Tag: M.W:100-200

Related Products of 20859-23-8. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: (S)-2-Bromosuccinic acid, is researched, Molecular C4H5BrO4, CAS is 20859-23-8, about Stereoselective total synthesis of obolactones and 7′,8′-dihydroobolactones. Author is Saini, Deepak; Kumar, Praveen; Fernandes, Rodney A..

A concise stereoselective total synthesis of two diastereomeric obolactones and 7′,8′-dihydroobolactones has been achieved using a metal-free catalytic δ-hydroxyalkynone rearrangement, which could provide the required dihydro-γ-pyrone moiety. The desired first stereogenic center was installed through the chiral pool material, L-aspartic acid. Next, the allylation reaction was strategically utilized to provide the requisite olefin bond for the intended ring-closing metathesis, allowing the installation of the remaining dihydro-α-pyrone moiety in the natural products. It also enabled the targeting of both dihydro-α-pyrone diastereomers. Thus, the first stereoselective total synthesis of (+)-7′,8′-dihydroobolactone was accomplished, establishing its structure and absolute configuration.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

Fields, Ashley M.; Welle, Kevin; Ho, Elaine S.; Mesaros, Clementina; Susiarjo, Martha published the article 《Vitamin B6 deficiency disrupts serotonin signaling in pancreatic islets and induces gestational diabetes in mice》. Keywords: vitamin B6 deficiency gestational diabetes serotonin pancreatic islets signaling.They researched the compound: 4-Hydroxyquinoline-2-carboxylic Acid( cas:492-27-3 ).Category: copper-catalyst. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:492-27-3) here.

In pancreatic islets, catabolism of tryptophan into serotonin and serotonin receptor 2B (HTR2B) activation is crucial for β-cell proliferation and maternal glucose regulation during pregnancy. Factors that reduce serotonin synthesis and perturb HTR2B signaling are associated with decreased β-cell number, impaired insulin secretion, and gestational glucose intolerance in mice. Albeit the tryptophan-serotonin pathway is dependent on vitamin B6 bioavailability, how vitamin B6 deficiency impacts β-cell proliferation during pregnancy has not been investigated. In this study, we created a vitamin B6 deficient mouse model and investigated how gestational deficiency influences maternal glucose tolerance. Our studies show that gestational vitamin B6 deficiency decreases serotonin levels in maternal pancreatic islets and reduces β-cell proliferation in an HTR2B-dependent manner. These changes were associated with glucose intolerance and insulin resistance, however insulin secretion remained intact. Our findings suggest that vitamin B6 deficiency-induced gestational glucose intolerance involves addnl. mechanisms that are complex and insulin independent.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 4-Hydroxyquinoline-2-carboxylic Acid(SMILESS: O=C(C1=NC2=CC=CC=C2C(O)=C1)O,cas:492-27-3) is researched.Synthetic Route of C9H8N2. The article 《Kynurenine pathway metabolites in cerebrospinal fluid and blood as potential biomarkers in Huntingtons disease》 in relation to this compound, is published in Journal of Neurochemistry. Let’s take a look at the latest research on this compound (cas:492-27-3).

Converging lines of evidence from several models, and post-mortem human brain tissue studies, support the involvement of the kynurenine pathway (KP) in Huntingtons disease (HD) pathogenesis. Quantifying KP metabolites in HD biofluids is desirable, both to study pathobiol. and as a potential source of biomarkers to quantify pathway dysfunction and evaluate the biochem. impact of therapeutic interventions targeting its components. In a prospective single-site controlled cohort study with standardised collection of cerebrospinal fluid (CSF), blood, phenotypic and imaging data, we used high-performance liquid-chromatog. to measure the levels of KP metabolites-tryptophan, kynurenine, kynurenic acid, 3-hydroxykynurenine, anthranilic acid and quinolinic acid-in CSF and plasma of 80 participants (20 healthy controls, 20 premanifest HD and 40 manifest HD). We investigated short-term stability, intergroup differences, associations with clin. and imaging measures and derived sample-size calculation for future studies. Overall, KP metabolites in CSF and plasma were stable over 6 wk, displayed no significant group differences and were not associated with clin. or imaging measures. We conclude that the studied metabolites are readily and reliably quantifiable in both biofluids in controls and HD gene expansion carriers. However, we found little evidence to support a substantial derangement of the KP in HD, at least to the extent that it is reflected by the levels of the metabolites in patient-derived biofluids.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

Trepci, Ada; Sellgren, Carl M.; Paalsson, Erik; Brundin, Lena; Khanlarkhani, Neda; Schwieler, Lilly; Landen, Mikael; Erhardt, Sophie published an article about the compound: 4-Hydroxyquinoline-2-carboxylic Acid( cas:492-27-3,SMILESS:O=C(C1=NC2=CC=CC=C2C(O)=C1)O ).Formula: C10H7NO3. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:492-27-3) through the article.

The kynurenine pathway of tryptophan degradation produces several neuroactive metabolites such as kynurenic acid (KYNA), quinolinic acid (QUIN), and picolinic acid (PIC) thought to be involved in the pathophysiol. of psychosis, major depression, and suicidal behavior. Here, we analyzed cerebrospinal fluid (CSF) concentrations of tryptophan, kynurenine, KYNA, QUIN, and PIC utilizing ultra-performance liquid chromatog. – tandem mass spectrometry system (UPLC-MS/MS) in persons with bipolar disorder (n = 101) and healthy controls (n = 80) to investigate if the metabolites correlated with depressive symptoms or to the history of suicidal behavior. Furthermore, we analyzed if genetic variants of the enzyme amino-β-carboxymuconate-semialdehyde-decarboxylase (ACMSD) were associated with the CSF concentrations of PIC and QUIN. We found that CSF KYNA and PIC concentrations, as well as the kynurenine/tryptophan ratio were increased in bipolar disorder compared with controls. CSF PIC concentrations were lower in subjects with a history of suicidal behavior than those without, supporting the hypothesis that low CSF PIC is a marker of vulnerability for suicidality. Bipolar subjects taking antidepressants had higher CSF concentrations of kynurenine and KYNA than subjects not given these medications. A neg. association was found between a genetic variant of ACMSD and the ratio of PIC/QUIN, indicating that a polymorphism in ACMSD is associated with excess of QUIN formation at the expense of PIC. The present results confirm that the kynurenine pathway is activated in bipolar disorder, and suggest that shifting the activity of the kynurenine pathway away from QUIN production towards a production of KYNA and PIC might be a beneficial therapeutic strategy.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: (S)-2-Bromosuccinic acid( cas:20859-23-8 ) is researched.Application of 20859-23-8.Robinson, James E.; Brimble, Margaret A. published the article 《Synthesis of the anti-Helicobacter pylori agent (+)-spirolaxine methyl ether and the unnatural (2”S)-diastereomer》 about this compound( cas:20859-23-8 ) in Organic & Biomolecular Chemistry. Keywords: asym synthesis spirolaxine methyl ether Julia Kocienski olefination lactonization; spirocyclization asym synthesis methylspirolaxine mol structure absolute configuration. Let’s learn more about this compound (cas:20859-23-8).

The first enantioselective synthesis of the anti-Heliocbacter pylori agent (+)-spirolaxine Me ether (I) has been carried out in a convergent fashion establishing that the absolute stereochem. of the natural product is in fact (3R, 2”R, 5”R, 7”R) after initial synthesis of the unnatural (2”S)-diastereomer. The key step in the synthesis of (+)-spirolaxine Me ether involved a heterocycle-activated Julia-Kocienski olefination between benzothiazole-based spiroacetal sulfone II and phthalide aldehyde. (2”R, 5”S, 7”S)-spiroacetal sulfone II was prepared via cyclization of a protected dihydroxyketone, which in turn was derived from the coupling of the acetylide derived from a (R)-acetylene with phthalide aldehyde. Phthalide aldehyde was prepared via intramol. acylation of a bromocarbamate III, which was available via titanium tetrafluoride-(+)-BINOL-mediated allylation of 3,5-dimethoxybenzaldehyde. Union of the sulfone II and phthalide aldehyde fragments successfully completed the enantioselective synthesis of I. The synthesis of the unnatural (3R, 2”S, 5”R, 7”R)-diastereomer of I was also undertaken in a similar manner by union of phthalide aldehyde with (2”S, 5”S, 7”S)-spiroacetal sulfone derived from the (S)-acetylene.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 4-Hydroxyquinoline-2-carboxylic Acid, is researched, Molecular C10H7NO3, CAS is 492-27-3, about Psychological symptoms and salivary inflammatory biomarkers in patients with dentofacial deformities: a case-control study.HPLC of Formula: 492-27-3.

Individuals with dentofacial deformities often display a low quality of life (QoL) through biol. mechanisms that remain unraveled. In this case-control study, the salivary levels of cytokines, glutamate, and kynurenine metabolites were assessed in patients undergoing orthognathic surgery (OS), while correlating these parameters with QoL and psychol. symptoms. Thirty-six patients were enrolled in control (under orthodontic treatment) and test (undergoing OS) groups, matched by age and sex. The QoL was assessed through the World Health Organization Quality of Life BREF (WHOQOL-BREF) and the Orthognathic Quality of Life Questionnaire (OQLQ). The psychol. symptoms were evaluated by the Satisfaction with Life Scale, the Rosenberg Self-Esteem Scale (RSES), and the Depression, Anxiety, and Stress Scale-21 (DASS-21). The salivary levels of IL-1β, IL-6, IL-10, glutamate, and kynurenine metabolites were evaluated. The OQLQ demonstrated increased QoL scores in the test group, regarding social aspects, facial esthetics, and function domains, without significant differences in respect to the other surveys. These patients displayed higher IL-1β and glutamate levels; conversely, the kynurenine metabolites were unaltered. The glutamate levels pos. correlated with the OQLQ function scores. The data brings novel evidence about the psychobiol. features of patients with dentofacial deformities, showing salivary variations of inflammatory biomarkers in these individuals.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Stress (Abingdon, United Kingdom) called Changes in kynurenine pathway metabolites after acute psychosocial stress in healthy males: a single-arm pilot study, Author is La Torre, Danique; Dalile, Boushra; de Loor, Henriette; Van Oudenhove, Lukas; Verbeke, Kristin, which mentions a compound: 492-27-3, SMILESS is O=C(C1=NC2=CC=CC=C2C(O)=C1)O, Molecular C10H7NO3, SDS of cas: 492-27-3.

Chronic stress is associated with an increased conversion of tryptophan (TRP) into kynurenine (KYN). However, only a few studies investigated KYN pathway metabolite concentrations following acute stress in healthy subjects. We hypothesized that TRP/KYN metabolism changes following acute stress, and that KYN pathway metabolites are associated with cortisol and subjective stress responses. In a single-arm pilot study, we explored whether KYN pathway metabolites concentrations were altered after acute stress induced by the Maastricht Acute Stress Test in healthy males (n=56, mean age: 27 (SD = 4.5) years, BMI: 23 (SD = 1.8) kg/m2). In particular, we examined whether concentrations of TRP decreased, and KYN, kynurenic acid (KYNA), and the ratio of KYN to TRP (KYN:TRP) increased after acute stress. Furthermore, we assessed whether cortisol and subjective stress responses correlated with KYN pathway metabolite measures after stress induction, based on both the area under the curve with respect to the ground (AUCg) as well as the incremental area under the curve (AUCi). Concentrations of TRP, KYN, KYNA, and KYN:TRP were significantly lower after stress induction compared to pre-stress induction (all p < 0.01). AUCi and AUCg reflecting cortisol and subjective stress responses did not correlate with AUCi and AUCg reflecting KYN pathway metabolite responses. These preliminary results indicate that KYN pathway metabolites are lower after acute psychosocial stress induction. Moreover, although chronic stress and subsequent prolonged elevated cortisol concentrations and subjective stress stimulate the conversion of TRP into KYN, acute stress is not associated with such conversion up to 35 min after stress induction. From this literature《Changes in kynurenine pathway metabolites after acute psychosocial stress in healthy males: a single-arm pilot study》,we know some information about this compound(492-27-3)SDS of cas: 492-27-3, but this is not all information, there are many literatures related to this compound(492-27-3).

Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Integrated omics analysis reveals the alteration of gut microbe-metabolites in obese adults, published in 2021, which mentions a compound: 492-27-3, Name is 4-Hydroxyquinoline-2-carboxylic Acid, Molecular C10H7NO3, Recommanded Product: 4-Hydroxyquinoline-2-carboxylic Acid.

Obesity, a risk to health, is a global problem in modern society. The prevalence of obesity was approx. 13among world′s adult population. Recently, several reports suggested that the interference of gut microbiota composition and function is associated with metabolic disorders, including obesity. Gut microbiota produce a board range of metabolites involved in energy and glucose homeostasis, leading to the alteration in host metabolism However, systematic evaluation of the relationship between gut microbiota, gut metabolite and host metabolite profiles in obese adults is still lacking. In this study, we used comparative metagenomics and metabolomics anal. to determine the gut microbiota and gut-host metabolite profiles in six normal and obese adults of Chinese origin, resp. Following the functional and pathway anal., we aimed to understand the possible impact of gut microbiota on the host metabolites via the change in gut metabolites. The result showed that the change in gut microbiota may result in the modulation of gut metabolites contributing to glycolysis, tricarboxylic acid cycle and homolactic fermentation Furthermore, integrated metabolomic anal. demonstrated a possible pos. correlation of dysregulated metabolites in the gut and host, including l-phenylalanine, l-tyrosine, uric acid, kynurenic acid, cholesterol sulfate and glucosamine, which were reported to contribute to metabolic disorders such as obesity and diabetes. The findings of this study provide the possible association between gut microbiota-metabolites and host metabolism in obese adults. The identified metabolite changes could serve as biomarkers for the evaluation of obesity and metabolic disorders.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 492-27-3, is researched, Molecular C10H7NO3, about KYNA Derivatives with Modified Skeleton; Hydroxyquinolines with Potential Neuroprotective Effect †, the main research direction is review KYNA hydroxyquinoline neuroprotective agent modified skeleton; Conrad–Limpach reaction; kynurenic acid; modified Mannich reaction; modified hydroxyquinolines; neuroprotection.Synthetic Route of C10H7NO3.

A review. Kynurenic acid (KYNA) is an endogenous neuroprotective agent of increasing importance. Several derivatives have already been synthesized, bearing an abundance of functional groups attached to the main skeleton in different positions. Several of these compounds have already been tested in biol. evaluations, with several of them targeting the same receptors and biol. effects as KYNA. However, these modified compounds build upon the unmodified KYNA skeleton leaving a possible route for the synthesis of new, potentially neuroprotective derivatives with heteroatom-containing ring systems. The aim of this review is to summarize the syntheses of KYNA derivatives with altered skeletons and to pinpoint an appealing transformation for future medicinal lead mols.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

Safety of 4-Hydroxyquinoline-2-carboxylic Acid. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 4-Hydroxyquinoline-2-carboxylic Acid, is researched, Molecular C10H7NO3, CAS is 492-27-3, about Does the type of exercise affect tryptophan catabolism in horses?. Author is Kedzierski, W.; Sadok, I.; Kowalik, S.; Janczarek, I.; Staniszewska, M..

Tryptophan (Trp) is an essential amino acid which metabolises via the kynurenine pathway to generate a number of bioactive substances referred to as kynurenines. Among those are 3-hydroxykynurenine (3-HKyn) and quinolinic acid, which are neurotoxic, as well as kynurenic acid (Kyna) and xanthurenic acid (XA), which, similarly to nicotinamide (NAm), show neuroprotective and anti-depressive effects. Routine exercise is known to modulate Trp metabolism in skeletal muscle and is thus believed to reduce the risk of depressive states in humans and laboratory animals. Analogously, it was hypothesised that exercise can influence Trp metabolism in horses as well. The aim of this study was to evaluate the influence of two different types of exercise on Trp metabolism in horses of the same breed. A total of 32 purebred Arabian horses were involved in the study. The 22 three-year-old racehorses were subjected to short-time intense exercise. Ten other horses were made to perform endurance competitions at a distance of 80 km. Blood samples were collected at rest and following the end of the exercise period. Plasma concentrations of Trp, kynurenine (Kyn), Kyna, 3-HKyn, XA and NAm were determined using Ultra-High Performance Liquid Chromatog.-Electrospray Ionisation-Tandem Mass Spectrometry. Short-time intense exercise led to an increase in plasma concentrations of Kyn, Kyna and XA. The endurance effort induced an increase in Kyna and a decrease in Trp and NAm levels. Both types of exercise, short-time intensive exercise and endurance exercise induced an increase in Trp metabolites, especially Kyna, and did not induce an increase in Trp level. Thus, from a pathophysiol. perspective of the kynurenine pathway′s influence on mental state, both types of exercise induced beneficial effects in horses.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”