Category: 120570-05-0

Hewlett, William A.; De Paulis, Tomas; Mason, N. Scott; Schmidt, Dennis E.; Trivedi, Bakula L.; Zhang, Zhang-Jin; Ebert, Michael H. published the artcile< Synthesis and radiolabeling of (S)-4-amino-5-iodo-2-methoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide, the active enantiomer of [125I]iodozacopride, and re-evaluation of its 5-HT3 receptor affinity>, Name: (S)-3-Amino-1-azabicyclo[2.2.2]octane, the main research area is iodozacopride radiolabeled preparation receptor affinity; HT3 receptor affinity radiolabeled iodozacopride.

Unlabeled (S)-iodozacopride was prepared in seven steps from 4-aminosalicylic acid via alk. hydrolysis of its 4-acetamide derivative Catalytic hydrogenation of (S)-iodozacopride gave dechloro-(S)-zacopride, identical to that obtained from (S)-3-aminoquinuclidine and 4-amino-2-methoxybenzoic acid via its corresponding 1-imidazole derivative Radioiodination to produce (S)-[125]iodozacopride was accomplished by treatment of dechloro-(S)-zacopride with 5 mCi sodium 125iodide and chloramine-T in hydrochloric acid. Purification of the reaction products using an HPLC system capable of detecting chlorinated side-products revealed a mixture of 2.1 mCi (1.3 nmol) (S)-[125I]iodozacopride and (S)-zacopride (1.5 nmol). Saturation anal. of the binding of the purified (S)-[125I]iodozacopride to whole rat brain homogenates gave an estimated KD of 1.10±0.07 nM. As anticipated, this is approx. half the KD reported for binding of racemic [125I]iodozacopride, and differs from the previously reported value by an order of magnitude. Anal. of the apparent binding affinity of a 1:1 mixture of (S)-[125I]iodozacopride and (S)-zacopride suggests that the previous result may have been confounded by contamination of the product with unlabeled (S)-zacopride. Competition anal. of the displacement of (S)-[125I]iodozacopride binding by unlabeled (S)-iodozacopride and (S)-zacopride gave Ki values of 0.95 and 0.21 nM, resp.

Chemical & Pharmaceutical Bulletin 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, Name: (S)-3-Amino-1-azabicyclo[2.2.2]octane.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Reed, J. Norm published the artcile< Product subclass 13: Benzyllithium compounds and (lithiomethyl)hetarenes>, Category: quinuclidine, the main research area is review benzyllithium derivative preparation organic synthesis.

A review of the preparation of benzylithium compounds and their applications to organic synthesis.

Science of Synthesis published new progress about Alkali metal organometallic compounds Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (benzyl). 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Category: quinuclidine.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Kowalczyk, Bruce A. published the artcile< A short total synthesis of palonosetron using catalytic hydrogenation>, Synthetic Route of 120570-05-0, the main research area is total synthesis palonosetron.

The 5-HT3 receptor antagonists (I) and (II) (palonosetron) were synthesized by an efficient new route. The critical hydrogenation of imide III was carried out with either Pd/C catalyst or PtO2 catalyst.

Heterocycles published new progress about 120570-05-0. 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

Odzak, Renata; Tomic, Srdanka published the artcile< 3-Amidoquinuclidine derivatives: Synthesis of compounds and inhibition of butyrylcholinesterase>, Application of C7H14N2, the main research area is amidoquinuclidine preparation butyrylcholinesterase inhibition SAR.

The synthesis of racemic and enantiomerically pure 3-butanamidoquinuclidines ((±)-Bu, (R)-Bu and (S)-Bu), (1-3) and 3-benzamidoquinuclidines ((±)-Bz, (R)-Bz, and (S)-Bz), (4-6) is described. The N-quaternary derivatives, N-benzyl-3-butanamidoquinuclidinium bromides ((±)-BnlBu, (R)-BnlBu and (S)-BnlBu), (7-9) and N-benzyl-3-benzamidoquinuclidinium bromides ((±)-BnlBz, (R)-BnlBz and (S)-BnlBz), (10-12) were subsequently synthesized. The interaction of the four enantiomerically pure quaternary derivatives with horse serum butyrylcholinesterase (BChE) was tested. All tested compounds inhibited the enzyme. The best inhibitor of the enzyme was (S)-BnlBz with a K i = 3.7 μM. The inhibitor potency decreases in order (S)-BnlBz > (R)-BnlBz ≫ (R)-BnlBu > (S)-BnlBu.

Bioorganic Chemistry published new progress about Structure-activity relationship. 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Application of C7H14N2.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

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>, Category: quinuclidine, 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, Category: quinuclidine.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

de Paulis, Tomas; Trivedi, Bakula L.; Zhang, Zhang-Jin; Schmidt, Dennis E.; Ebert, Michael H.; Hewlett, William A. published the artcile< (S)-4-Amino-5-chloro-3-iodo-2-methoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide (TRIZAC), a high-affinity ligand for the 5-HT-3 receptor>, Application In Synthesis of 120570-05-0, the main research area is aminochloroiodomethoxyazabicyclooctylbenzamide TRIZAC serotoninergic S3 receptor.

TRIZAC is one of the most potent 5-HT-3 receptor antagonist reported to date, having 20-fold higher affinity than (S)-5-iodozacopride. This high affinity (Ki 0.05±0.01 nM) and a moderate apparent lipophilicity (log Papp 2.12) makes TRIZAC a promising ligand for studying 5-HT-3 receptors.

Bioorganic & Medicinal Chemistry Letters 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, Application In Synthesis of 120570-05-0.

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>, Computed Properties of 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, Computed Properties of 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>, Recommanded Product: (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, Recommanded Product: (S)-3-Amino-1-azabicyclo[2.2.2]octane.

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>, Quality Control 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 Chemistrypublished 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, Quality Control of 120570-05-0.

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>, Name: (S)-3-Amino-1-azabicyclo[2.2.2]octane, 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 Chemistrypublished new progress about Dipole moment. 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