receptor ligands were pharmacol. characterized as potent and selective 5-HT3 antagonists in the isolated guinea pig ileum (pA2 = 9.6, 9.9, and 9.1, resp.).

Journal of Medicinal Chemistry published new progress about 5-HT1A receptors Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 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

Ouach, Aziz; Pin, Frederic; Bertrand, Emilie; Vercouillie, Johnny; Gulhan, Zuhal; Mothes, Celine; Deloye, Jean-Bernard; Guilloteau, Denis; Suzenet, Franck; Chalon, Sylvie; Routier, Sylvain published the artcile< Design of α7 nicotinic acetylcholine receptor ligands using the (het)Aryl-1,2,3-triazole core: Synthesis, in vitro evaluation and SAR studies>, Safety of (S)-3-Amino-1-azabicyclo[2.2.2]octane, the main research area is triazole quinuclidinyl preparation alpha7 nicotinic acetylcholine receptor ligand; Alpha 7 nicotinic acetylcholine receptors; In vitro evaluation; Quinuclidine; SAR; Triazole synthesis; Tropane.

We report here the synthesis of a large library of 1,2,3-triazole derivatives which were in vitro tested as α7 nAchR ligands. The SAR study revealed that several crucial factors are involved in the affinity of these compounds for α7 nAchR such as a (R)-quinuclidine configuration and a mono C-3 quinuclidine substitution. The triazole ring was substituted by a Ph ring bearing small OMe/CH2F groups or fluorine atom and by several heterocycles such as thiophenes, furans, benzothiophenes, or benzofurans. Among the 30 derivatives tested, the two derivatives I and II with Ki in the nanomolar range were identified (2.3 and 3 nM resp.). They exhibited a strict selectivity toward the α4β2 nicotinic receptor (up to 1 μM) but interacted with the 5HT3 receptors with Ki around 3 nM. Synthesis, SAR studies, and a full description of the derivatives are reported.

European Journal of Medicinal Chemistry published new progress about Alkynes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Safety of (S)-3-Amino-1-azabicyclo[2.2.2]octane.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Clark, R. D.; Weinhardt, K. K.; Berger, J.; Lee, C. H.; Leung, E.; Wong, E. H. F.; Smith, W. L.; Eglen, R. M. published the artcile< N-(Quinuclidin-3-yl)-1,8-naphthalimides with 5-HT3 receptor antagonist and 5-HT4 receptor agonist properties>, Computed Properties of 120570-05-0, the main research area is quinuclidinylnaphthalimide 5HT receptor antagonist agonist; naphthalimide quinuclidinyl.

The enantiomers of N-(quinuclidin-3-yl)-4-amino-3-chloro-1,8-naphthalimide (I) were preparation and examined for interactions at 5-HT3 and 5-HT4 receptors. (R)-I was a potent 5-HT3 receptor antagonist while (S)-I was a 5-HT4 receptor agonist with reduced 5-HT3 receptor affinity.

Bioorganic & Medicinal Chemistry Letters published new progress about 5-HT4 agonists. 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Computed Properties of 120570-05-0.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider