Category: 827-61-2

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Design, Synthesis, and Neurochemical Evaluation of 5-(3-Alkyl-1,2,4-oxadiazol-5-yl)-1,4,5,6-tetrahydropyrimidines as M1 Muscarinic Receptor Agonists

A series of 5-(3-alkyl-1,2,4-oxadiazol-5-yl)-1,4,5,6-tetrahydropyrimidines (7a-h) was synthesized for biological evaluation as selective agonists for M1 receptors coupled to phosphoinositide (PI) metabolism in the central nervous system.Each ligand bound with high affinity to muscarinic receptors from rat brain as measured by inhibition of <3H>-(R)-quinuclidinyl benzilate (<3H>-(R)-QNB) binding. 5-(3-Methyl-1,2,4-oxadiazol-5-yl)-1,4,5,6-tetrahydropyrimidine trifluoroacetate (CDD-0098-J; 7a)displayed high affinity (IC50 = 2.7 +/- 0.69 muM) and efficacy at muscarinic receptors coupled to PI metabolism in the rat cortex and hippocampus .Increasing the length of the alkyl substituent increased affinity for muscarinic receptors yet decreased activity in PI turnover assays.The hippocampal PI response of 7a was blocked by lower concentrations of pirenzepine (8) or by higher concentrations of either AF-DX 116 (9) or p-fluorohexahydrosiladifenidol (10), suggesting that a low concentrations 7a selectively stimulates PI turnover through M1 receptors.

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Quinuclidine – Wikipedia,
Quinuclidine | C7H53N | ChemSpider

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95. Inductive Charge Dispersal in Quinuclidinium Ions. Polar Effects, Part 13

Inductive charge dispersal to the alpha-, beta-, and gamma-positions of the solvated quinuclidinium ion has been examined by comparing the pKa and the derived inductivities rho1 of several 2-, 3- and 4-substituted quinuclidinium perchlorates 4, 5, and 6, respectively.The same inductivity is observed at the practically equidistant beta- and gamma-positions.It, therefore, appears that polar substituent effects are transmitted directly through the molecule.As expected, inductivity is considerably higher at the alpha-positions where through-bond and direct induction coincide.The fact that the pKa of all three series of salts correlate linearly with each other points to the common nature of these inductive electron displacements.

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One of the major reasons for studying chemical kinetics is to use measurements of the macroscopic properties of a system, Computed Properties of C9H15NO2, such as the rate of change in the concentration of reactants or products with time.In a article, authors is Montes-Mico, Robert, mentioned the application of Computed Properties of C9H15NO2, Name is Quinuclidin-3-yl acetate, molecular formula is C9H15NO2

Pharmacological strategies for presbyopia correction

Purpose: To summarize the pharmacological strategies that are being explored for presbyopia correction. Methods: The review concentrates on pharmacologically induced pupillary miosis to increase depth-of-focus and lens softening or other measures to restore active accommodation. Results: Several studies suggest that near vision improves and distance vision is unaffected for many hours after either monocular or binocular instillation of any one of several drug combinations that cause miosis. Unfortunately, in most studies, measurements were limited to photopic visual acuity for near and distance vision, whereas it is anticipated that pupil constriction may have adverse effects on mesopic and scotopic vision. It is not clear whether improved near vision was due entirely to increased depth-of-focus, or whether, for example, a drug-induced myopic shift in refraction was also involved. Currently, no study has provided direct evidence for drug-induced restoration/enhancement of true accommodation involving an ocular power change. Conclusions: Although it is possible that, in the future, pharmacological drops may offer a safe and reliable solution for presbyopia correction, more evidence of their effectiveness and limitations is required.

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In vitro muscarinic activity of spiromuscarones and related analogs

The cholinergic hypothesis of Alzheimer’s disease suggests that cholinergic agonists may have therapeutic potential for treating the attendant memory deficits of the disease. As part of a program aimed at preparing metabolically stable, nonquaternary analogs of muscarone, 1-oxa- 2,8-dimethyl-8-azaspiro[4.5]decan-3-one, 2a, and related analogs have been synthesized and their in vitro muscarinic activity evaluated. The synthetic strategy in the formation of the 1-spiro[4.5]decan-3-one ring system of 2a involved cyclization of the diol 4 in the presence of Nafion-Hg. The spiromuscarone 2a was found to displace [3H]Oxo-M binding with a K(i) value of 7 nM. Affinities of the oxime and hydrazone analogs of 2a were lower than 2a. The compounds in these series were partial muscarinic agonists as demonstrated by stimulation of phosphatidyl inositol hydrolysis assay, with 2a showing the highest intrinsic activity (60% as compared with carbachol). The results from this study indicate that an exo double bond at the C-3 position is essential for the receptor binding.

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Quinuclidine – Wikipedia,
Quinuclidine | C7H90N | ChemSpider

One of the major reasons for studying chemical kinetics is to use measurements of the macroscopic properties of a system, COA of Formula: C9H15NO2, such as the rate of change in the concentration of reactants or products with time.In a article, mentioned the application of 827-61-2, Name is Quinuclidin-3-yl acetate, molecular formula is C9H15NO2

A practical chemoenzymatic process to access (R)-quinuclidin-3-ol on scale

(¡À)-3-Butyryloxyquinuclidinium butyrate 6 (2 M, 571 g/L), prepared from (¡À)-quinuclidin-3-ol 1 and butyric anhydride, undergoes enantioselective hydrolysis by an Aspergillus melleus protease {1.0% (w/v)} in water in the presence of Ca(OH)2 to keep the reaction at pH 7 and trap butyric acid that is introduced as part of (¡À)-6 and generated by the enzymatic hydrolysis. After a 24 h period, extraction with n-heptane provides (R)-quinuclidin-3-yl butyrate 5a, which, on methanolysis with Na2CO3, is converted into (R)-1, a common pharmacophore of neuromodulators acting on muscarinic receptors, in 96% ee and 42% overall yield from (¡À)-1. The unwanted antipode (S)-1, which is extracted into n-butanol and purified via its hydrochloride salt in 89% ee and 40% overall yield from (¡À)-1, can be racemized by the catalysis of Raney Co at 140C under an atmosphere of H2 (5 kg/cm2) to regenerate (¡À)-1 in 97% yield.

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Quinuclidine | C7H75N | ChemSpider

In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum.In a patent, Computed Properties of C9H15NO2, name is Quinuclidin-3-yl acetate, introducing its new discovery. Computed Properties of C9H15NO2

Aceclidine and pilocarpine interact differently with muscarinic receptor in isolated rabbit iris muscle

The relationship between muscarinic receptor affinity states and the contractile response to the muscarinic agonists carbachol, aceclidine, and pilocarpine, has been examined in the isolated rabbit iris muscle. Contraction of the iris muscle by carbachol and aceclidine was more potent and/or more efficacious than the response to pilocarpine. Analysis of [3H]- Quinuclidinyl benzilate (QNB) binding showed that while both carbachol and aceclidine bound to high- and low-affinity forms of the muscarinic receptor, pilocarpine bound to one affinity state. The efficacy of carbachol and aceclidine to stimulate contraction of the iris muscle was consistent with receptor occupancy theory only when considering the low-affinity state of the muscarinic receptor, and activation of the low-affinity rather than high-affinity binding state of the receptor is likely to mediate the contraction of iris muscle. Therefore, the typical anti-glaucoma muscarinic agonists aceclidine and pilocarpine may interact differently with their target receptors in isolated rabbit iris muscle.

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Drug release from porous matrixes based on natural polymers

Background: This review provides a report on recent advances in the field of drug release from matrixes made of natural polymers. Herein, the properties of natural polymers such as proteins and polysaccharides are discussed in general. Selected detailed examples of drug release profiles from biopolymer matrixes have also been collected from scientific literature and practical work, and commented on. In this review, the most common natural polymers, i.e. collagen, elastin, chitosan, hyaluronic acid and sodium alginate have been discussed as biopolymers that can be potentially applied in drug delivery systems. Methodology: The most rapidly developing field of the biomaterials science is the one dealing with their application as matrixes in drug release systems. Such systems show numerous advantages when compared to conventional ones. They improve medical treatment efficiency due to the fact that drugs are placed directly into the infected part. Moreover, the drug release systems reduce toxic reactions because the drug does not pass through the body and, as a result, does not affect the healthy tissues. Such systems also improve the patient?s comfort during the treatment. Result: Biocompatibility, bioresorbability and non-toxicity are the significant properties characteristic for natural polymers. Natural polymers can be used to obtain biomaterials which can further find their applications in the production of bones or soft tissues implants as well as dressing materials placed on damaged skin. Nevertheless, the disadvantages of biomaterials made of natural polymers, e.g., high solubility and low thermal stability, limit the range of their potential applications. Therefore, it is necessary to modify material properties by carrying out the cross-linking process. Conclusion: Recently, a rapidly growing interest in the use of porous materials as controlled drug delivery matrixes has been observed since they present several positive features. The drug release from polymeric matrixes is based on the carrier degradation process which depends on dissolving and diffusion processes. The selection of a polymeric matrix depends on its compatibility with the drug as well as the manufacturing process which needs to be considered. The proper adjustment of the drug release rate is necessary to obtain the best results during medical treatment. Numerous classes of hydrophilic as well as hydrophobic drugs can be released from polymeric matrixes which is beneficial to medical treatment. The research of different drug release systems has already been carried out, and the results can be found in scientific literature.

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Quinuclidine | C7H65N | ChemSpider

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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

Let¡¯s face it, organic chemistry can seem difficult to learn. Especially from a beginner¡¯s point of view. Like category: quinuclidine, Name is Quinuclidin-3-yl acetate. In a document type is Article, introducing its new discovery., category: quinuclidine

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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Correlation between pKa and reactivity of quinuclidine-based catalysts in the Baylis-Hillman reaction: Discovery of quinuclidine as optimum catalyst leading to substantial enhancement of scope

The reactivity of a variety of quinuclidine-based catalysts in the Baylis-Hillman reaction has been examined, and a straightforward correlation between the basicity of the base and reactivity has been established, without exception. The following order of reactivity was established with pKa’s of the conjugate acids (measured in water) given in parentheses: quinuclidine (11.3), 3-hydroxyquinuclidine (9.9), DABCO (8.7), 3-acetoxyquinuclidine (9.3), 3-chloroquinuclidine (8.9), and quinuclidinone (7.2). The higher than expected reactivity of DABCO, based on its pKa, was analyzed by comparing the relative basicity of DABCO and 3-acetoxyquinuclidine in DMSO. It was found that in aprotic solvent, DABCO was 0.6 pKa units more basic than 3-acetoxyquinuclidine, thus establishing a direct link between pKa of the amine and its reactivity. In contrast to previous literature work that reported the contrary, quinuclidine, which has the highest pKa, was found to be the most active catalyst. The reaction profile with quinuclidine showed significant autocatalysis, which suggested that the presence of proton donors might further enhance rates. Thus, a series of additives bearing polar X-H bonds were investigated and it was found that methanol, triethanolamine, formamide, and water all provided additional acceleration. Methanol was found to be optimum, and the powerful combination of quinuclidine with methanol was tested with a host of aldehydes and Michael acceptors. Not only were the reactions more efficient and faster than previously reported, but now new substrates that were previously unreactive could be employed. Notable examples include the use of acetylenic aldehydes and the employment of vinyl sulfones, acrylamides, delta-lactones, and even alpha,beta-unsaturated esters bearing a beta-substituent.

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