Category: quinuclidine

Hatter, Christine B. published the artcileMicromechanical response of two-dimensional transition metal carbonitride (MXene) reinforced epoxy composites, Name: 4,4-Diaminodicyclohexyl methane, the publication is Composites, Part B: Engineering (2020), 107603, database is CAplus.

MXenes have attracted much attention as fillers in polymer composites due to their superior elec. and mech. properties making them ideal for creating multifunctional composites. In this work, Ti₃CN-epoxy composites were prepared via solvent processing and cured with amine-based hardener. The effects of Ti₃CN content in the epoxy system on the thermal degradation behavior and micromech. properties were investigated. The extent of intercalation of epoxy between MXene flakes was analyzed by transmission electron microscopy. Nanoindentation anal. of MXene-epoxy composites exhibited improved mech. properties with increasing MXene content with highest increase to 12.8 GPa Young’s modulus for 90 wt% Ti₃CN. An increase in creep resistance of composites was observed at maximum loading of Ti₃CN by 46% compared to neat epoxy.

Composites, Part B: Engineering published new progress about 1761-71-3. 1761-71-3 belongs to quinuclidine, auxiliary class Ploymers, name is 4,4-Diaminodicyclohexyl methane, and the molecular formula is C13H26N2, Name: 4,4-Diaminodicyclohexyl methane.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

White, James D. published the artcileIron catalyzed enantioselective sulfa-Michael addition: a four-step synthesis of the anti-asthma agent Montelukast, SDS of cas: 162515-68-6, the publication is Chemical Science (2014), 5(6), 2200-2204, database is CAplus.

A salen ligand based on a chiral cis-2,5-diaminobicyclo[2.2.2]octane scaffold forms an iron(iii) complex with ferric chloride which catalyzed asym. addition of thiols to α,β-unsaturated ketones under mild conditions. The reaction (sulfa-Michael addition) produces β-thioketones in excellent yield and high enantiomeric excess from a wide range of aliphatic and aromatic thiols using chalcones and other conjugated enones as Michael acceptors. With α-substituted α,β-unsaturated ketones as acceptors, the addition showed strong preference (typically >50 : 1) for the syn diastereomer over the anti product. An asym. synthesis of (R)-Montelukast, the sodium salt of which is the com. anti-asthma drug Singulair, was devised using conjugate addition of a thiol catalyzed by our iron(III)-salen complex to an α,β-unsaturated ketone synthesized in a four-component, one-pot tandem Michael-aldol condensation. The reaction sequence to (R)-Montelukast proceeded in 72% overall yield over four steps from com. available materials. A mechanism for our catalyzed asym. sulfa-Michael addition was advance which coordinates the enone acceptor to the metal center of the iron-salen complex in an open lower quadrant under the bicyclic scaffold, thereby exposing only the si face of the double bond to attack by the external nucleophilic thiol. Prior internal coordination of the thiol to the metal center of the complex is proposed based on spectroscopic and chem. evidence and leads to activation of the catalyst through a trans ligand effect.

Chemical Science published new progress about 162515-68-6. 162515-68-6 belongs to quinuclidine, auxiliary class Thiol,Carboxylic acid,Aliphatic cyclic hydrocarbon, name is 2-(1-(Mercaptomethyl)cyclopropyl)acetic acid, and the molecular formula is C9H20Cl2Si, SDS of cas: 162515-68-6.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Tang, Yitian published the artcileEfficient Synthesis of γ-Lactones by Cobalt-Catalyzed Carbonylative Ring Expansion of Oxetanes under Syngas Atmosphere, Formula: C6H10O2S, the publication is ChemCatChem (2020), 12(23), 5898-5902, database is CAplus.

A practical route from oxetanes or thietanes to γ-(thio)butyrolactones via solvated-proton-assisted cobalt-catalyzed carbonylative ring expansion under syngas atm. were reported. A wide variety of γ-(thio)butyrolactones were afforded in a good to excellent yields. The versatility of this method were well demonstrated in the synthesis of intermediates towards the natural product Arctigenin as well as the pharmaceuticals Baclofen and Montelukast. The observed promoting effect of glycol ether solvent were rationally interpreted.

ChemCatChem published new progress about 162515-68-6. 162515-68-6 belongs to quinuclidine, auxiliary class Thiol,Carboxylic acid,Aliphatic cyclic hydrocarbon, name is 2-(1-(Mercaptomethyl)cyclopropyl)acetic acid, and the molecular formula is C6H12N2O, Formula: C6H10O2S.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Qiu, Wenting published the artcileA Mild, General, Metal-Free Method for Desulfurization of Thiols and Disulfides Induced by Visible-Light, Product Details of C6H10O2S, the publication is Chinese Journal of Chemistry (2021), 39(5), 1255-1258, database is CAplus.

A visible-light-induced metal-free desulfurization method for thiols and disulfides was explored. This radical desulfurization featured mild conditions, robustness, and excellent functionality compatibility. It was successfully applied not only to the desulfurization of small mols., but also to peptides.

Chinese Journal of Chemistry published new progress about 162515-68-6. 162515-68-6 belongs to quinuclidine, auxiliary class Thiol,Carboxylic acid,Aliphatic cyclic hydrocarbon, name is 2-(1-(Mercaptomethyl)cyclopropyl)acetic acid, and the molecular formula is C6H10O2S, Product Details of C6H10O2S.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Gawel, Justyna M. published the artcilePTG-0861: A novel HDAC6-selective inhibitor as a therapeutic strategy in acute myeloid leukaemia, Category: quinuclidine, the publication is European Journal of Medicinal Chemistry (2020), 112411, database is CAplus and MEDLINE.

Dysregulated Histone Deacetylase (HDAC) activity across multiple human pathologies have highlighted this family of epigenetic enzymes as critical druggable targets, amenable to small mol. intervention. While efficacious, current approaches using non-selective HDAC inhibitors (HDACi) have been shown to cause a range of undesirable clin. toxicities. To circumvent this, recent efforts have focused on the design of highly selective HDACi as a novel therapeutic strategy. Beyond roles in regulating transcription, the unique HDAC6 (with two catalytic domains) regulates the deacetylation of α-tubulin; promoting growth factor-controlled cell motility, cell division, and metastatic hallmarks. Recent studies have linked aberrant HDAC6 function in various hematol. cancers including acute myeloid leukemia and multiple myeloma. Herein, we report the discovery, in vitro characterization, and biol. evaluation of PTG-0861 (JG-265), a novel HDAC6-selective inhibitor with strong isoenzyme-selectivity (∼36x ) and low nanomolar potency (IC₅₀ = 5.92 nM) against HDAC6. This selectivity profile was rationalized via in silico docking studies and also observed in cellulo through cellular target engagement. Moreover, PTG-0861 achieved relevant potency against several blood cancer cell lines (e.g. MV4-11, MM1S), while showing limited cytotoxicity against non-malignant cells (e.g. NHF, HUVEC) and CD-1 mice. In examining compound stability and cellular permeability, PTG-0861 revealed a promising in vitro pharmacokinetic (PK) profile. Altogether, in this study we identified a novel and potent HDAC6-selective inhibitor (∼4x more selective than current clin. standards – citarinostat, ricolinostat), which achieves cellular target engagement, efficacy in hematol. cancer cells with a promising safety profile and in vitro PK.

European Journal of Medicinal Chemistry published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C13H16O2, Category: quinuclidine.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Koshel, S. G. published the artcileSynthesis of cyclohexylbenzoic acids by liquid-phase catalytic oxidation of cyclohexyltoluenes, Synthetic Route of 20029-52-1, the publication is Neftekhimiya (1989), 29(2), 257-61, database is CAplus.

Isomeric cyclohexyltoluenes were oxidized by mol. oxygen in glacial AcOH using Co(OAc)₂ as catalyst and AcH as initiator. The reactivity of the cyclohexyltoluene decreased in the order: p– > m– > o-isomer.

Neftekhimiya published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C13H16O2, Synthetic Route of 20029-52-1.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Butler, Christopher R. published the artcileAminomethyl-Derived Beta Secretase (BACE1) Inhibitors: Engaging Gly230 without an Anilide Functionality, Safety of 3-(Trifluoromethyl)oxetan-3-amine hydrochloride, the publication is Journal of Medicinal Chemistry (2017), 60(1), 386-402, database is CAplus and MEDLINE.

A growing subset of β-secretase (BACE1) inhibitors for the treatment of Alzheimer’s disease (AD) utilizes an anilide chemotype that engages a key residue (Gly230) in the BACE1 binding site. Although the anilide moiety affords excellent potency, it simultaneously introduces a third hydrogen bond donor that limits brain availability and reveals a potential metabolic site leading to the formation of an aniline, a structural motif of potential safety concern. The authors report herein an alternative aminomethyl linker that delivers similar potency and improved brain penetration relative to the amide moiety. Optimization of this series identified analogs with an excellent balance of ADME properties and potency, however potential drug-drug interactions (DDI) were predicted based on CYP2D6 affinities. Generation and anal. of key BACE1 and CYP2D6 crystal structures identified strategies to obviate the DDI liability, leading to compound I which exhibits robust in vivo efficacy as a BACE1 inhibitor.

Journal of Medicinal Chemistry published new progress about 1268883-21-1. 1268883-21-1 belongs to quinuclidine, auxiliary class Trifluoromethyl,Fluoride,Oxetane,Salt,Amine, name is 3-(Trifluoromethyl)oxetan-3-amine hydrochloride, and the molecular formula is C4H7ClF3NO, Safety of 3-(Trifluoromethyl)oxetan-3-amine hydrochloride.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Fujiwara, Eisuke published the artcileUltrafast Spectroscopic Analysis of Pressure-Induced Variations of Excited-State Energy and Intramolecular Proton Transfer in Semi-Aliphatic Polyimide Films, Safety of 4,4-Diaminodicyclohexyl methane, the publication is Journal of Physical Chemistry B (2021), 125(9), 2425-2434, database is CAplus and MEDLINE.

The relationship between the photoexcitation dynamics and the structures of semi-aliphatic polyimides (3H-PIs) was investigated using ultrafast fluorescent emission spectroscopy at atm. and increased pressures of up to 4 GPa. The 3H-PI films exhibited prominent fluorescence with extremely large Stokes shifts (Δν > 10 000 cm^-1) through an excited-state intramol. proton transfer (ESIPT) induced by keto-enol tautomerism at the isolated dianhydride moiety. The incorporation of bulky -CH₃ and -CF₃ side groups at the diamine moiety of the PIs increased the quantum yields of the ESIPT fluorescence owing to an enhanced interchain free volume In addition, 3H-PI films emitted another fluorescence at shorter wavelengths originating from closely packed polyimide (PI) chains (in aggregated forms), which was mediated through a Foddorster resonance energy transfer (FRET) from an isolated enol form into aggregated forms. The FRET process became more dominant than the ESIPT process at higher pressures owing to an enhancement of the FRET efficiency caused by the increased dipole-dipole interactions associated with a densification of the PI chain packing. The efficiency of the FRET rapidly increased by applying pressure up to 1 GPa owing to an effective compression of the interchain free volume and addnl. gradually increased at higher pressures owing to structural and/or conformational changes in the main chains.

Journal of Physical Chemistry B published new progress about 1761-71-3. 1761-71-3 belongs to quinuclidine, auxiliary class Ploymers, name is 4,4-Diaminodicyclohexyl methane, and the molecular formula is C13H26N2, Safety of 4,4-Diaminodicyclohexyl methane.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Nara, Mayuko published the artcileWhite-Light Emission and Tunable Luminescence Colors of Polyimide Copolymers Based on FRET and Room-Temperature Phosphorescence, Quality Control of 1761-71-3, the publication is ACS Omega (2020), 5(24), 14831-14841, database is CAplus and MEDLINE.

Thermally stable copolyimide (CoPI) films exhibiting high optical transparency and room-temperature phosphorescence (RTP) were prepared by copolymerizing fluorescent dianhydride and brominated phosphorescent dianhydride with an alicyclic diamine. The CoPI films underwent a 5 wt % degradation at a temperature higher than 349°C and exhibited dual fluorescent and phosphorescent emissions owing to their efficient Forster resonance energy transfer from the fluorescent to phosphorescent dianhydride moieties in the main chains, followed by an intersystem crossing from the singlet to triplet state of the latter moiety atoms. The CoPIs displayed bright RTP under a vacuum with various colors produced when adjusting the copolymerization ratio. CoPI with 5 mol % phosphorescent moiety (CoPI-05) emitted white light with high optical transparency owing to the suppression of the PI chain aggregation that causes a yellowish coloration. The copolymerization of fluorescent and phosphorescent PI moieties can control the photoluminescent properties of PI films and is applicable to color-tunable solid-state emitters, ratiometric oxygen sensors, and solar-spectrum converters.

ACS Omega published new progress about 1761-71-3. 1761-71-3 belongs to quinuclidine, auxiliary class Ploymers, name is 4,4-Diaminodicyclohexyl methane, and the molecular formula is C13H26N2, Quality Control of 1761-71-3.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

LeValley, Paige J. published the artcileDesign of functionalized cyclic peptides through orthogonal click reactions for cell culture and targeting applications, Formula: C19H15NO3, the publication is Chemical Communications (Cambridge, United Kingdom) (2018), 54(50), 6923-6926, database is CAplus and MEDLINE.

An approach for the design of functionalized cyclic peptides is established for use in 3D cell culture and in cell targeting. Sequential orthogonal click reactions, specifically a photoinitiated thiol-ene and strain promoted azide-alkyne cycloaddition, were utilized for peptide cyclization and conjugation relevant for biomaterial and biomedical applications, resp.

Chemical Communications (Cambridge, United Kingdom) published new progress about 1353016-70-2. 1353016-70-2 belongs to quinuclidine, auxiliary class Other Aromatic Heterocyclic,Carboxylic acid,Amide,Inhibitor,Inhibitor, name is Dbco-acid, and the molecular formula is C19H15NO3, Formula: C19H15NO3.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider