35423-17-7

Usage

Uses

Used in Organic Synthesis:
3-Quinuclidinone oxime is used as a reagent in organic synthesis for its ability to protect amino compounds and act as a precursor for various chemical reactions.
Used in Chelating Agents:
In metal ion extraction processes, 3-Quinuclidinone oxime is used as a chelating agent to bind and extract metal ions.
Used in Pharmaceutical and Medicinal Applications:
3-Quinuclidinone oxime has been studied for its potential use in pharmaceutical and medicinal applications, although further research is needed to fully understand its capabilities and safety in these areas.
Used in Chemical Research:
As a versatile chemical compound, 3-Quinuclidinone oxime is utilized in chemical research to explore its properties and potential applications in various fields.

InChI:InChI=1/C7H12N2O.ClH/c10-8-7-5-9-3-1-6(7)2-4-9;/h6,10H,1-5H2;1H/b8-7+;

Upstream product

• 1193-65-3 3-quinuclidinone hydrochloride 
• 76883-37-9 3-hydroxyimino quinuclidine hydrochloride 
• 3731-38-2 3-Quinuclidinone 
• 5470-11-1 hydroxylamine hydrochloride 

Downstream Products

• 695184-05-5 4-(6-bromo-pyridazin-3-yl)-1, 4-diazabicyclo [3.2. 2] nonane 
• 695183-61-0 4-biphenyl-4-yl-1,4-diazabicyclo[3. 2. 2]nonane fumaric acid salt 
• 677723-95-4 4-(5-phenyl-1,3,4-thiadiazol-2-yl)-1,4-diazabicyclo[3.2.2]nonane 
• 677723-97-6 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-phenyl-1,3,4-oxadiazole 
• 283-38-5 1,4-diazabicyclo[3.2.2]nonane 

Relevant academic research and scientific papers

Structure-property relationship of quinuclidinium surfactants-Towards multifunctional biologically active molecules

Motivated by diverse biological and pharmacological activity of quinuclidine and oxime compounds we have synthesized and characterized novel class of surfactants, 3-hydroxyimino quinuclidinium bromides with different alkyl chains lengths (CnQNOH; n = 12, 14 and 16). The incorporation of non conventional hydroxyimino quinuclidinium headgroup and variation in alkyl chain length affects hydrophilic-hydrophobic balance of surfactant molecule and thereby physicochemical properties important for its application. Therefore, newly synthesized surfactants were characterized by the combination of different experimental techniques: X-ray analysis, potentiometry, electrical conductivity, surface tension and dynamic light scattering measurements, as well as antimicrobial susceptibility tests. Comprehensive investigation of CnQNOH surfactants enabled insight into structure-property relationship i.e., way in which the arrangement of surfactant molecules in the crystal phase correlates with their solution behavior and biologically activity. The synthesized CnQNOH surfactants exhibited high adsorption efficiency and relatively low critical micelle concentrations. In addition, all investigated compounds showed very potent and promising activity against Gram-positive and clinically relevant Gram-negative bacterial strains compared to conventional antimicrobial agents: tetracycline and gentamicin. The overall results indicate that bicyclic headgroup with oxime moiety, which affects both hydrophilicity and hydrophobicity of CnQNOH molecule in addition to enabling hydrogen bonding, has dominant effect on crystal packing and physicochemical properties. The unique structural features of cationic surfactants with hydroxyimino quinuclidine headgroup along with diverse biological activity have made them promising structures in novel drug discovery. Obtained fundamental understanding how combination of different functionalities in a single surfactant molecule affects its physicochemical properties represents a good starting point for further biological research.

N-methylated diazabicyclo[3.2.2]nonane substituted triterpenoic acids are excellent, hyperbolic and selective inhibitors for butyrylcholinesterase

Triterpenoic acids (oleanolic, ursolic, betulinic, platanic and glycyrrhetinic acid) were acetylated and coupled with 1,3- or 1,4-diazabicyclo[3.2.2]nonanes to yield amides. Reaction of these amides with methyl iodide at the distal nitrogen of the bicyclic system gave the corresponding quaternary ammonium salts. These compounds were shown to act as excellent inhibitors of the enzyme butyrylcholinesterase (BChE) while being only weak inhibitors for acetylcholinesterase (AChE). Evaluation of the enzyme kinetics revealed these compounds to act as hyperbolic inhibitors for BChE while the results from molecular modeling gave an explanation for their selectivity between AChE and BChE.

Structure-based design of highly selective 2,4,5-trisubstituted pyrimidine CDK9 inhibitors as anti-cancer agents

Cyclin-dependent kinases (CDKs) are a family of Ser/Thr kinases involved in cell cycle and transcriptional regulation. CDK9 regulates transcriptional elongation and this unique property has made it a potential target for several diseases. Due to the conserved ATP binding site, designing selective CDK9 inhibitors has been challenging. Here we report our continued efforts in the optimization of 2,4,5-tri-substituted pyrimidine compounds as potent and selective CDK9 inhibitors. The most selective compound 30m was >100-fold selective for CDK9 over CDK1 and CDK2. These compounds showed broad anti-proliferative activities in various solid tumour cell lines and patient-derived chronic lymphocytic leukaemia (CLL) cells. Decreased phosphorylation of the carboxyl terminal domain (CTD) of RNAPII at Ser-2 and down-regulation of anti-apoptotic protein Mcl-1 were confirmed in both the ovarian cancer model A2780 and patient-derived CLL cells.

Design, synthesis, and electrophysiological evaluation of NS6740 derivatives: Exploration of the structure-activity relationship for alpha7 nicotinic acetylcholine receptor silent activation

The α7 nicotinic acetylcholine receptor (nAChR) silent agonists, able to induce receptor desensitization and promote the α7 metabotropic function, are emerging as new promising therapeutic anti-inflammatory agents. Herein, we report the structure–activity

Mechanochemical and conformational study of N-heterocyclic carbonyl-oxime transformations

New mechanochemical pathways for the transformation of six N-heterocyclic carbonyl compounds into oximes using hydroxylamine hydrochloride were explored. Reactions were performed first without any base since the heterocyclic moieties (imidazole, benzimidazole, pyridine and quinuclidine) have an intrinsic basic nitrogen atom. This green, solvent free method was suitable for all compounds (up to quantitative yields) except for N-benzyl substituted imidazole and benzimidazole-2-carbaldehyde. For the slower reacting aldehydes, reactions with liquid assisted grinding and addition of sodium hydroxide were performed as well. Conformational analysis and quantum-chemical calculations revealed steric and electronic reasons for the lower reactivity of N-benzyl substituted derivatives.

LABELLED AND UN-LABELLED METHYL-PYRROLYL-OXADIAZOLYL-DIAZABICYCLONONANE DERIVATIVES AND THEIR MEDICAL USE

The present invention relates to certain labelled or un-labelled pyrrolyl-oxadizolyl-diazabicyclononane derivatives and their medical use. Furthermore, the present invention relates to the use of said derivatives in their labelled form in diagnostic methods, in particular for in vivo receptor imaging (neuroimaging).

DIAZABICYCLONONYL OXADIAZOLE COMPOUNDS AND THEIR USE AS NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS

This invention relates to diazabicyclononyl oxadiazolyl derivatives, which are found to-be modulators of the nicotinic acetylcholine receptors. Due to their pharmacological profile the compounds of the invention may be useful for the treatment of diseases or disorders as diverse as those related to the cholinergic system of the central nervous system (CNS), the peripheral nervous system (PNS), diseases or disorders related to smooth muscle contraction, endocrine diseases or disorders, diseases or disorders related to neuro-degeneration, diseases or disorders related to inflammation, pain, and withdrawal symptoms caused by the termination of abuse of chemical substances. Ar1 represents a pyrrolyl group, optionally substituted with alkyl or halo-alkyl.

NOVEL DIAZA-BICYCLONONYL-PHENYL DERIVATIVES AND THEIR MEDICAL USE

This invention relates to novel diazabicyclononyl-phenyl derivatives and their use in the manufacture of pharmaceutical compositions. The compounds of the invention are found to be cholinergic ligands at the nicotinic acetylcholine receptors and modulator

N-OXIDES OF DIAZABICYCLONONYL PYRIMIDINE DERIVATIVES AND THEIR MEDICAL USE

This invention relates to novel N-oxides of certain diazabicyclononyl pyrimidine derivatives and their use in the manufacture of pharmaceutical compositions. The compounds of the invention are found to be cholinergic ligands at the nicotinic acetylcholine

NOVEL INDOLYL-OXADIAZOLYL-DIAZABICYCLONONANE DERIVATIVES AND THEIR MEDICAL AND DIAGNOSTICAL USE

This invention relates to novel indolyl-oxadiazolyl-diazabicyclononane derivatives and their use in the manufacture of pharmaceutical compositions. The compounds of the invention are found to be cholinergic ligands at the nicotinic acetylcholine receptors and modulators of the monoamine receptors and transporters. Due to their pharmacological profile the compounds of the invention may be useful for the treatment of diseases or disorders as diverse as those related to the cholinergic system of the central nervous system (CNS), the peripheral nervous system (PNS), diseases or disorders related to smooth muscle contraction, endocrine diseases or disorders, diseases or disorders related to neuro-degeneration, diseases or disorders related to inflammation, pain, and withdrawal symptoms caused by the termination of abuse of chemical substances.