19/10/2022 - Indole Building Blocks

Ellervik, Ulf’s team published research in Carbohydrate Research in 1996 | CAS: 99409-32-2

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2) belongs to indole.The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.Safety of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranosideThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.

Ellervik, Ulf; Magnusson, Goeran published an article on January 11 ,1996. The article was titled 《Glycosylation with N-Troc-protected glycosyl donors》, and you may find the article in Carbohydrate Research.Safety of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside The information in the text is summarized as follows:

N-troc-protected (Troc = 2,2,2-trichloroethoxycarbonyl) glucosamine and galactosamine glycosyl donors, e.g. I (R1,R2 = H, OAc), (1-O-acetyl sugar, bromo sugar, and thioglycoside) were compared with the corresponding N-Phth-protected derivatives II (R1,R2 = H, OAc)in glycosylations of 2-(trimethylsilyl)ethanol, 2-bromoethanol, Me 3-mercaptopropionate, N-Fmoc-protected serine, and 2-(trimethylsilyl)ethyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside. The N-Troc-protected donors gave pure β-glycosides in somewhat higher yields than the N-Phth-protected counterparts. The N-Troc protecting group can be removed by reduction with zinc, which allows selective N-deprotection in oligosaccharides containing both N-Troc and N-Phth groups. The results came from multiple reactions, including the reaction of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2Safety of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside)

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

Veeneman, G. H.’s team published research in Tetrahedron Letters in 1990 | CAS: 99409-32-2

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2) belongs to indole.The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.Category: indole-building-blockThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.

The author of 《Iodonium ion-promoted reactions at the anomeric center. II. An efficient thioglycoside-mediated approach toward the formation of 1,2-trans-linked glycosides and glycosidic esters》 were Veeneman, G. H.; Van Leeuwen, S. H.; Van Boom, J. H.. And the article was published in Tetrahedron Letters in 1990. Category: indole-building-block The author mentioned the following in the article:

N-Iodosuccinimide (I) in the presence of an organic acid was effective for the activation of fully acylated thioglycosides leading to 1,2-trans linked esters. For example, tetrabenzoylthiogalactopyranoside II (R = EtS) was treated with I and MeOCH2CO2H in Et2O-ClCH2CH2Cl to give 98% II (R = MeOCH2CO2). On the other hand, I together with a catalytic amount of trifluoromethanesulfonic acid was very convenient for the rapid, high-yielding and stereoselective (1,2-trans) glycosidation of esterified thioglycosides with glycosyl acceptors, e.g., III, to give title compds, e.g., IV.Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2Category: indole-building-block) was used in this study.

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2) belongs to indole.The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.Category: indole-building-blockThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.

Nguyen, Ngoc-Khanh’s team published research in Molecular Catalysis in 2021 | 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.Computed Properties of C8H6FN

Nguyen, Ngoc-Khanh; Nam, Duong Ha; Phuc, Ban Van; Nguyen, Van Ha; Trinh, Quang Thang; Hung, Tran Quang; Dang, Tuan Thanh published their research in Molecular Catalysis in 2021. The article was titled 《Efficient copper-catalyzed synthesis of C3-alkylated indoles from indoles and alcohols》.Computed Properties of C8H6FN The article contains the following contents:

A highly efficient copper(II) catalyst system for alkylation of indoles with alcs. via hydrogen borrowing method has been developed to afford C3-alkylated indoles I (R1 = H, 5-OMe, 7-Me, etc.; R2 = n-pentyl, Ph, 3-FC6H4, etc.) in good to excellent yields. Cu(OAc)2 in the combination with dppm ligand has been found to be the most suitable catalyst system for this alkylation reaction. After reading the article, we found that the author used 5-Fluoro-1H-indole(cas: 399-52-0Computed Properties of C8H6FN)

Agostini, Federica’s team published research in ACS Central Science in 2021 | CAS: 399-52-0

Agostini, Federica; Sinn, Ludwig; Petras, Daniel; Schipp, Christian J.; Kubyshkin, Vladimir; Berger, Allison Ann; Dorrestein, Pieter C.; Rappsilber, Juri; Budisa, Nediljko; Koksch, Beate published an article in 2021. The article was titled 《Multiomics Analysis Provides Insight into the Laboratory Evolution of Escherichia coli toward the Metabolic Usage of Fluorinated Indoles》, and you may find the article in ACS Central Science.Formula: C8H6FN The information in the text is summarized as follows:

Organofluorine compounds are known to be toxic to a broad variety of living beings in different habitats, and chem. fluorination has been historically exploited by mankind for the development of therapeutic drugs or agricultural pesticides. However, several studies so far demonstrated that, under appropriate conditions, living systems (in particular bacteria) can tolerate the presence of fluorinated mols. (e.g., amino acids analogs) within their metabolism and even repurpose them as alternative building blocks for the synthesis of cellular macromols. such as proteins. Understanding the mol. mechanism behind these phenomena would greatly advance approaches to the biotechnol. synthesis of recombinant proteins and peptide drugs. However, information about the metabolic effects of long-term exposure of living cells to fluorinated amino acids remains scarce. Hereby, the authors report the long-term propagation of Escherichia coli (E. coli) in an artificially fluorinated habitat that yielded two strains naturally adapted to live on fluorinated amino acids. In particular, the authors applied selective pressure to force a tryptophan (Trp)-auxotrophic strain to use either 4- or 5-fluoroindole as essential precursors for the in situ synthesis of Trp analogs, followed by their incorporation in the cellular proteome. Full adaptation to both fluorinated Trp analogs requires a low number of genetic mutations but is accompanied by large rearrangements in regulatory networks, membrane integrity, and quality control of protein folding. These findings highlight the cellular mechanisms behind the adaptation to unnatural amino acids and provide the mol. foundation for bioengineering of novel microbial strains for synthetic biol. and biotechnol. The authors eliminated the metabolic ability of E. coli to produce the canonical amino acid tryptophan and introduced synthesis of two fluorinated analogs in vivo using 4- and 5-fluoroindole as precursors. After reading the article, we found that the author used 5-Fluoro-1H-indole(cas: 399-52-0Formula: C8H6FN)

Qin, Hong’s team published research in Journal of Organic Chemistry 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).Related Products of 399-52-0

Qin, Hong; Zhang, Jie; Qiao, Kai; Zhang, Dong; He, Wei; Liu, Chengkou; Fang, Zheng; Guo, Kai published an article in 2021. The article was titled 《Palladium-Catalyzed C2-Regioselective Perfluoroalkylation of the Free (NH)-Heteroarenes》, and you may find the article in Journal of Organic Chemistry.Related Products of 399-52-0 The information in the text is summarized as follows:

A highly regioselective and atom-efficient strategy for the construction of fused free (NH) heteroarenes I (R = 3-Me, 4-Cl, 7-F, etc.) and II (R1 = 2-C(O)2Me, 3-C(O)2Me, 3-C(O)2Et-4-Me) through a palladium-catalyzed perfluoroalkyl insertion reaction has been accomplished. This protocol employed multiple iodofluoroalkanes R2I [R2 = 1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexyl, 1,1,2,2,3,3,3-heptafluoropropyl, (benzenesulfonyl)difluoromethyl, etc.] as practical and available perfluoroalkyl sources to provide an operationally simple and versatile route for the synthesis of perfluoroalkylated indoles III. Moreover, indoles I without the assistance of guide groups were utilized as substrates, achieving C(sp2)-H site-selective functionalization of indoles I in yields up to 95%. Furthermore, this protocol was also used for late-stage C2 perfluoroalkylation of bioactive compounds such as auxin, tryptophan, and melatonin analogs. The experimental part of the paper was very detailed, including the reaction process of 5-Fluoro-1H-indole(cas: 399-52-0Related Products of 399-52-0)

Nasr, Mohamed A.’s team published research in ACS Synthetic Biology in 2022 | 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.Recommanded Product: 1H-Indole

In 2022,Nasr, Mohamed A.; Timmins, Logan R.; Martin, Vincent J. J.; Kwan, David H. published an article in ACS Synthetic Biology. The title of the article was 《A Versatile Transcription Factor Biosensor System Responsive to Multiple Aromatic and Indole Inducers》.Recommanded Product: 1H-Indole The author mentioned the following in the article:

Allosteric transcription factor (aTF) biosensors are valuable tools for engineering microbes toward a multitude of applications in metabolic engineering, biotechnol., and synthetic biol. One of the challenges toward constructing functional and diverse biosensors in engineered microbes is the limited toolbox of identified and characterized aTFs. To overcome this, extensive bioprospecting of aTFs from sequencing databases, as well as aTF ligand-specificity engineering are essential in order to realize their full potential as biosensors for novel applications. In this work, using the TetR-family repressor CmeR from Campylobacter jejuni, we construct aTF genetic circuits that function as salicylate biosensors in the model organisms Escherichia coli and Saccharomyces cerevisiae. In addition to salicylate, we demonstrate the responsiveness of CmeR-regulated promoters to multiple aromatic and indole inducers. This relaxed ligand specificity of CmeR makes it a useful tool for detecting mols. in many metabolic engineering applications, as well as a good target for directed evolution to engineer proteins that are able to detect new and diverse chemistries. The results came from multiple reactions, including the reaction of 1H-Indole(cas: 120-72-9Recommanded Product: 1H-Indole)

Li, Xiaojing’s team published research in Frontiers in Pharmacology in 2021 | CAS: 120-72-9

Safety of 1H-IndoleIn 2021 ,《New insights into gut-bacteria-derived indole and its derivatives in intestinal and liver diseases》 appeared in Frontiers in Pharmacology. The author of the article were Li, Xiaojing; Zhang, Binbin; Hu, Yiyang; Zhao, Yu. The article conveys some information:

A review. The interaction between host and microorganism widely affects the immune and metabolic status. Indole and its derivatives are metabolites produced by the metabolism of tryptophan catalyzed by intestinal microorganisms. By activating nuclear receptors, regulating intestinal hormones, and affecting the biol. effects of bacteria as signaling mols., indole and its derivatives maintain intestinal homeostasis and impact liver metabolism and the immune response, which shows good therapeutic prospects. We reviewed recent studies on indole and its derivatives, including related metabolism, the influence of diets and intestinal commensal bacteria, and the targets and mechanisms in pathol. conditions, especially progress in therapeutic strategies. New research insights into indoles will facilitate a better understanding of their dimmunity ruggability and application in intestinal and liver diseases. After reading the article, we found that the author used 1H-Indole(cas: 120-72-9Safety of 1H-Indole)

Herraiz, Tomas’s team published research in Free Radical Research in 2002 | CAS: 59132-30-8

2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole-1,3-dicarboxylic acid(cas: 59132-30-8) belongs to indole.The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.Safety of 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole-1,3-dicarboxylic acidThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.

《Tetrahydro-β-carboline alkaloids that occur in foods and biological systems act as radical scavengers and antioxidants in the ABTS assay》 was written by Herraiz, Tomas; Galisteo, Juan. Safety of 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole-1,3-dicarboxylic acid And the article was included in Free Radical Research on August 31 ,2002. The article conveys some information:

Tetrahydro-β-carboline alkaloids that occur in foods such as wine, seasonings, vinegar and fruit products (juices, jams) acted as good radical scavengers (hydrogen- or electron donating) in the ABTS (2,2′-Azinobis-(3-ethylbenzothiazoline-6-sulfonic acid)) assay, and therefore, they could contribute to the beneficial antioxidant capacity attributed to foods. In contrast, the fully aromatic β-carbolines norharman and harman did not show any radical scavenger activity in the same assay. During the reaction with ABTS + radical cation, tetrahydro-β-carboline-3-carboxylic acid such as 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (MTCA) and 1-methyl-1,2,3,4-tetrahydro-β-carboline-1,3-dicarboxylic acid (MTCA-COOH) were converted to harman, whereas 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (THCA) and 1,2,3,4-tetrahydro-β-carboline-1,3-dicarboxylic acid (THCA-COOH) afforded norharman. These results suggest that food and naturally-occurring tetrahydro-β-carboline alkaloids if accumulated in tissues, as reported elsewhere, might exhibit antioxidant activity. In the experimental materials used by the author, we found 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole-1,3-dicarboxylic acid(cas: 59132-30-8Safety of 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole-1,3-dicarboxylic acid)

Garegg, Per J.’s team published research in Carbohydrate Research in 1992 | CAS: 99409-32-2

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2) belongs to indole.The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.Category: indole-building-blockThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.

Garegg, Per J.; Oscarson, Stefan; Tiden, Anna Karin published an article on February 17 ,1992. The article was titled 《Synthesis of p-trifluoroacetamidophenyl 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-mannopyranosiduronic acid, an artificial antigen corresponding to a disaccharide repeating unit of the capsular polysaccharide of Haemophilus influenzae type e》, and you may find the article in Carbohydrate Research.Category: indole-building-block The information in the text is summarized as follows:

The title compound I was prepared from 4-nitrophenyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-mannopyranoside via glycosidation of silylated azidodeoxymannopyranoside II with Et 2,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (III). After reading the article, we found that the author used Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2Category: indole-building-block)

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2) belongs to indole.The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.Category: indole-building-blockThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.

Ma, Qiao’s team published research in Journal of Hazardous Materials in 2019 | CAS: 120-72-9

In 2019,Journal of Hazardous Materials included an article by Ma, Qiao; Liu, Ziyan; Yang, Bingyu; Dai, Chunxiao; Qu, Yuanyuan. Application of 120-72-9. The article was titled 《Characterization and functional gene analysis of a newly isolated indole-degrading bacterium Burkholderia sp. IDO3》. The information in the text is summarized as follows:

Indole is a common N-heterocyclic pollutant as well as a signaling mol. widespread in various environmental matrixes. Several bacterial strains have been reported to be able to degrade indole, while the degradation capacity and functional enzymes are poorly documented. Herein, the degradation characteristics of a newly-isolated indole-degrading strain Burkholderia sp. IDO3 were carefully investigated. Strain IDO3 exhibited superior degradation ability which could completely remove 100 mg/L indole within 14 h in mineral salt medium. It maintained comparable degradation performance under conditions of pH 4.0-9.0, temperature 25-35 °C and rotary speed 0-250 r/min, and most of the tested heavy metals and organic pollutants did not significantly affect the degradation process. Two important intermediates, i.e. isatin and anthranilate, were identified in indole degradation process. The genomic clone library technique with indigo-based screening method was successfully applied to screen the functional genes. Heterologous expression assay proved that recombinant E. coli strain carrying indole oxygenase and reductase genes iifCD could transform indole to indigo. Bioinformatic analyses indicated that the newly obtained enzyme IifC_IDO3 formed a phylogenetically sep. branch from other related aromatic oxygenases. This study provides new insights into our understanding of indole degradation by Burkholderia strains and offers efficient bacterial resource for indole bioremediation. The results came from multiple reactions, including the reaction of 1H-Indole(cas: 120-72-9Application of 120-72-9)