Heterocyclic Building Blocks-Quinuclidine

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

Fujisawa, Yuta published the artcileMechanically Robust, Self-Healable Polymers Usable under High Humidity: Humidity-Tolerant Noncovalent Cross-Linking Strategy, COA of Formula: C13H26N2, the publication is Journal of the American Chemical Society (2021), 143(37), 15279-15285, database is CAplus and MEDLINE.

Although mech. robust polymer materials had not been thought to self-heal, we recently found that poly(ether thiourea) PTUEG₃, which is a glassy polymer with high mech. strength, self-heals even at ambient temperatures This finding updated the above preconception. Nevertheless, it should also be noted that PTUEG₃, under high humidity, absorbs water and is plasticized to lose its mech. strength. Humidity-induced plasticization is a general problem for polymers with polar groups. Herein, we report that PTUEG₃, if designed by copolymerization to contain only 10 mol % of a dicyclohexylmethane (Cy₂M) thiourea unit (TUCy₂M), serves as a humidity-tolerant, mech. robust polymer material that can self-heal at ambient temperatures This copolymer contained, in its ether thiourea (TUEG₃)-rich domain, a humidity-tolerant, noncovalently cross-linked 3D network with mech. robustness formed by stacking of the Cy₂M group. The present work provides a promising design strategy for mech. robust, self-healable polymers usable under high humidity.

Journal of the American Chemical Society 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, COA of Formula: C13H26N2.

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

Flood, Dillon T. published the artcileExpanding Reactivity in DNA-Encoded Library Synthesis via Reversible Binding of DNA to an Inert Quaternary Ammonium Support, Recommanded Product: 4-Cyclohexylbenzoic acid, the publication is Journal of the American Chemical Society (2019), 141(25), 9998-10006, database is CAplus and MEDLINE.

DNA Encoded Libraries have proven immensely powerful tools for lead identification. The ability to screen billions of compounds at once has spurred increasing interest in DEL development and utilization. Although DEL provides access to libraries of unprecedented size and diversity, the idiosyncratic and hydrophilic nature of the DNA tag severely limits the scope of applicable chemistries. It is known that biomacromols. can be reversibly, noncovalently adsorbed and eluted from solid supports, and this phenomenon has been utilized to perform synthetic modification of biomols. in a strategy we have described as reversible adsorption to solid support (RASS). Herein, we present the adaptation of RASS for a DEL setting, which allows reactions to be performed in organic solvents at near anhydrous conditions opening previously inaccessible chem. reactivities to DEL. The RASS approach enabled the rapid development of C(sp²)-C(sp³) decarboxylative cross-couplings with broad substrate scope, an electrochem. amination (the first electrochem. synthetic transformation performed in a DEL context), and improved reductive amination conditions. The utility of these reactions was demonstrated through a DEL-rehearsal in which all newly developed chemistries were orchestrated to afford a compound rich in diverse skeletal linkages. We believe that RASS will offer expedient access to new DEL reactivities, expanded chem. space, and ultimately more drug-like libraries.

Journal of the American Chemical Society 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, Recommanded Product: 4-Cyclohexylbenzoic acid.

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

Kumar, I. V. Sunil published the artcileIdentification, synthesis and characterization of impurities of Montelukast sodium, Related Products of quinuclidine, the publication is Asian Journal of Chemistry (2011), 23(10), 4536-4546, database is CAplus.

Montelukast sodium is a selective leukotriene receptor antagonist [i.e., 1-[[[(1R)-1-[3-[(1E)-2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]cyclopropaneacetic acid sodium salt] which inhibits cysteinyl leukotriene CysLT₁ receptor. Various synthesis methods of Montelukast have been published. During laboratory optimization and later in-bulk synthesis, the formation of various impurities was detected. Besides, a Pharma Europa draft mentions nine process-related impurities. However, the method of preparation of most of these impurities is not available in the literature. Also, different route of synthesis will have different impurity profile and those process related impurities are not covered in pharmacopeia issues. In this study the authors report the synthesis of possible process impurities and the target compounds thus formed include several impurities previously mentioned in Pharma Europa.

Asian 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, Related Products of quinuclidine.

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

Sliozberg, Yelena published the artcileInterface binding and mechanical properties of MXene-epoxy nanocomposites, Safety of 4,4-Diaminodicyclohexyl methane, the publication is Composites Science and Technology (2020), 108124, database is CAplus.

Thermosetting epoxy polymers exhibit excellent stiffness and strength and are commonly utilized as matrixes to make fiber reinforced composites. However, epoxy thermosets are brittle and typically possess a low fracture toughness that restricts their applications. One promising mechanism for improving mech. properties of epoxy is the integration of micro- and nano-scale fillers. MXenes, a large family of 2D transition-metal carbides, carbonitrides, and nitrides, can be used to produce multifunctional polymer nanocomposites due to their excellent elec., thermal, and mech. properties. We employed d. functional theory and coarse-grained mol. dynamics simulations to evaluate binding energy and microscopic mechanisms of fracture under uniaxial tension for MXene-epoxy composites. The simulation results were verified by manufacturing Ti₃C₂Tx MXene-epoxy composites and studying their structure and fracture surfaces. Binding between Ti₃C₂Tx and epoxy becomes stronger with less hydrogen coverage of Ti₃C₂Tx surface due to increase in favorable electrostatic interactions. At higher filler contents, the increase of the modulus is reduced due to filler aggregation. Void formation was detected near edges of the particles in MXene-epoxy composites under deformation from both exptl. and simulation studies of the fracture surfaces. From these observations, we expect the MXene fillers to improve epoxy toughness and enhance its mech. performance.

Composites Science and Technology 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 C11H8N2O2, Safety of 4,4-Diaminodicyclohexyl methane.

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