Heterocyclic Building Blocks-Quinuclidine

Habicht, J. published the artcileInhibition of prostaglandin E₂ release by salicylates, benzoates and phenols: a quantitative structure-activity study, SDS of cas: 20029-52-1, the publication is Journal of Pharmacy and Pharmacology (1983), 35(11), 718-23, database is CAplus and MEDLINE.

Concentrations inhibiting 50% of PGE₂  [363-24-6] release from phorbol ester-stimulated mouse peritoneal macrophages in vitro were determined for monosubstituted congeners of salicylic acid, benzoic acid, and phenol. Other compounds, mainly benzoic acids, were inactive. An attempt was made to establish QSAR from the exptl. data using literature or calculated values for the logarithmic octanol-water partition coefficients of the compounds, molar refractivity and sigma values of substituents as well as structural indicator variables. The equations had moderate predictive power and should be considered as a 1st step in the investigation of factors determining the biog. activity of salicylates, benzoates, and phenols.

Journal of Pharmacy and Pharmacology 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, SDS of cas: 20029-52-1.

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

Eaton, Matthew D. published the artcileTemperature dependent fracture behavior in model epoxy networks with nanoscale heterogeneity, Application In Synthesis of 1761-71-3, the publication is Polymer (2021), 123560, database is CAplus.

The role of nanoscale heterogeneity on the mode I fracture toughness, K_Ic, of model epoxy networks has been investigated. Model systems utilized consist of diglycidyl ether of bisphenol A (DGEBA) as the epoxide with a stoichiometric amine mixture of a rigid cycloaliphatic diamine (PACM) and a more flexible, polypropylene glycol based diamine (Jeffamine) at different molar ratios. The mol. weight of the Jeffamine was adjusted to further tailor the epoxy properties. Fracture toughness was measured using single edge notched bend samples and hardness was measured by Vickers indentation. Both measurements were performed at temperatures as low as -100°C to above ambient temperatures Results are interpreted in the context of the Dugdale model of material toughness where the fracture toughness is expressed in terms of a cohesive zone stress (related to the hardness), the elastic modulus (measured directly) and the crack tip opening displacement (obtained from images of the fracture surfaces). High toughness is obtained in heterogeneous networks where a decrease in the cohesive zone stress is offset by sufficiently large increases in the crack tip opening displacement.

Polymer 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, Application In Synthesis of 1761-71-3.

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

Cordonnier, Axel published the artcileSynthesis and in vitro preliminary evaluation of prostate-specific membrane antigen targeted upconversion nanoparticles as a first step towards radio/fluorescence-guided surgery of prostate cancer, Synthetic Route of 1353016-70-2, the publication is Journal of Materials Chemistry B: Materials for Biology and Medicine (2021), 9(36), 7423-7434, database is CAplus and MEDLINE.

Over the last decade, upconversion nanoparticles (UCNP) have been widely investigated in nanomedicine due to their high potential as imaging agents in the near-IR (NIR) optical window of biol. tissues. Here, we successfully develop active targeted UCNP as potential probes for dual NIR-NIR fluorescence and radioactive-guided surgery of prostate-specific membrane antigen (PSMA)(+) prostate cancers. We designed a one-pot thermolysis synthesis method to obtain oleic acid-coated spherical NaYF₄:Yb,Tm@NaYF₄ core/shell UCNP with narrow particle size distribution (30.0 ± 0.1 nm, as estimated by SAXS anal.) and efficient upconversion luminescence. Polyethylene glycol (PEG) ligands bearing different anchoring groups (phosphate, bis- and tetra-phosphonate-based) were synthesized and used to hydrophilize the UCNP. DLS studies led to the selection of a tetra-phosphonate PEG(2000) ligand affording water-dispersible UCNP with sustained colloidal stability in several aqueous media. PSMA-targeting ligands (i.e., glutamate-urea-lysine derivatives called KuEs) and fluorescent or radiolabeled prosthetic groups were grafted onto the UCNP surface by strain-promoted azide-alkyne cycloaddition (SPAAC). These UCNP, coated with 10 or 100% surface d. of KuE ligands, did not induce cytotoxicity over 24 h incubation in LNCaP-Luc or PC3-Luc prostate cancer cell lines or in human fibroblasts for any of the concentrations evaluated. Competitive binding assays and flow cytometry demonstrated the excellent affinity of UCNP@KuE for PSMA-pos. LNCaP-Luc cells compared with non-targeted UCNP@CO₂H. Furthermore, the binding of UCNP@KuE to prostate tumor cells was pos. correlated with the surface d. of PSMA-targeting ligands and maintained after ¹²⁵I-radiolabelling. Finally, a preliminary biodistribution study in LNCaP-Luc-bearing mice demonstrated the radiochem. stability of non-targeted [^125I]UCNP paving the way for future in vivo assessments.

Journal of Materials Chemistry B: Materials for Biology and Medicine 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, Synthetic Route of 1353016-70-2.

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

Bizet, Vincent published the artcileDirect Access to Furoindolines by Palladium-Catalyzed Intermolecular Carboamination, Recommanded Product: 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, the publication is ACS Catalysis (2016), 6(10), 7183-7187, database is CAplus.

A versatile Pd-catalyzed intermol. syn-carboamination of dihydrofurans giving access to the ubiquitous furoindoline motif is described. The efficiency of the process relies on the use of Buchwald-type biarylphosphines and the perfect control for site-selectivity of Pd insertion across the C=C bond. A catalytic sequence consisting of Heck and carboamination cross-coupling reactions from readily available dihydrofurans affords-in usually high chem. yields and high levels of diastereocontrol-poly(hetero)cyclic compounds that would be difficult to access by established methods. Encouraging preliminary results for the enantioselective carboamination of 2,3-dihydrofurans are also disclosed.

ACS Catalysis published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C28H41N2P, Recommanded Product: 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine.

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

Singh, Ritesh published the artcileP450-Catalyzed Intramolecular sp³ C-H Amination with Arylsulfonyl Azide Substrates, COA of Formula: C13H16O2, the publication is ACS Catalysis (2014), 4(2), 546-552, database is CAplus and MEDLINE.

The direct amination of aliphatic C-H bonds represents a most valuable transformation in organic chem. While a number of transition-metal-based catalysts have been developed and investigated for this purpose, the possibility to execute this transformation with biol. catalysts has remained largely unexplored. Here, we report that cytochrome P 450 enzymes can serve as efficient catalysts for mediating intramol. benzylic C-H amination reactions in a variety of arylsulfonyl azide compounds Under optimized conditions, the P 450 catalysts were found to support up to 390 total turnovers leading to the formation of the desired sultam products with excellent regioselectivity. In addition, the chiral environment provided by the enzyme active site allowed for the reaction to proceed in a stereo- and enantioselective manner. The C-H amination activity, substrate profile, and enantio/stereoselectivity of these catalysts could be modulated by utilizing enzyme variants with engineered active sites.

ACS Catalysis 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 C17H14O5, COA of Formula: C13H16O2.

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

Zhao, Guohua published the artcileSynthesis of potent and selective 2-azepanone inhibitors of human tryptase, Quality Control of 20029-52-1, the publication is Bioorganic & Medicinal Chemistry Letters (2004), 14(2), 309-312, database is CAplus and MEDLINE.

The serine protease tryptase has been associated with a broad range of allergic and inflammatory diseases and, in particular, has been implicated as a critical mediator of asthma. The inhibition of tryptase therefore has the potential to be a valuable therapy for asthma. The synthesis, employing solution phase parallel methods, and SAR of a series of novel 2-azepanone tryptase inhibitors are presented. One member of this series, I, was identified as a potent inhibitor of human tryptase (IC₅₀ 38 nM) with selectivity ≤330-fold vs. related serine proteases (trypsin, plasmin, uPA, tPA, APC, alpha-thrombin, and FXa).

Bioorganic & Medicinal Chemistry Letters 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 C8H7ClO3, Quality Control of 20029-52-1.

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

Sutton, James C. published the artcileSolid-phase synthesis and SAR of 4-carboxy-2-azetidinone mechanism-based tryptase inhibitors, Application of 4-Cyclohexylbenzoic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2004), 14(9), 2233-2239, database is CAplus and MEDLINE.

A series of non-guanidine N1-activated C4-carboxy azetidinone tryptase inhibitors, e.g. I, was prepared by solid-phase methodol. to quickly assess the SAR associated with distal functionality on the N1-activating group. From these studies, potent inhibitors with improved specificity were discovered.

Bioorganic & Medicinal Chemistry Letters 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 C5H9IO2, Application of 4-Cyclohexylbenzoic acid.

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

Ruiz-Castillo, Paula published the artcileRational Ligand Design for the Arylation of Hindered Primary Amines Guided by Reaction Progress Kinetic Analysis, Application of 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, the publication is Journal of the American Chemical Society (2015), 137(8), 3085-3092, database is CAplus and MEDLINE.

The authors report the Pd-catalyzed arylation of very hindered α,α,α-trisubstituted primary amines. Kinetics-based mechanistic anal. and rational design led to the development of two biarylphosphine ligands that allow the transformation to proceed with excellent efficiency. The process was effective in coupling a wide range of functionalized aryl and heteroaryl halides under mild conditions.

Journal of the American Chemical Society published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C28H41N2P, Application of 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine.

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

Borrajo-Calleja, Gustavo M. published the artcileMechanistic Investigation of the Pd-Catalyzed Intermolecular Carboetherification and Carboamination of 2,3-Dihydrofuran: Similarities, Differences, and Evidence for Unusual Reaction Intermediates, Related Products of quinuclidine, the publication is Organometallics (2017), 36(18), 3553-3563, database is CAplus.

The mechanism of the Pd-catalyzed intermol. syn carboetherification and syn carboamination of 2,3-dihydrofuran was studied exptl. Crystallog., spectroscopic, and spectrometric methods have shed light on the nature of a number of catalytically competent Pd complexes. Several oxidative addition complexes as well as their cationic derivatives were characterized by x-ray diffraction analyses. In the latter, the complexes derived from 2-bromophenol displayed an unorthodox η⁶ binding mode of the privileged Buchwald-type dialkylbiarylphosphine ligands. The hemilabile character of this interaction was found to facilitate coordination of the polarized olefinic substrate, as evidenced by NMR spectroscopy. In contrast, coordination of the pendant sulfonyl group in the cationic complexes derived from 2-bromo-N-sulfonylated anilines prevented direct binding of 2,3-dihydrofuran. Deprotonation of these species induced aggregation of monomeric units through various weak noncovalent interactions to generate trinuclear Pd clusters. The reversibility of this process was probed by conducting crossover experiments The nature of the alkali ion strongly influences the selectivity of the assembly phenomenon. Examination of the importance of the nucleophilicity in these intermol. reactions revealed that the switch between syn carbofunctionalization and Heck arylation of 2,3-dihydrofuran certainly arose from a zwitterionic intermediate common to both catalytic manifolds. The understanding of these reactions gained through this study should certainly favor the design of novel Pd-catalyzed transformations for related systems.

Organometallics published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C28H41N2P, Related Products of quinuclidine.

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

Yu, Peng published the artcileIridium-Catalyzed Hydrochlorination and Hydrobromination of Alkynes by Shuttle Catalysis, Related Products of quinuclidine, the publication is Angewandte Chemie, International Edition (2020), 59(7), 2904-2910, database is CAplus and MEDLINE.

Described herein are two different methods for the synthesis of vinyl halides by a shuttle catalysis based iridium-catalyzed transfer hydrohalogenation of unactivated alkynes. The use of 4-chlorobutan-2-one or tert-Bu halide as donors of hydrogen halides allows this transformation in the absence of corrosive reagents, such as hydrogen halides or acid chlorides, thus largely improving the functional-group tolerance and safety profile of these reactions compared to the state-of-the-art. This method has granted access to alkenyl halide compounds containing acid-sensitive groups, such as tertiary alcs., silyl ethers, and acetals. The synthetic value of those methodologies has been demonstrated by gram-scale synthesis where low catalyst loading was achieved.

Angewandte Chemie, International Edition published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C18H10, Related Products of quinuclidine.

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