Heterocyclic Building Blocks-Quinuclidine

Wolfgang, Josh D. published the artcileNon-isocyanate Polyurethanes from 1,1′-Carbonyldiimidazole: A Polycondensation Approach, COA of Formula: C13H26N2, the publication is Macromolecular Rapid Communications (2021), 42(13), 2100163, database is CAplus and MEDLINE.

1,1′-Carbonyldiimidazole (CDI) provides a platform to generate high mol. weight polyurethanes from industrially relevant diols and diamines. CDI, which is described in the literature for its use in amidation and functionalization reactions, enables the production of well-defined and stable polyurethane precursors, thus eliminating the need for isocyanates. Herein, the functionalization of 1,4-butanediol with CDI yields an electrophilic biscarbamate, bis-carbonylimidazolide (BCI), which is suitable for further step-growth polymerization in the presence of amines. Elevated reaction temperatures enable the solvent-, catalyst-, and isocyanate-free polycondensation reaction between the BCI monomer and various diamines. The thermoplastic polyurethanes produced from this reaction demonstrate high thermal stability, tunable glass transition temperatures based on incorporation of flexible polyether segments, and mech. ductile thin films. CDI functionalized diols will allow the preparation of diverse polyurethanes without the use of isocyanate-containing monomers.

Macromolecular Rapid Communications 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 C10H12O5, COA of Formula: C13H26N2.

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

Liu, Xin published the artcileIndirect reduction of CO₂ and recycling of polymers by manganese-catalyzed transfer hydrogenation of amides, carbamates, urea derivatives and polyurethanes, Application of 4,4-Diaminodicyclohexyl methane, the publication is Chemical Science (2021), 12(31), 10590-10597, database is CAplus and MEDLINE.

A manganese pincer complex as a versatile catalyst for the transfer hydrogenation of amides, carbamates, urea derivatives and even polyurethanes leading to the corresponding alcs., amines and methanol as products were reported. Since these compound classes can be prepared using CO₂ as a C1 building block the reported reaction represents an approach to the indirect reduction of CO₂. Notably, these are the first examples on the reduction of carbamates and urea derivatives as well as on the C-N bond cleavage in amides by transfer hydrogenation. The general applicability of this methodol. is highlighted by the successful reduction of 12 urea derivatives, 26 carbamates and 11 amides. The corresponding amines, alcs. and methanol were obtained in good to excellent yields up to 97%. Furthermore, polyurethanes were successfully converted which represents a viable strategy towards a circular economy. Based on control experiments and the observed intermediates a feasible mechanism was proposed.

Chemical Science 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 of 4,4-Diaminodicyclohexyl methane.

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

Rajagopalan, Narayanan published the artcileDegradation mechanisms of amine-cured epoxy novolac and bisphenol F resins under conditions of high pressures and high temperatures, Quality Control of 1761-71-3, the publication is Progress in Organic Coatings (2021), 106268, database is CAplus.

Projections of continued growth in the global hydrocarbon demand and fast depleting resources push the oil and gas industry to explore and produce in geol. formations with abnormal high pressures and temperatures, so-called HPHT conditions. In the present study, the largely unexplored degradation mechanisms for amine-cured epoxy novolac (EN) and bisphenol F (BPF) epoxy resins are investigated at lower limits of HPHT. Using a batch-like reactor encompassing the three relevant phases (a gas mixture of nitrogen and carbon dioxide, a hydrocarbon phase of aromatic para-xylene, and an artificial seawater phase), the conditions of high pressures and high temperatures were simulated. The EN and BPF coated steel panels were placed inside the batch reactor. In the gas phase-exposed zone, both EN and BPF remained essentially intact with no major defects. However, due to para-xylene uptake that resulted in a free volume increase (i.e. lowering of the glass transition temperature), the hydrocarbon-exposed zones of EN and BPF were partly covered by an oxide of iron, the origin of which was found to be diffusion of anodically-dissolved iron from the steel-coating interface. The enhanced resin chain mobility at the hydrocarbon-seawater interphase allowed higher rates of diffusion of seawater ions to the steel-coating interface with clear signs of coating degradation Finally, the seawater phase induced small blisters in the EN coating, whereas for BPF, a complete loss of adhesion between the coating and the substrate was observed Simulation of Rapid Gas Decompression (RGD), uncovered the role of RGD in the iron oxide formation process for both EN and BPF coatings. In summary, when compared to BPF, the EN network showed superior performance under conditions of HPHT.

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 C13H26N2, Quality Control of 1761-71-3.

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

Yang, Xiu published the artcileEnhanced reflection chiroptical effect of planar anisotropic chiral metamaterials placed on the interface of two media, Related Products of quinuclidine, the publication is Chinese Physics B (2020), 29(10), 107303, database is CAplus.

The strong chiroptical effect is highly desirable and has a wide range of applications in biosensing, chiral catalysis, polarization tuning, and chiral photo detection. In this work, we find a simple method to enhance the reflection CD (CDR) by placing the planar anisotropic chiral metamaterials (i.e., Z-shaped PACMs) on the interface of two media (i.e., Z-PCMI) with a large refractive index difference. The maximum reflection CDR from the complex system can reach about 0.840 when the refractive index is set as ntop = 4.0 and nbottom = 1.49, which is approx. three times larger than that of placing the Z-shaped PACMs directly on the substrate (i.e., Z-PCMS). While the min. reflection CDR is 0.157 when the refractive index is set as ntop = 1.0 and nbottom = 1.49. So we can get a large available range of reflection CDR from -0.840 to -0.157. Meanwhile, the transmission CDT remains unchanged with the refractive index ntop increment. Our in-depth research indicates that the large reflection CDR is derived from the difference of non-conversion components of the planar anisotropic chiral metamaterials’ reflection matrixes. In short, we provide a simple and practical method to enhance the chiroptical effect by changing the refractive index difference between two media without having to design a complex chiral structure.

Chinese Physics 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 C10H14N2O, Related Products of quinuclidine.

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

Tian, Zong-Qiang published the artcilePotent Cytotoxic C-11 Modified Geldanamycin Analogues, Synthetic Route of 795299-77-3, the publication is Journal of Medicinal Chemistry (2009), 52(10), 3265-3273, database is CAplus and MEDLINE.

17-Allylamino-17-demethoxygeldanamycin (17-AAG) inhibits the activity of Hsp90, an important target for treatment of cancers. In an effort to identify analogs of geldanamycin (GDM) with properties superior to those of 17-AAG, we synthesized C-11 modified derivatives of GDM including ethers, esters, carbazates, ketones, and oximes, and measured their affinity for Hsp90 and their ability to inhibit growth of human cancer cells. In accordance with crystal structures reported for complexes of GDMs with Hsp90, bulky groups attached to C-11 interfered with Hsp90 binding while smaller groups such as 11-O-Me allowed Hsp90 binding. In addition, these analogs also showed in vitro cytotoxicity against human cancer cell lines. Esterfication of the 11-OH of 17-AAG eliminated Hsp90 binding in vitro. The readily hydrolyzed esters acted as prodrugs during the measurement of cytotoxicity. Thus, during these experiments, the esters were hydrolyzed, releasing 17-AAG. Several 11-O-methyl-17-alkylaminogeldanamycin analogs were identified with improved potency relative to 17-AAG.

Journal of Medicinal Chemistry published new progress about 795299-77-3. 795299-77-3 belongs to quinuclidine, auxiliary class Azetidine,Amine, name is 2-(Azetidin-1-yl)ethanamine, and the molecular formula is C8H16O2, Synthetic Route of 795299-77-3.

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

Jia, Li published the artcileSynthesis and antibacterial evaluation of novel 11-O-aralkylcarbamoyl-3-O-descladinosylclarithromycin derivatives, Application In Synthesis of 20029-52-1, the publication is Bioorganic & Medicinal Chemistry Letters (2018), 28(14), 2471-2476, database is CAplus and MEDLINE.

A series of novel 11-O-aralkylcarbamoyl-3-O-descladinosylclarithromycin derivatives were designed, synthesized and evaluated for their in vitro antibacterial activity. The results showed that the majority of the target compounds displayed potent activity against erythromycin-susceptible S. pyogenes, erythromycin-resistant S. pneumoniae A22072 expressing the mef gene and S. pneumoniae AB11 expressing the mef and erm genes. Besides, most of the target compounds exhibited moderate activity against erythromycin-susceptible S. aureus ATCC25923 and B. subtilis ATCC9372. Title compounds exert favorable antibacterial activity against erythromycin-susceptible S. pyogenes with the MIC values of 0.015-0.125 μg/mL. Furthermore, title compounds showed superior activity against erythromycin-resistant S. pneumoniae A22072 with the MIC values of 0.25-0.5 μg/mL. Addnl., compound c was the most effective against all the erythromycin-resistant S. pneumoniae strains (A22072, B1 and AB11), exhibiting 8-, 8- and 32-fold more potent activity than clarithromycin, resp.

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 C13H16O2, Application In Synthesis of 20029-52-1.

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

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

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

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