Burgi, Justus J’s team published research in ACS Chemical Neuroscience in 2014-05-21 | 120570-05-0

ACS Chemical Neuroscience published new progress about Allosterism. 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Reference of 120570-05-0.

Burgi, Justus J.; Awale, Mahendra; Boss, Silvan D.; Schaer, Tifany; Marger, Fabrice; Viveros-Paredes, Juan M.; Bertrand, Sonia; Gertsch, Jurg; Bertrand, Daniel; Reymond, Jean-Louis published the artcile< Discovery of 3-benzylamino quinuclidones as potent positive allosteric modulators of the α3β2 nicotinic acetylcholine receptor by a chemical space walk in ChEMBL>, Reference of 120570-05-0, the main research area is pos allosteric modulator benzylaminoquinuclidone alpha3beta2 nicotinic receptor ChEMBL database; benzylaminoquinuclidone preparation nicotinic receptor PAM drug discovery.

While a plethora of ligands are known for the well studied α7 and α4β2 nicotinic acetylcholine receptor (nAChR), only very few ligands address the related α3β2 nAChR expressed in the central nervous system and at the neuromuscular junction. Starting with the public database ChEMBL organized in the chem. space of Mol. Quantum Numbers (MQN, a series of 42 integer value descriptors of mol. structure), a visual survey of nearest neighbors of the α7 nAChR partial agonist N-(3R)-1-azabicyclo[2.2.2]oct-3-yl-4-chlorobenzamide (PNU-282,987) pointed to N-(2-halobenzyl)-3-aminoquinuclidines as possible nAChR modulators. This simple “”chem. space walk”” was performed using a web-browser available at www.gdb.unibe.ch. Electrophysiol. recordings revealed that these ligands represent a new and to date most potent class of pos. allosteric modulators (PAMs) of the α3β2 nAChR, which also exert significant effects in vivo. The present discovery highlights the value of surveying chem. space neighbors of known drugs within public databases to uncover new pharmacol.

ACS Chemical Neuroscience published new progress about Allosterism. 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Reference of 120570-05-0.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

 

Dash, Jyotirmayee’s team published research in Chemistry – A European Journal in 2012 | 120570-05-0

Chemistry – A European Journal published new progress about DNA Role: BSU (Biological Study, Unclassified), BIOL (Biological Study) (binding). 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Computed Properties of 120570-05-0.

Dash, Jyotirmayee; Nath Das, Rabindra; Hegde, Nagaratna; Pantos, G. Dan; Shirude, Pravin S.; Balasubramanian, Shankar published the artcile< Synthesis of Bis-indole Carboxamides as G-Quadruplex Stabilizing and Inducing Ligands>, Computed Properties of 120570-05-0, the main research area is bisindolecarboxamide preparation G quadruplex stabilizing inducing ligand structure activity.

The design and synthesis of a series of bis-indole carboxamides with varying amine containing side chains as G-quadruplex DNA stabilizing small mols. are reported. For example, reacting amines R4NH2 [R4 = Me2N(CH2)3, pyrrolidino, 1-methyl-2-pyrrolidinyl, etc.] with bisindole diacid I (R = OH), which was prepared in 3 steps from 1,3-diethynylbenzene and Me 4-amino-3-iodobenzoate, gave carboxamides I (R = NHR4) in good yield. Their interactions with quadruplexes have been evaluated by means of Foerster resonance energy transfer (FRET) melting anal., UV/Vis spectroscopy, CD spectroscopy and mol. modeling studies. FRET anal. indicates that these ligands exhibit significant selectivity for quadruplex over duplex DNA, and the position of the carboxamide side chains is of paramount importance in G-quadruplex stabilization. UV/Vis titration studies reveal that bis-indole ligands bind tightly to quadruplexes and show a three- to five-fold preference for c-kit2 over h-telo quadruplex DNA. CD studies revealed that bis-indole carboxamide with a central pyridine ring induces the formation of a single, antiparallel conformation of the h-telo quadruplex in the presence and absence of added salt. The chirality of h-telo quadruplex was transferred to the achiral ligand (induced CD) and the formation of a preferred atropisomer was observed

Chemistry – A European Journal published new progress about DNA Role: BSU (Biological Study, Unclassified), BIOL (Biological Study) (binding). 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

 

Masjedizadeh, Mohammad R’s team published research in Journal of Labelled Compounds and Radiopharmaceuticals in 1993-08-31 | 120570-05-0

Journal of Labelled Compounds and Radiopharmaceuticals published new progress about 120570-05-0. 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Quality Control of 120570-05-0.

Masjedizadeh, Mohammad R.; Parnes, Howard published the artcile< Synthesis of the serotonin ligands, RS-56532-14C and RS-66331-14C from a common labeled intermediate>, Quality Control of 120570-05-0, the main research area is carbon labeled serotonin ligand; RS66331 carbon labeled; RS56532 carbon labeled; naphthalic anhydride intermediate labeled serotonin ligand.

Two approaches towards the synthesis of 3-chloro-4-amino-1,8-naphthalic anhydride-[14C] (I), which served as the common intermediate in the preparation of the two little compounds (II and III, resp.), are described. Although nucleophilic incorporation of the label via KCN was superior to an electrophilic sequence using CO2, the latter approach was adopted since the nitrile could not be hydrolyzed to the desired acid. The specific activities of RS-56532-14C and RS-66331-14C were 56.8 mCi/mmol and 53.7 mCi/mmol, resp.

Journal of Labelled Compounds and Radiopharmaceuticals published new progress about 120570-05-0. 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

 

Youssefyeh, R D’s team published research in Journal of Medicinal Chemistry in 1992-03-06 | 120570-05-0

Journal of Medicinal Chemistry published new progress about 5-HT antagonists. 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Reference of 120570-05-0.

Youssefyeh, R. D.; Campbell, H. F.; Klein, S.; Airey, J. E.; Darkes, P.; Powers, M.; Schnapper, M.; Neuenschwander, K.; Fitzpatrick, L. R. published the artcile< Development of high-affinity 5-HT3 receptor antagonists. 1. Initial structure-activity relationship of novel benzamides>, Reference of 120570-05-0, the main research area is benzamide quinuclidinyl serotonin receptor antagonist; antiemetic quinuclidinyl benzamide.

Novel benzamides, e.g. I (X = H, Cl, Br, n = 1; X = Cl, n = 2), II (R = Me, Me2CHCH2, CH2:CHCHMe, MeCOCHMe), and S-III which are orally active, highly potent, specific antagonists of serotonin 5-HT3 receptors were prepared and the structure-activity relationships that led to these novel structures with improved potency in selectivity are described. (S)-III was identified and selected for further evaluation as a 5-HT3 receptor antagonist. Compared with 5-HT3 antagonists such as GR 38032F, BRL 43694, and metoclopramide, (S)-III was most active in (a) inhibiting binding to 5-HT3 receptor binding sites in rat entorhinal cortex with a Ki value of 0.19 nM and (b) blocking cisplatin-induced emesis in the ferret with an ED50 value determined to be 9 mg/kg, i.d.

Journal of Medicinal Chemistry published new progress about 5-HT antagonists. 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Reference of 120570-05-0.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

 

Bodnar, Alice L’s team published research in Journal of Medicinal Chemistry in 2005-02-24 | 120570-05-0

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.

Bodnar, Alice L.; Cortes-Burgos, Luz A.; Cook, Karen K.; Dinh, Dac M.; Groppi, Vincent E.; Hajos, Mihaly; Higdon, Nicole R.; Hoffmann, William E.; Hurst, Raymond S.; Myers, Jason K.; Rogers, Bruce N.; Wall, Theron M.; Wolfe, Mark L.; Wong, Erik published the artcile< Discovery and Structure-Activity Relationship of Quinuclidine Benzamides as Agonists of α7 Nicotinic Acetylcholine Receptors>, Quality Control of 120570-05-0, the main research area is quinuclidine benzamide library preparation nicotinic receptor agonist.

A library of benzamides was tested for α7 nicotinic acetylcholine receptor (nAChR) agonist activity using a chimeric receptor in a functional, cell-based, high-throughput assay. From this library, quinuclidine benzamides were found to have α7 nAChR agonist activity. The SAR diverged from the activity of this compound class verses the 5-HT3 receptor, a structural homolog of the α7 nAChR. PNU-282987 (I), the most potent compound from this series, was also shown to open native α7 nAChRs in cultured rat neurons and to reverse an amphetamine-induced gating deficit in rats.

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

 

Odzak, Renata’s team published research in Croatica Chemica Acta in 2007-05-31 | 120570-05-0

Croatica Chemica Acta published new progress about Amides 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, Electric Literature of 120570-05-0.

Odzak, Renata; Primozic, Ines; Tomic, Srdanka published the artcile< 3-amidoquinuclidine derivatives: synthesis and interaction with butyrylcholinesterase>, Electric Literature of 120570-05-0, the main research area is aminoquinuclidine acid anhydride condensation; amidoquinuclidine preparation benzyl bromide alkylation; racemic enantiopure quaternary amidoquinuclidine preparation; butyrylcholinesterase inhibitor quaternary amidoquinuclidine.

Racemates as well as (R)- and (S)-enantiomers of 3-pivalamidoquinuclidine I (R = Me3C) and 3-acetamidoquinuclidine I (R = Me) were prepared Their quaternary racemic and enantiomerically pure N-benzyl derivatives II (R = Me3C, Me) were synthesized as well. I and II were tested as substrates and inhibitors of butyrylcholinesterase (BChE) from horse serum (EC 3.1.1.8). No hydrolysis was observed under the exptl. conditions applied. On the contrary, inhibition of BChE by (R)- and (S)-enantiomers of II (R = Me3C) was observed II (R = Me3C) with Ki = 41.57 μmol dm-3 was a 3-fold more potent inhibitor than the (R)-enantiomer. On the other hand, preliminary results indicated that both enantiomers of II (R = Me) may possibly be inhibitors as well as activators depending on the concentrations of benzoylcholine (BzCh) used as a substrate of BChE.

Croatica Chemica Acta published new progress about Amides 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, Electric Literature of 120570-05-0.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

 

Kuroita, Takanobu’s team published research in Chemical & Pharmaceutical Bulletin in 1996-11-30 | 120570-05-0

Chemical & Pharmaceutical Bulletin published new progress about 5-HT3 antagonists. 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, SDS of cas: 120570-05-0.

Kuroita, Takanobu; Marubayashi, Nobuhiro; Sano, Mitsuharu; Kanzaki, Kouji; Inaba, Kenichi; Kawakita, Takeshi published the artcile< Benzoxazines. II. Synthesis, conformational analysis, and structure-activity relationships of 3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide derivatives as potent and long-acting serotonin-3 (5-HT3) receptor antagonists>, SDS of cas: 120570-05-0, the main research area is serotonin antagonist antiemetic benoxazinecarboxamide analog preparation; structure activity serotonin antagonist benoxazinecarboxamide analog; conformation serotonin antagonist benoxazinecarboxamide analog preparation.

A series of 3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide derivatives was synthesized and evaluated for S3 serotonin (5-HT3) receptor antagonistic activities by means of assays of 5-HT3 receptor binding and the ability to antagonize the von Bezold-Jarisch reflex in rats. The target compounds were analogs and derivatives of (S)-N-1-azabicyclo[2.2.2]oct-3-yl-6-chloro-3,4-dihydro-4-methyl-2H-1,4-benzoxazine-8-carboxamide (I). Replacement of the 1,4-benzoxazine ring with a 1,4-benzthiazine ring or seven-membered ring (i.e., 1,5-benzoxepine or 1,5-benzthiepine) resulted in decreased affinity for 5-HT3 receptor. Introduction of substituents at the 2 position of the 1,4-benzoxazine ring increased the antagonistic activities (di-Me > Me > dihydro > phenyl). Compounds bearing a 9-methyl-9-azabicyclo[3.3.1]non-3-yl moiety as the basic part of 3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide derivatives were equipotent to those bearing 1-azabicyclo[2.2.2]oct-3-yl moiety. The 9-methyl-9-azabicyclo[3.3.1]non-3-yl moiety was confirmed to adopt a boat-chair conformation on the basis of both NMR studies and X-rays anal. In this series, endo-6-chloro-3,4-dihydro-N-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-2,2,4-trimethyl-2H-1,4-benzoxazine-8-carboxamide showed the highest affinity for 5-HT3 receptors (Ki = 0.019 nM), and a long-lasting 5-HT3 receptor antagonistic activity as evidenced by antagonism to the von Bezold-Jarisch reflex in rats. Such a long-lasting 5-HT3 receptor antagonism would be attributed to the introduction of both two Me groups at the 2 position of the benzoxazine ring and the 9-methyl-9-azabicyclo[3.3.1]non-3-yl moiety, which adopted the boat-chair conformation.

Chemical & Pharmaceutical Bulletin published new progress about 5-HT3 antagonists. 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, SDS of cas: 120570-05-0.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

 

Feng, Li’s team published research in Molecules in 2021 | 120570-05-0

Molecules published new progress about Antitumor agents. 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Category: quinuclidine.

Feng, Li; Yu, Shujia; Wang, Hai; Yang, Shengwei; Li, Xue; Dai, Hongjuan; Zhao, Liwen; Jiang, Cheng; Wang, Yazhou published the artcile< Synthesis and biological evaluation of spirocyclic chromane derivatives as a potential treatment of prostate cancer>, Category: quinuclidine, the main research area is spirocyclic chromane preparation antitumor prostate cancer; HAT inhibitors; antitumor activity; p300/CBP.

Herein, new compounds from the lead compound A-485 were designed using mol. dynamic simulations. A series of new spirocyclic chroman derivatives was prepared, characterized and proven to be a potential treatment of prostate cancer. The most potent compound I inhibited the proliferation of enzalutamide-resistant 22Rv1 cells with an IC50 value of 96 nM. Furthermore, one of diastereomers of the compound I displayed favorable overall pharmacokinetic profiles, and better tumor growth inhibition than A-485 in an in vivo xenograft model.

Molecules published new progress about Antitumor agents. 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Category: quinuclidine.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

 

Yang, Zhicai’s team published research in Bioorganic & Medicinal Chemistry Letters in 2010-11-15 | 120570-05-0

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

Yang, Zhicai; Fairfax, David J.; Maeng, Jun-Ho; Masih, Liaqat; Usyatinsky, Alexander; Hassler, Carla; Isaacson, Soshanna; Fitzpatrick, Kevin; De Orazio, Russell J.; Chen, Jianqing; Harding, James P.; Isherwood, Matthew; Dobritsa, Svetlana; Christensen, Kevin L.; Wierschke, Jonathan D.; Bliss, Brian I.; Peterson, Lisa H.; Beer, Cathy M.; Cioffi, Christopher; Lynch, Michael; Rennells, W. Martin; Richards, Justin J.; Rust, Timothy; Khmelnitsky, Yuri L.; Cohen, Marlene L.; Manning, David D. published the artcile< Discovery of 2-substituted benzoxazole carboxamides as 5-HT3 receptor antagonists>, Recommanded Product: (S)-3-Amino-1-azabicyclo[2.2.2]octane, the main research area is irritable bowel syndrome IBS serotonin receptor antagonist 5HT3 antagonist; benzoxaole derivative SAR preparation.

A new class of 2-substituted benzoxazole carboxamides are presented as potent functional 5-HT3 receptor antagonists. The chem. series possesses nanomolar in vitro activity against human 5-HT3A receptors. A chem. optimization program was conducted and identified 2-aminobenzoxazoles as orally active 5-HT3 receptor antagonists with good metabolic stability. These novel analogs possess drug-like characteristics and have potential utility for the treatment of diseases attributable to improper 5-HT3 receptor function, especially diarrhea predominant irritable bowel syndrome (IBS-D).

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

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

 

Demian, Iulia’s team published research in Journal of Chromatography in 1989-04-19 | 120570-05-0

Journal of Chromatography published new progress about Chromatographic chiral resolution. 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Related Products of 120570-05-0.

Demian, Iulia; Gripshover, David F. published the artcile< Enantiomeric purity determination of 3-aminoquinuclidine by diastereomeric derivatization and high-performance liquid chromatographic separation>, Related Products of 120570-05-0, the main research area is aminoquinuclidine enantiomer resolution HPLC; liquid chromatog aminoquinuclidine enantiomer resolution; benzoyltartaric anhydride chiral derivatization aminoquinuclidine resolution.

Four different diastereomeric derivatization methods were used for the HPLC and TLC separation of 3-aminoquinuclidine enantiomers. The chiral reagents used were S(-)-1-phenylethyl isocyanate, R(-)-1-naphthylethyl isocyanate, 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate, and the anhydrides of R,R(+)- and S,S(-)-O,O-dibenzoyltartaric acid (DBTAA). The TLC separations were carried out on silica gel plates; the HPLC used a Zorbax C8 and Zorbax Sil phase. All diastereomeric derivatives were strong UV absorbers at 254 nm. The best separation was achieved by HPLC with DBTAA, which allowed detection of the minor enantiomer down to 10-3 enantiomeric ratio.

Journal of Chromatography published new progress about Chromatographic chiral resolution. 120570-05-0 belongs to class quinuclidine, and the molecular formula is C7H14N2, Related Products of 120570-05-0.

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider