Day: March 9, 2021

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Insect muscarinic acetylcholine receptor: Pharmacological and toxicological profiles of antagonists and agonists

The insect muscarinic acetylcholine receptor (mAChR) is evaluated as a potential target for insecticide action. The mammalian M2/M4-selective antagonist radioligand [3H]AF-DX 384 (a pirenzepine analogue) binds to Drosophila mAChR at a single high-affinity site identical to that for the nonselective antagonist [3H]quinuclidinyl benzilate (QNB) and with a pharmacological profile distinct from that of all mammalian mAChR subtypes. Three nonselective antagonists (QNB, scopolamine, and atropine) show the highest affinity (Ki = 0.5-2.4 nM) at the Drosophila target, and AF-DX 384 and M3-selective 4-DAMP (dimethyl-4-(diphenylacetoxy)piperidinium iodide) rank next in potency (Ki = 5-18 nM). Eleven muscarinic antagonists generally exhibit higher affinity than eight agonists. On injection into houseflies, the antagonists 4-DAMP and (S)-(+)-dimethindene produce suppressed movement, the agonist (methyloxadiazolyl)quinuclidine causes knockdown and tremors, and all of them inhibit [3H]-QNB binding ex vivo, indicating possible mAChR-mediated intoxication. The insect mAChR warrants continuing study in lead generation to discover novel insecticides.

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Quinuclidine – Wikipedia,
Quinuclidine | C7H62N | ChemSpider

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Metabolomics responses of Bambusa pervariabilis ¡Á Dendrocalamopsis grandis varieties to Biotic (pathogenic fungus) stress

Bambusa pervariabilis ¡Á Dendrocalamopsis grandis blight, caused by Arthrinium phaeospermum, is one of the most common and serious diseases in bamboo and occurs in the newly born twigs. Bamboo has suffered large dead areas, including more than 3000 hm2, which greatly threatens the process of returning farmlands to forests and the construction of ecological barriers. To identify differential metabolites and metabolic pathways associated with B. pervariabilis ¡Á D. grandis to A. phaeospermum, ultra-performance liquid chromatography (UPLC) and quadrupole-time of flight (Q-TOF) Mass Spectrometry (MS) combined with a data-dependent acquisition method was used to analyse the entire sample spectrum. In total, 13223 positive ion peaks and 10616 negative ion peaks were extracted. OPLS-DA and several other analyses were performed using the original data. The OPLS-DA models showed good quality and had strong predictive power, indicating clear trends in the analyses of the treatment and control groups. Clustering and KEGG pathway analyses were used to screen the differential metabolites in the treatment and control groups from the three B. pervariabilis ¡Á D. grandis varieties and reflected their metabolic responses induced by A. phaeospermum infection. The results showed that the three B. pervariabilis ¡Á D. grandis varieties mode showed significant changes in the following six resistance-related metabolites after A. phaeospermum invasion in positive and negative ion modes: proline, glutamine, dictamnine, apigenin 7-O-neohesperidoside, glutamate, and cis-Aconitate. The following four main metabolic pathways are involved: Arginine and proline metabolism, Glyoxylate and dicarboxylate metabolism, Biosynthesis of alkaloids derived from shikimate pathway, and Flavone and flavonol biosynthesis. This study lays a foundation for the later detection of differential metabolites and metabolic pathways for targeting, and provides a theoretical basis for disease-resistant breeding and the control of B. pervariabilis ¡Á D. grandis blight.

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Quinuclidine – Wikipedia,
Quinuclidine | C7H68N | ChemSpider

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Nickel in Photocatalysis

Robust methods to forge C-C bonds selectively are treasured by the chemical community because of the inherent value of such processes in the convergent construction of complex molecules and the notorious challenges associated with creating such linkages. The advent of cross-coupling technologies (e.g., Suzuki, Negishi, and Heck processes) has revolutionized how synthetic chemists establish C(sp2)-C(sp2) bonds. However, the mechanistic features that make these transition-metal-catalyzed processes ideal for this type of transformation are the same ones that limit their abilities to involve C(sp3)-hybridized species. In this chapter, a recently developed solution to the underlying challenge of engaging C(sp3)-hybridized nucleophiles in cross coupling is outlined: nickel/photoredox dual catalysis. By proceeding through radical intermediates, the enthalpic penalty for two-electron transmetalation can be side-stepped, and cross coupling can proceed under mild, functional-group-tolerant conditions. Several variants of this dual catalytic process are presented which, taken together, demonstrate the breadth and scope of this new cross-coupling paradigm.

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Quinuclidine – Wikipedia,
Quinuclidine | C7H66N | ChemSpider

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Receptor agonist activity is not a requirement for muscarinic antinociception

The analgesic effects of a series of muscarinic agonists were investigated by use of the mouse acetic acid writhing, gridshock, hot-plate and tail-flick tests. The compounds tested were oxotremorine, pilocarpine, arecoline, aceclidine, RS86 and four 3-3(substituted-1,2,5-thiadiazol-4-yl)- 1,2,5,6-tetrahydro-1-methyl pyridines (substituted TZTP), these being propoxy-TZTP, 3-Cl-propylthio-TZTP, xanomeline (hexyloxy-TZTP) and hexylthio- TZTP. These agonists were also assayed for their ability to displace [3H]oxotremorine-M and [3H]pirenzepine binding and for their functional selectivity at pharmacologic M1, M2 and M3 receptors. These compounds all produced dose-dependent antinociceptive effects in all of the mouse analgesia tests. The effects of oxotremorine in the writhing test were fully antagonized by the muscarinic antagonist scopolamine (0.1 mg/kg), but only partially antagonized by methscopolamine (10 mg/kg) and unaffected by the opioid antagonist naltrexone. 3-Cl-propylthio-TZTP and propoxy-TZTP had virtually no effect at the M1 receptor subtype as measured by the human m1 clone expressed in baby hamster kidney cells or the rabbit vas deferens assay. These compounds, however, were more potent in the analgesia tests than the selective M1 agonists xanomeline and hexylthio-TZTP. These data suggest that muscarinic analgesia is mediated by central muscarinic receptors. However, activity at the M1 receptor subtype is not a requirement for antinociceptive activity.

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Quinuclidine – Wikipedia,
Quinuclidine | C7H83N | ChemSpider

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Discovery of highly potent and selective type I B-Raf kinase inhibitors

A series of pyrazolo[1,5-alpha]pyrimidine analogs has been prepared and found to be potent and selective B-Raf inhibitors. Molecular modeling suggests they bind to the active conformation of the enzyme.

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Quinuclidine – Wikipedia,
Quinuclidine | C7H29N | ChemSpider

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Structure-based discovery of prescription drugs that interact with the norepinephrine transporter, NET

The norepinephrine transporter (NET) transports norepinephrine from the synapse into presynaptic neurons, where norepinephrine regulates signaling pathways associated with cardiovascular effects and behavioral traits via binding to various receptors (e.g., beta2-adrenergic receptor). NET is a known target for a variety of prescription drugs, including antidepressants and psychostimulants, and may mediate off-target effects of other prescription drugs. Here, we identify prescription drugs that bind NET, using virtual ligand screening followed by experimental validation of predicted ligands. We began by constructing a comparative structural model of NET based on its alignment to the atomic structure of a prokaryotic NET homolog, the leucine transporter LeuT. The modeled binding site was validated by confirming that known NET ligands can be docked favorably compared to nonbinding molecules. We then computationally screened 6,436 drugs from the Kyoto Encyclopedia of Genes and Genomes (KEGG DRUG) against the NET model. Ten of the 18 high-scoring drugs tested experimentally were found to be NET inhibitors; five of these were chemically novel ligands of NET. These results may rationalize the efficacy of several sympathetic (tuaminoheptane) and antidepressant(tranylcypromine) drugs, as well as side effects of diabetes (phenformin) and Alzheimer’s (talsaclidine) drugs. The observations highlight the utility of virtual screening against a comparative model, even when the target shares less than 30% sequence identity with its template structure and no known ligands in the primary binding site.

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Quinuclidine – Wikipedia,
Quinuclidine | C7H80N | ChemSpider

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QUINUCLIDINES SUBSTITUTED BENTODIOXINE CARBOXAMIDES FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES

The invention provides the malate salt of compounds of Formula I, wherein X is malate salt, including D- or L-; wherein A is (a), wherein B is (b) or pharmaceutical composition, racemic mixture, or pure enantiomer thereof. The compounds of Formula I are useful to treat diseases or conditions in which alpha7 is known to be involved.

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Quinuclidine – Wikipedia,
Quinuclidine | C7H130N | ChemSpider

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Actionable perturbations of damage responses by TCL1/ATM and epigenetic lesions form the basis of T-PLL

T-cell prolymphocytic leukemia (T-PLL) is a rare and poor-prognostic mature T-cell malignancy. Here we integrated large-scale profiling data of alterations in gene expression, allelic copy number (CN), and nucleotide sequences in 111 well-characterized patients. Besides prominent signatures of T-cell activation and prevalent clonal variants, we also identify novel hot-spots for CN variability, fusion molecules, alternative transcripts, and progression-associated dynamics. The overall lesional spectrum of T-PLL is mainly annotated to axes of DNA damage responses, T-cell receptor/cytokine signaling, and histone modulation. We formulate a multi-dimensional model of T-PLL pathogenesis centered around a unique combination of TCL1 overexpression with damaging ATM aberrations as initiating core lesions. The effects imposed by TCL1 cooperate with compromised ATM toward a leukemogenic phenotype of impaired DNA damage processing. Dysfunctional ATM appears inefficient in alleviating elevated redox burdens and telomere attrition and in evoking a p53-dependent apoptotic response to genotoxic insults. As non-genotoxic strategies, synergistic combinations of p53 reactivators and deacetylase inhibitors reinstate such cell death execution.

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Quinuclidine – Wikipedia,
Quinuclidine | C7H175N | ChemSpider

Let¡¯s face it, organic chemistry can seem difficult to learn. Especially from a beginner¡¯s point of view. Like 123536-14-1, Name is (R)-3-Aminoquinuclidine dihydrochloride. In a document type is Article, introducing its new discovery., Product Details of 123536-14-20

Drugs, leads, and drug-likeness: an analysis of some recently launched drugs.

An analysis of the origins of recently launched drugs reveals that most were derived by modification of known drug structures or from lead structures obtained from the scientific literature. High-throughput screening did not have a significant impact on the derivation of these drugs. The drug structures are very closely related to their leads.

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Quinuclidine – Wikipedia,
Quinuclidine | C7H79N | ChemSpider

Let¡¯s face it, organic chemistry can seem difficult to learn. Especially from a beginner¡¯s point of view. Like 123536-14-1, Name is (R)-3-Aminoquinuclidine dihydrochloride. In a document type is Article, introducing its new discovery., Product Details of 123536-14-19

Quantitative Evaluation of the Reactivity of Alkylating Agents

A sensitive and reproducible method for quantitative evaluation of the relative reactivities of alkylating agents was developed, based on competitive alkylation.The method is superior to the known calorimetric methods.The reactivities of the agents could also be correlated with the 13C chemical shifts of the alpha-methylene.The method was successfully applied for the ranking of “soft” alkylating agents of low reactivity. – Keywords: Alkylating Agents, Soft Drugs, NMR Spectra, Competitive Alkylation, Soft Quaternary Salts

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Quinuclidine – Wikipedia,
Quinuclidine | C7H47N | ChemSpider