October 2022 - Page 19 of 72 - Indole Building Blocks

Dong, Fangcong’s team published research in Gut Microbes in 2020 | CAS: 120-72-9

1H-Indole(cas: 120-72-9) belongs to indole. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Application In Synthesis of 1H-Indole

《Intestinal microbiota-derived tryptophan metabolites are predictive of Ah receptor activity》 was written by Dong, Fangcong; Hao, Fuhua; Murray, Iain A.; Smith, Philip B.; Koo, Imhoi; Tindall, Alyssa M.; Kris-Etherton, Penny M.; Gowda, Krishne; Amin, Shantu G.; Patterson, Andrew D.; Perdew, Gary H.. Application In Synthesis of 1H-Indole And the article was included in Gut Microbes in 2020. The article conveys some information:

Commensal microbiota-dependent tryptophan catabolism within the gastrointestinal tract is known to exert profound effects upon host physiol., including the maintenance of epithelial barrier and immune function. Using GC/MS and LC/MS platforms, quantification of these novel AHR activators, along with previously established AHR-activating tryptophan metabolites, was achieved, providing a relative order of abundance. Using physiol. relevant concentrations and quant. gene expression analyses, the relative efficacy of these tryptophan metabolites with regard to mouse or human AHR activation potential is examined These data reveal indole, 2-oxindole, indole-3-acetic acid and kynurenic acid as the dominant AHR activators in mouse cecal contents and human stool from participants on a controlled diet. Here we provide the first documentation of the relative abundance and AHR activation potential of a panel of microbiota-derived tryptophan metabolites. Furthermore, these data reveal the human AHR to be more sensitive, at physiol. relevant concentrations, to tryptophan metabolite activation than mouse AHR. Addnl., correlation analyses indicate a relationship linking major tryptophan metabolite abundance with AHR activity, suggesting these cecal/fecal metabolites represent biomarkers of intestinal AHR activity.1H-Indole(cas: 120-72-9Application In Synthesis of 1H-Indole) was used in this study.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Shanina, Elena’s team published research in Glycobiology in 2021 | CAS: 399-52-0

5-Fluoro-1H-indole(cas: 399-52-0) is a member of aromaticfluorinated building blocks. Depending on which substituents are present, fluoroaromatic intermediates can be converted into fluorinated or fluorine-free commercial end products.Fluorine-containing aromatics have been incorporated into drugs (hypnotics, tranquilizers, antiinflammatory agents, analgesics, antibacterials).Application of 399-52-0

Application of 399-52-0In 2021 ,《Protein-observed 19F NMR of LecA from Pseudomonas aeruginosa》 appeared in Glycobiology. The author of the article were Shanina, Elena; Siebs, Eike; Zhang, Hengxi; Silva, Daniel Varon; Joachim, Ines; Titz, Alexander; Rademacher, Christoph. The article conveys some information:

The carbohydrate-binding protein LecA (PA-IL) from Pseudomonas aeruginosa plays an important role in the formation of biofilms in chronic infections. Development of inhibitors to disrupt LecA-mediated biofilms is desired but it is limited to carbohydrate-based ligands. Moreover, discovery of drug-like ligands for LecA is challenging because of its weak affinities. Therefore, we established a protein-observed 19F (PrOF) NMR (NMR) to probe ligand binding to LecA. LecA was labeled with 5-fluoroindole to incorporate 5-fluorotryptophanes and the resonances were assigned by site-directed mutagenesis. This incorporation did not disrupt LecA preference for natural ligands, Ca2+ and D-galactose (D-Gal). Following NMR perturbation of W42, which is located in the carbohydrate-binding region of LecA, allowed to monitor binding of low-affinity ligands such as N-acetyl D-galactosamine (D-GalNAc, Kd = 780 ± 97 μM). Moreover, PrOF NMR titration with glycomimetic of LecA p-nitrophenyl β-D-galactoside (pNPGal, Kd = 54 ± 6 μM) demonstrated a 6-fold improved binding of D-Gal proving this approach to be valuable for ligand design in future drug discovery campaigns that aim to generate inhibitors of LecA.5-Fluoro-1H-indole(cas: 399-52-0Application of 399-52-0) was used in this study.

Xie, Guilin’s team published research in Organic Letters in 2021 | CAS: 399-52-0

Application In Synthesis of 5-Fluoro-1H-indoleIn 2021 ,《Palladium-Catalyzed Direct and Specific C-7 Acylation of Indolines with 1,2-Diketones》 appeared in Organic Letters. The author of the article were Xie, Guilin; Zhao, Yuhan; Cai, Changqun; Deng, Guo-Jun; Gong, Hang. The article conveys some information:

Herein, a palladium-catalyzed direct and specific C-7 acylation of indolines in the presence of an easily removed directing group was developed. This strategy usually considered as a practical strategy for the preparation of acylated indoles because indoline can be easily converted to indole under oxidation conditions. In particular, these strategy greatly improved the alkacylation yield of indolines for which only an unsatisfactory yield could be achieved in the previous studies. Furthermore, the reaction can be scaled up to gram level in the standard reaction conditions with a much lower palladium loading (1 mol %). The experimental process involved the reaction of 5-Fluoro-1H-indole(cas: 399-52-0Application In Synthesis of 5-Fluoro-1H-indole)

Dong, Fangcong’s team published research in Gut Microbes in 2020 | CAS: 120-72-9

Reference of 1H-IndoleIn 2020 ,《The aryl hydrocarbon receptor as a mediator of host-microbiota interplay》 appeared in Gut Microbes. The author of the article were Dong, Fangcong; Perdew, Gary H.. The article conveys some information:

A review. Increasing evidence suggests a significant role for microbiota dependent metabolites and co-metabolites, acting as aryl hydrocarbon receptor (AHR) ligands, to facilitate bidirectional communication between the host and the microbiota and thus modulate physiol. Such communication is particularly evident within the gastrointestinal tract. Through binding to or activating the AHR, these metabolites play fundamental roles in various physiol. processes and likely contribute to the maintenance of intestinal homeostasis. In recent years, tryptophan metabolites were screened to identify physiol. relevant AHR ligands or activators. The discovery of specific microbiota-derived indole-based metabolites as AHR ligands may provide insight concerning how these metabolites affect interactions between gut microbiota and host intestinal homeostasis and how this relates to chronic GI disease and overall health. A greater understanding of the mechanisms that modulate the production of such metabolites and associated AHR activity may be utilized to effectively treat inflammatory diseases and promote human health. Here, we review microbiota-derived AHR ligands generated from tryptophan that modulate host-gut microbiota interactions and discuss possible intervention strategies for potential therapies in the future. In the part of experimental materials, we found many familiar compounds, such as 1H-Indole(cas: 120-72-9Reference of 1H-Indole)

Feng, Zhihui’s team published research in Food Chemistry in 2019 | CAS: 120-72-9

Safety of 1H-IndoleIn 2019 ,《Tea aroma formation from six model manufacturing processes》 was published in Food Chemistry. The article was written by Feng, Zhihui; Li, Yifan; Li, Ming; Wang, Yijun; Zhang, Liang; Wan, Xiaochun; Yang, Xiaogen. The article contains the following contents:

Tea aroma is determined by the nature of the plant, the production processes, and many other factors influencing its formation and release. The objective of this study was to investigate the impact of manufacturing processes on the aroma composition of tea. Fresh tea leaves from the same cultivar and growing area were selected for producing the six types of tea: green, white, yellow, oolong, black, and dark teas. Comprehensive anal. by gas chromatog. mass spectrometry (GC/MS) was performed for the volatiles of tea infusion, prepared by solid-phase microextraction (SPME), solid-phase extraction (SPE), and solvent assisted flavor evaporation (SAFE). A total of 168 volatile compounds were identified. Black tea has the highest volatile concentration of 710 μg/g, while green tea has the lowest concentration of 20 μg/g. Significantly affected by these processes, tea aroma mols. are formed mainly from four precursor groups: carotenoids, fatty acids, glycosides, and amino acids/sugars. In the experiment, the researchers used 1H-Indole(cas: 120-72-9Safety of 1H-Indole)

Zhang, Lin-Bao’s team published research in ACS Catalysis in 2019 | CAS: 399-52-0

5-Fluoro-1H-indole(cas: 399-52-0) is a member of aromaticfluorinated building blocks. Fluorine-containing aromatics have been incorporated into crop-protection chemicals (herbicides, insecticides, fungicides). Liquid crystals, positron emission tomography, and imaging systems represent new areas where fluoroaromatics and fluoroheterocyclics have gained attention.Product Details of 399-52-0

In 2019,ACS Catalysis included an article by Zhang, Lin-Bao; Zhu, Ming-Hui; Ni, Shao-Fei; Wen, Li-Rong; Li, Ming. Product Details of 399-52-0. The article was titled 《Silver-Mediated Indole (4 + 2) Dearomative Annulation with N-Radicals: A Strategy To Construct Heterocycle-Fused Indolines》. The information in the text is summarized as follows:

A regioselective AgI-mediated dearomative (4 + 2) annulation reaction of substituted indoles has been developed. The transformation provides rapid access to functionalized heterocycle fused indoline skeletons, e.g., I, with broad functional groups, high atom economy, and an easy-to-handle nature in one step. Moreover, the recovery experiment of silver catalysts could reduce the cost. D. functional theory studies support a “”radical cation”” pathway in which C-N bond formation determines the rate-limiting step. The results came from multiple reactions, including the reaction of 5-Fluoro-1H-indole(cas: 399-52-0Product Details of 399-52-0)

Chen, Xiaohua’s team published research in Food Chemistry in 2019 | CAS: 120-72-9

In 2019,Food Chemistry included an article by Chen, Xiaohua; Chen, Dejing; Jiang, Hai; Sun, Haiyan; Zhang, Chen; Zhao, Hua; Li, Xinsheng; Yan, Fei; Chen, Chen; Xu, Zhimin. Electric Literature of C8H7N. The article was titled 《Aroma characterization of Hanzhong black tea (Camellia sinensis) using solid phase extraction coupled with gas chromatography-mass spectrometry and olfactometry and sensory analysis》. The information in the text is summarized as follows:

The unique aroma of the Hanzhong black tea is due to the special location of the harvesting place and specific manufacturing processes. In this study, a solid phase extraction method (SPE) as sample preparation tool was combined with gas chromatog. (GC) as separation technique and several detection systems such as mass spectrometry (MS), flame ionization (FID) and olfactometry (O), which, together with sensorial anal. were used to characterize aroma compounds in Hanzhong black tea infusion. Seventy three aroma compounds were identified and quantified in the tea infusion by the GC-MS and GC-FID methods, resp. Among them, odor perceptions of 24 compounds were characterized by the GC-O anal. It was found that linalool oxide I, II and III, E,E-2,4-nonadienal, 4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one, 1-octen-3-one, E,Z-2,6-nonadienal, bis(2-methyl-3-furyl) disulfide had higher odor activity value in the tea infusion and offered floral, fatty, and caramel, mushroom, cucumber, and cooked beef -like odors, resp. Overall, floral and mushroom and caramel -like odors significantly dominated in the Hanzhong black tea infusion.1H-Indole(cas: 120-72-9Electric Literature of C8H7N) was used in this study.

Wu, Zhiqiang’s team published research in Green Chemistry in 2019 | CAS: 120-72-9

In 2019,Green Chemistry included an article by Wu, Zhiqiang; Wang, Gang; Yuan, Shuo; Wu, Dan; Liu, Wanyi; Ma, Baojun; Bi, Shuxian; Zhan, Haijuan; Chen, Xiaoyan. SDS of cas: 120-72-9. The article was titled 《Synthesis of bis(indolyl)methanes under dry grinding conditions, promoted by a Lewis acid-surfactant-SiO2-combined nanocatalyst》. The information in the text is summarized as follows:

An in situ developed Lewis acid-surfactant-SiO2-combined (LASSC) nanocatalyst was used, for the first time, as a green and effective promoting medium for the electrophilic activation of aldehydes RCHO (R = 4-nitrophenyl, 2,4-dichlorophenyl, 3,4-dihydroxyphenyl, etc.) under solvent-free and dry grinding conditions. The advantages of using the LASSC nanocatalyst include avoiding the generation of wastewater containing sodium dodecyl sulfate and the use of toxic reagents, excellent reusability of the catalyst, and obtaining a high yield of bis(indolyl)methanes I (R1 = 6-NO2, 2-Me, 3-Me, etc.). In the experimental materials used by the author, we found 1H-Indole(cas: 120-72-9SDS of cas: 120-72-9)

Li, Ling-Jun’s team published research in Organic Letters in 2020 | CAS: 399-52-0

《Synthesis of Axially Chiral Olefin-Oxazoline Ligands via Pd-Catalyzed Multiple C-H Functionalization》 was published in Organic Letters in 2020. These research results belong to Li, Ling-Jun; Chen, Jun-Jie; Feng, Chen-Fei; Li, Han-Yuan; Wang, Xing; Xu, Hui; Dai, Hui-Xiong. Quality Control of 5-Fluoro-1H-indole The article mentions the following:

We report herein the Pd-catalyzed oxazoline-directed C-H olefination of the N-arylindole skeleton, affording two diastereomers of axially chiral olefin-oxazoline ligands in a one-step procedure. Modifications at the 3- and 3′-positions were facilely achieved via electrophilic substitution of the indole fragment and subsequent oxazoline-directed C-H amidation or olefination of the arene fragment.5-Fluoro-1H-indole(cas: 399-52-0Quality Control of 5-Fluoro-1H-indole) was used in this study.

Ruiz-Ruiz, Susana’s team published research in Aging Cell in 2020 | CAS: 120-72-9

《Functional microbiome deficits associated with ageing: Chronological age threshold》 was written by Ruiz-Ruiz, Susana; Sanchez-Carrillo, Sergio; Ciordia, Sergio; Mena, Maria C.; Mendez-Garcia, Celia; Rojo, David; Bargiela, Rafael; Zubeldia-Varela, Elisa; Martinez-Martinez, Monica; Barbas, Coral; Ferrer, Manuel; Moya, Andres. Related Products of 120-72-9 And the article was included in Aging Cell in 2020. The article conveys some information:

Composition of the gut microbiota changes during aging, but questions remain about whether age is also associated with deficits in microbiome function and whether these changes occur sharply or progressively. The ability to define these deficits in populations of different ages may help determine a chronol. age threshold at which deficits occur and subsequently identify innovative dietary strategies for active and healthy aging. Here, active gut microbiota and associated metabolic functions were evaluated using shotgun proteomics in three well-defined age groups consisting of 30 healthy volunteers, namely, ten infants, ten adults and ten elderly individuals. Samples from each volunteer at intervals of up to 6 mo (n = 83 samples) were used for validation. Aging gradually increases the diversity of gut bacteria that actively synthesize proteins, that is by 1.4-fold from infants to elderly individuals. An anal. of functional deficits consistently identifies a relationship between tryptophan and indole metabolism and aging (p < 2.8e-8). Indeed, the synthesis of proteins involved in tryptophan and indole production and the fecal concentrations of these metabolites are directly correlated (r2 > .987) and progressively decrease with age (r2 > .948). An age threshold for a 50% decrease is observed ca. 11-31 years old, and a greater than 90% reduction is observed from the ages of 34-54 years. Based on recent investigations linking tryptophan with abundance of indole and other “”healthy”” longevity mols. and on the results from this small cohort study, dietary interventions aimed at manipulating tryptophan deficits since a relatively “”young”” age of 34 and, particularly, in the elderly are recommended. The experimental part of the paper was very detailed, including the reaction process of 1H-Indole(cas: 120-72-9Related Products of 120-72-9)