Month: November 2022

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

Ponzano, Stefano published the artcileSynthesis, Biological Evaluation, and 3D QSAR Study of 2-Methyl-4-oxo-3-oxetanylcarbamic Acid Esters as N-Acylethanolamine Acid Amidase (NAAA) Inhibitors, Application of 4-Cyclohexylbenzoic acid, the publication is Journal of Medicinal Chemistry (2014), 57(23), 10101-10111, database is CAplus and MEDLINE.

N-(2-Oxo-3-oxetanyl)carbamic acid esters e. g., I, have recently been reported to be noncompetitive inhibitors of the N-acylethanolamine acid amidase (NAAA) potentially useful for the treatment of pain and inflammation. In the present study, we further explored the structure-activity relationships of the carbamic acid ester side chain of 2-methyl-4-oxo-3-oxetanylcarbamic acid ester derivatives Addnl. favorable features in the design of potent NAAA inhibitors have been found together with the identification of a single digit nanomolar inhibitor. In addition, we devised a 3D QSAR using the at. property field method. The model turned out to be able to account for the structural variability and was prospectively validated by designing, synthesizing, and testing novel inhibitors. The fairly good agreement between predictions and exptl. potency values points to this 3D QSAR model as the first example of quant. structure-activity relationships in the field of NAAA inhibitors .

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, Application of 4-Cyclohexylbenzoic acid.

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

Gholivand, Khodayar published the artcileSynthesis, characterized, QSAR studies and molecular docking of some phosphonates as COVID-19 inhibitors, Name: 4,4-Diaminodicyclohexyl methane, the publication is Polyhedron (2022), 115824, database is CAplus and MEDLINE.

The global coronavirus (COVID-19) outbreak has prompted scientists to discover a cure for the disease. So far, phosphorus-based drugs have been proposed. These drugs have good inhibitory activity against the main protease (Mpro). Hence, in order to introduce a group of inhibitors the coronavirus, 51 compounds containing different mono, bis, and tetra phosphonates as Remdesivir derivatives, 32 of which are new, were synthesized and characterized by ³¹P, ¹³C, and ¹H NMR and IR spectroscopy. Their biol. activities were also investigated by Mol. Docking, QSAR, and Pharmacophore. Van der Waals, hydrogen bonding, and hydrophobic interactions were studied for all compounds as well as binding energy (ΔG, Kcal/mol) and the inhibitory constant Ki (μM) obtained by Mol. Docking. The results showed that the topol. of the ligands and the change of the different groups attached to them can be effective in the placement position in the active site of the enzyme (Glu 166 and Gln 189). And bisphosphonates have a high interaction tendency with Mpro COVID-19. Compound L24 was identified as the best inhibitor with the -6.38 kcal/mol binding energy. The quant. structure-activity relationship (QSAR) findings demonstrated that the polarity and topol. of mols. in all phosphonate derivatives were important parameters affecting the effecting on the binding energy and inhibitory ability of compounds The DFT and pharmacophore results are in good accordance with those of QSAR and mol. docking. This study can be helpful to gain a better understanding of the interactions between the Mpro of virus and its inhibitors in order to attain drugs with more effect on coronavirus (COVID-19).

Polyhedron 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

Strom, Alexandra E. published the artcileSynthetic and Computational Studies on the Rhodium-Catalyzed Hydroamination of Aminoalkenes, HPLC of Formula: 1160556-64-8, the publication is ACS Catalysis (2016), 6(9), 5651-5665, database is CAplus and MEDLINE.

The influence of ligand structure on rhodium-catalyzed hydroamination has been evaluated for a series of phosphinoarene ligands. These catalysts have been evaluated in a set of catalytic intramol. Markovnikov hydroamination reactions. The mechanism of hydroamination catalyzed by the rhodium(I) complexes in this study was examined computationally, and the turnover-limiting step was elucidated. These computational studies were extended to a series of theor. hydroamination catalysts to compare the electronic effects of the ancillary ligand substituents. The relative energies of intermediates and transition states were compared to those of intermediates in the reaction catalyzed by the unsubstituted catalyst. The exptl. difference in the reactivities of electron-rich and electron-poor catalysts was compared to the computational results, and it was found that the activity for the electron-poor catalysts predicted from the reaction barriers was overestimated. Thus, the anal. of the catalysts in this study was expanded to include the binding preference of each ligand, in comparison to that of the unsubstituted ligand. This information accounts for the disparity between observed reactivity and the calculated overall reaction barrier for electron-poor ligands. The ligand-binding preferences for new ligand structures were calculated, and ligands that were predicted to bind strongly to rhodium generated catalysts for the exptl. catalytic reactions that were more reactive than those predicted to bind more weakly.

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 C6H12N2O, HPLC of Formula: 1160556-64-8.

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

Bernard-Gauthier, Vadim published the artcileDevelopment of subnanomolar radiofluorinated (2-pyrrolidin-1-yl)imidazo[1,2-b]pyridazine pan-Trk inhibitors as candidate PET imaging probes, Recommanded Product: 3-Fluorocyclobutanamine hydrochloride, the publication is MedChemComm (2015), 6(12), 2184-2193, database is CAplus.

Dysregulation of tropomyosin receptor kinases (TrkA/B/C) expression and signalling is recognized as a hallmark of numerous neurodegenerative diseases including Parkinson’s, Huntington’s and Alzheimer’s disease. TrkA/B/C is known to drive tumorogensis and metastatic potential in a wide range of neurogenic and non-neurogenic human cancers. The development of suitable positron emission tomog. (PET) radioligands would allow an in vivo exploration of this versatile potential therapeutic target. Herein, the rational remodeling of the amide moiety of a 6-(2-(3-fluorophenyl)pyrrolidin-1-yl)imidazo[1,2-b]pyridazine-3-amide lead structure to accommodate efficient fluorine-18 labeling led to the identification of a series of fluorinated Trk inhibitors with picomolar IC₅₀. The ensuing representative radiolabeled inhibitors [¹⁸F]16 ([¹⁸F]-(±)-IPMICF6) and [¹⁸F]27 ([¹⁸F]-(±)-IPMICF10) constitute novel lead radioligands with about 2- to 3- orders of magnitude increased TrkB/C potencies compared to previous lead tracers and display favorable selectivity profiles and physicochem. parameters for translation into in vivo PET imaging agents.

MedChemComm published new progress about 1284245-36-8. 1284245-36-8 belongs to quinuclidine, auxiliary class Fluoride,Salt,Amine,Aliphatic cyclic hydrocarbon, name is 3-Fluorocyclobutanamine hydrochloride, and the molecular formula is C4H9ClFN, Recommanded Product: 3-Fluorocyclobutanamine hydrochloride.

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

Shevchenko, V. P. published the artcileEfficiency of the isotope exchange between sodium 4-phenylbenzoate and tritium under different activation conditions, Application of 4-Cyclohexylbenzoic acid, the publication is Doklady Physical Chemistry (2015), 463(2), 182-187, database is CAplus.

It has been shown that when a mixture of sodium 4-phenylbenzoate and 5% Pd/C preliminarily exposed to a mol. tritium atm. at 333 K for 25 min is treated with at. protium, tritium is incorporated into sodium 4-phenylbenzoate mols. The resulting molar radioactivity of this compound is as high as 0.8 ± 0.2 Ci/mmol, and the molar radioactivity of 4-cyclohexylbenzoic acid turns out to be fourto-five times higher than that of labeled sodium 4-phenylbenzoate. It has been suggested that the interaction of protium atoms with (³H+)(e̅) clusters formed on the support surface upon tritium spillover can initiate isotope exchange and hydrogenation reactions.

Doklady Physical 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 C12H20O6, Application of 4-Cyclohexylbenzoic acid.

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

Zareanshahraki, F. published the artcileSynthesis of non-isocyanate polyurethanes and their application in radiation-curable aerospace coatings, SDS of cas: 1761-71-3, the publication is Progress in Organic Coatings (2020), 105394, database is CAplus.

In this study, a series of sustainable UV-curable non-isocyanate urethane acrylate (NIPU-AC) oligomers, with different structures and acrylate equivalent weights, were synthesized and used as a primary building block of UV-curable coatings for aerospace applications. Synthesis of the NIPU-AC oligomers was carried out in three steps: First, multi-functional cyclic carbonates (MFCC) were prepared by carbonation of aliphatic epoxy compounds under mild temperature and pressure conditions in the presence of a catalyst. In the next step, amine-terminated polyurethane oligomers (PUPAs) were synthesized by the reaction of MFCCs with a stoichiometric excess amount of aliphatic and cycloaliphatic amines. (meth)acrylate functionality was then introduced by direct reaction of amine groups at the chain ends of PUPAs with methacrylic anhydride (MAAH). Finally, UV-curable NIPU coatings, as a new generation of sustainable coatings for aerospace applications, were developed and evaluated for aerospace-critical performance properties, such as low-temperature flexibility and resistance to specific chems./fluids. The results showed that flexibility at -54°C (no cracks or delamination at 1/8″), and good chem. resistance (MEK double rubs > 90, and no significant change in the appearance regarding the fluids) could be reached through the proper design of NIPU-ACs, selection of appropriate reactive diluents, and UV-cure conditions.

Progress in Organic Coatings 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 C14H20BClO2, SDS of cas: 1761-71-3.

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