Heterocyclic Building Blocks-Quinuclidine

Yamaoka, Nagahisa published the artcileIdentification of novel plasminogen activator inhibitor-1 inhibitors with improved oral bioavailability: Structure optimization of N-acylanthranilic acid derivatives, Product Details of C13H16O2, the publication is Bioorganic & Medicinal Chemistry Letters (2018), 28(4), 809-813, database is CAplus and MEDLINE.

Novel plasminogen activator inhibitor-1 (PAI-1) inhibitors with highly improved oral bioavailability were discovered by structure-activity relationship studies on N-acyl-5-chloroanthranilic acid derivatives Because lipophilic N-acyl groups seemed to be important for the anthranilic acid derivatives to strongly inhibit PAI-1, synthesis of compounds in which 5-chloroanthranilic acid was bound to a variety of highly lipophilic moieties with appropriate linkers was investigated. As the result it appeared that some of the derivatives possessing aryl- or heteroaryl-substituted Ph groups in the acyl chain had potent in vitro PAI-1 inhibitory activity. Oral absorbability of typical compounds was also evaluated in rats, and three compounds which have diverse chem. structure with each other, e.g., I, were selected for further pharmacol. evaluation.

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 C2H3N3, Product Details of C13H16O2.

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

Pasha, Farhan Ahmad published the artcileDFT-based de novo QSAR of phenoloxidase inhibitors, Recommanded Product: 4-Cyclohexylbenzoic acid, the publication is Chemical Biology & Drug Design (2008), 71(5), 483-493, database is CAplus and MEDLINE.

The phenoloxidase or tyrosinase is a key enzyme in insects, which is responsible for hydroxylation of tyrosine into o-quinones via o-diphenols. A series of benzaldehyde thiosemicarbazone, benzaldehyde and benzoic acid families were taken with their pragmatic pIC₅₀ values against phenoloxidase from pieris rapae (Lepidoptera) larvae. D. functional theory-based quant. structure-activity relation (QSAR) analyses were performed to speculate the key interaction. The most fitted four different QSAR models were identified and discussed. The softness, electrophilicity index, molar refractivity and log P were identified as best descriptors; however, the at. values of softness and philicity obtained from Fukui function are more significant than global values. The study reveals that electrostatic and steric fields jointly contribute to activity. To gain further insight, the three-dimensional quant. structure-activity relation (3D-QSAR) analyses were performed using two mol. field techniques: comparative mol. field anal. (CoMFA) and comparative mol. similarity indexes anal. (CoMSIA). The successful 3D-QSAR models were obtained from CoMFA (q² = 0.94, r² = 0.99, r²_pred = 0.92) and CoMSIA (q² = 0.94, r² = 0.98, r²_pred = 0/95). The CoMFA and CoMSIA results indicate that, a bulky and neg. group around sulfur atom but a small and pos. group around nitrogen atom might have good effects on activity. The ortho and meta positions of ring are favorable for small group. These QSAR models might be helpful to design the novel and potent inhibitors.

Chemical Biology & Drug Design 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

Cuypers, Thomas published the artcileNi-Catalyzed reductive amination of phenols with ammonia or amines into cyclohexylamines, Product Details of C13H26N2, the publication is Green Chemistry (2020), 22(6), 1884-1893, database is CAplus.

Phenol and its derivatives, which naturally occur in lignocellulose, can be considered as a renewable feedstock not only for aromatic, but also for alicyclic compounds, such as primary and N-substituted cyclohexylamines. So far, the latter are mostly produced from non-renewable starting materials like benzene via problematic nitration/reduction or cross-coupling routes. Herein, an efficient reductive amination of phenol with ammonia or amines is demonstrated, for the first time without the need for rare and expensive noble metals and without using any additives. Various supported Ni catalysts were screened and we elucidated the influence of the key parameters, including the acid-base properties of the supporting material. Acquired knowledge was then applied to different phenol-ammonia/amine combinations, resulting in the synthesis of various primary, secondary and tertiary cyclohexylamines in fair to very high yields.

Green Chemistry 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, Product Details of C13H26N2.

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

Santiago, Celine B. published the artcileDeveloping a Modern Approach To Account for Steric Effects in Hammett-Type Correlations, Synthetic Route of 20029-52-1, the publication is Journal of the American Chemical Society (2016), 138(40), 13424-13430, database is CAplus and MEDLINE.

The effects of aryl ring ortho-, meta-, and para-substitution on site selectivity and enantioselectivity were investigated in the following reactions: (1) enantioselective Pd-catalyzed redox-relay Heck reaction of arylboronic acids, (2) Pd-catalyzed β-aryl elimination of triarylmethanols, and (3) benzoylformate decarboxylase-catalyzed enantioselective benzoin condensation of benzaldehydes. Through these studies, it is demonstrated that the electronic and steric effects of various substituents on selectivities obtained in these reactions can be described by NBO charges, the IR carbonyl stretching frequency, and Sterimol values of various substituted benzoic acids. An extended compilation of NBO charges and IR carbonyl stretching frequencies of various substituted benzoic acids was used as an alternative to Hammett values. These parameters provide a correlative tool that allows for the anal. of a much greater range of substituent effects because they can also account for proximal and remote steric effects.

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, Synthetic Route of 20029-52-1.

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

Charrier, Jean-Damien published the artcileDiscovery and Structure-Activity Relationship of 3-Aminopyrid-2-ones as Potent and Selective Interleukin-2 Inducible T-Cell Kinase (Itk) Inhibitors, Synthetic Route of 20029-52-1, the publication is Journal of Medicinal Chemistry (2011), 54(7), 2341-2350, database is CAplus and MEDLINE.

Interleukin-2 inducible T-cell kinase (Itk) plays a role in T-cell functions, and its inhibition potentially represents an attractive intervention point to treat autoimmune and allergic diseases. Herein we describe the discovery of a series of potent and selective novel inhibitors of Itk. These inhibitors were identified by structure-based design, starting from a fragment generated de novo, the 3-aminopyrid-2-one motif. Functionalization of the 3-amino group enabled rapid enhancement of the inhibitory activity against Itk, while introduction of a substituted heteroaromatic ring in position 5 of the pyridone fragment was key to achieving optimal selectivity over related kinases. A careful anal. of the hydration patterns in the kinase active site was necessary to fully explain the observed selectivity profile. The best mol. prepared in this optimization campaign, 7v, inhibits Itk with a K_i of 7 nM and has a good selectivity profile across kinases.

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, Synthetic Route of 20029-52-1.

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

Pacut, Ryszard published the artcileReduction of polyaromatic carboxylic acids with lithium in ethylenediamine and tetrahydrofuran, Quality Control of 20029-52-1, the publication is Polish Journal of Chemistry (1985), 59(4), 447-51, database is CAplus.

The use of large amounts of Li in the title reduction led to ring reduction without affecting the CO₂H group. Thus, treatment of 5 mmole 1-naphthoic acid with 50 mmole Li in H₂NCH₂CH₂NH₂-THF gave reduced naphthoic acid I. Reduction of 2-naphthoic acid with Li (1:5 molar ratio) gave hydronaphthoic acid II, whereas using (1:15 molar ratio) gave III (R = CO₂H, CHO). Five mmole 4-PhC₆H₄CO₂H reduced with 50 mmole Li gave benzoic acid IV.

Polish Journal of 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, Quality Control of 20029-52-1.

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

Duan, Jiang published the artcileDisilyl Bis(Secondary Amine)-Enabled Epoxy Ring-Opening and Silylotropic N → O Migration Leading to Low Dielectric Epoxy Copolymers, HPLC of Formula: 1761-71-3, the publication is Macromolecules (Washington, DC, United States) (2021), 54(14), 6947-6955, database is CAplus.

This work presents a strategy for fabricating low dielec. epoxy copolymers through copolymerizing bisphenol A diglycidyl ether with N,N’-disilyl bis(secondary amine)s, a series of difunctional silylamines synthesized by silylation of bis(secondary amine)s. A study on the model reaction of monoepoxy with monofunctional silylamines identified that the reaction proceeded smoothly in THF with Mg(ClO₄)₂ catalysis and mechanistically through sequential silylamine-induced epoxy ring-opening and silylotropic N → O migration, a process with favorable Gibbs free energy changes as confirmed by d. functional theory calculations The copolymers demonstrated remarkably low dielec. constants and dielec. losses due to the formation of the low-polarizable silyloxyl instead of the hydroxyl group in polymerization and the enlarged mol. free volume In addition, the copolymers showed desirable toughness, hydrophobicity, and thermal stability. As a tool to achieve these desirable features, the strategy developed in this work may find promising application in designing low dielec. epoxy resin materials for use in the microelectronic field.

Macromolecules (Washington, DC, United States) 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, HPLC of Formula: 1761-71-3.

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

Hodgson, Sabrina M. published the artcileReproducible Dendronized PEG Hydrogels via SPAAC Cross-Linking, Synthetic Route of 1353016-70-2, the publication is Biomacromolecules (2017), 18(12), 4054-4059, database is CAplus and MEDLINE.

A common issue with hydrogel formulations is batch-to-batch irreproducibility, originating from poorly-defined polymer precursors. Here, we report the use of dendritic polymer end-groups to address this issue and maintain reproducibility between batches of poly(ethylene glycol) (PEG) hydrogels. Specifically, we synthesized two end-functionalized PEG chains, one with azide-terminated first- and second-generation dendrons, and the other with strained cyclooctynes. The two complementary azide and alkyne polymers react via the Strain-Promoted Alkyne-Azide Cycoladdn. (SPAAC) to produce hydrogels quickly in the absence of addnl. reagents or catalyst, at low polymer concentrations Hydrogels made with first-generation dendrons gelled in minutes and exhibited a small degree of swelling when incubated in PBS buffer at 37°C, while hydrogels made from second-generation dendrons gelled in seconds with almost no swelling upon incubation at 37°C. In both cases, the hydrogels proved reproducible, resulting in identical Young’s Modulus (YM) values from different batches. The hydrogels prepared with second-generation dendrons were seeded with human mesenchymal stem cells (hMSCs), and showed high cell viability, as well as cell spreading over a two-week timeframe. These studies show that the SPAAC hydrogels are non-cytotoxic, and are capable of supporting cell growth.

Biomacromolecules 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

Babij, Nicholas R. published the artcileStereocontrolled Synthesis of Bicyclic Sulfamides via Pd-Catalyzed Alkene Carboamination Reactions. Control of 1,3-Asymmetric Induction by Manipulating Mechanistic Pathways, Safety of 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, the publication is Organic Letters (2014), 16(12), 3412-3415, database is CAplus and MEDLINE.

Arylmethyl and allylic cyclic sulfamides such as pyrroloisothiadiazinediones and pyridoisothiadiazinedione I [R = H, H₂C:CHCH₂; R¹ = Ph, 4-t-BuC₆H₄, 4-MeOC₆H₄, 4-PhCOC₆H₄, 2-MeC₆H₄, 1-cyclohexenyl, Me(CH₂)₇CH:CH; X = CH₂, CH₂CH₂; PMP = 4-MeOC₆H₄] were prepared in 43-89% yields and in 5:1-13:1 diastereoselectivities by intramol. alkene carboamination reactions of allyl-substituted heteroaryl sulfamides such as II (R = H, H₂C:CHCH₂; X = CH₂, CH₂CH₂) with aryl triflates R¹OTf [R¹ = Ph, 4-t-BuC₆H₄, 4-MeOC₆H₄, 4-PhCOC₆H₄, 2-MeC₆H₄, 1-cyclohexenyl, Me(CH₂)₇CH:CH] in the presence of Pd(OAc)₂ and the phosphine ligand CPhos III (Cy = cyclohexyl) in tert-butanol. The ligands of and conditions for palladium-catalyzed carboamination reactions may be tuned to favor either anti- and syn-aminopalladation reactions and thus to obtain different product diastereomers.

Organic Letters 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, Safety of 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine.

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

Thauvin, Cedric published the artcileMicrowave-assisted synthesis of self-assembling bi-functionalizable amphiphilic diblock copolymers, Application In Synthesis of 1353016-70-2, the publication is Journal of Drug Delivery Science and Technology (2021), 102255, database is CAplus.

Active biodegradable polymeric materials are a key area of investigation to develop new imaging and treatment modalities. In this study, we sought to develop tailor-made bi-functionalizable amphiphilic diblock copolymers (BFACs) bearing different reactive groups (e.g., azide, alkyne, maleimide, biotin) on both ends. Designed with a linear backbone constituted of poly (lactic acid), a hydrophobic biodegradable polyester, and poly (ethylene glycol), a hydrophilic biocompatible polymer, BFACs can self-assemble in aqueous media. They are synthesized using a straightforward two-step process: a microwave-assisted ring-opening polymerization followed by a Steglich esterification. BFACs are able to keep their micellar state after the functionalization of their reactive groups via covalent linking or strong interactions with different fluorescent dyes. Interestingly, formation of BFACs-based micelles and their double labeling can be performed in one step. Finally, the uptake of functionalized BFACs-based micelles in the cytoplasmic compartments of MCF-7 cells is observed, thereby illustrating the potential of BFACs to be an easy-to-use tool towards fast development of nanoconstructs for therapy, imaging or theranostics.

Journal of Drug Delivery Science and Technology 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 C6H11BF3KO, Application In Synthesis of 1353016-70-2.

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