Indole Building Blocks

Sekhar, Abinitha S.’s team published research in International Journal of Pharmaceutical Sciences Review and Research in 2016 | CAS: 162100-42-7

6-Chloro-5-methyl-1H-indole(cas: 162100-42-7) is a member of organic chlorides. Organic chlorides are compounds containing a carbon-chlorine bond, which are widely used in the oil field as a wax dissolver. They are generally not present in crude oils and are typically the result of additives, cleaning solutions or chemicals used for oil recovery.Application of 162100-42-7

In 2016,International Journal of Pharmaceutical Sciences Review and Research included an article by Sekhar, Abinitha S.; Saranya, T. S.; Baskar, Vaishnav; Manakadan, Asha Ashokan. Application of 162100-42-7. The article was titled 《In silico approach of apoptosis induing ability of different indole derivatives by interaction with caspase9》. The information in the text is summarized as follows:

Indole compounds are well known for their wide variety of pharmacol. activities. It is the combination of benzene with pyrrole ring. Compounds having indole group are biol. important. They are used as antimicrobial, antiviral, antitubercular, antiinflammatory, anticancer, ant-diabetic and anticonvulsant agents. Because of the wide variety of biol. application, several substituted indole derivatives are studied for their mol. structure, mol. docking and bioavailability. The purpose of the study is to carry out the docking studies of indole derivatives containing electrophilic substitution and nucleophilic substitution with the anticancer target casp9. Fifty compounds were designed and by using Argus lab version 4.0.1. Their docking score was calculated and compared with the standard drug casodex. The drug likeness of compounds was performed using Lipinski rule of five. Result showed that 1,1′-(1H-indole-5,6-diyl)diethanone and 5-(trichloromethyl)-1H-indole and the phytoconstituent curcumin showed better docking score than that of the standard drug casodex. It is concluded that certain indole derivatives show greater affinity with casp9 protein. These compounds may be helpful in studying anticancer targets for casp9 protein. In the part of experimental materials, we found many familiar compounds, such as 6-Chloro-5-methyl-1H-indole(cas: 162100-42-7Application of 162100-42-7)

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

Yang, Jingyun’s team published research in Proceedings of the National Academy of Sciences of the United States of America 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 of 120-72-9

《Biphasic chemotaxis of Escherichia coli to the microbiota metabolite indole》 was written by Yang, Jingyun; Chawla, Ravi; Rhee, Kathy Y.; Gupta, Rachit; Manson, Michael D.; Jayaraman, Arul; Lele, Pushkar P.. Application of 120-72-9 And the article was included in Proceedings of the National Academy of Sciences of the United States of America in 2020. The article conveys some information:

Bacterial chemotaxis to prominent microbiota metabolites such as indole is important in the formation of microbial communities in the gastrointestinal (GI) tract. However, the basis of chemotaxis to indole is poorly understood. Here, we exposed Escherichia coli to a range of indole concentrations and measured the dynamic responses of individual flagellar motors to determine the chemotaxis response. Below 1 mM indole, a repellent-only response was observed At 1 mM indole and higher, a time-dependent inversion from a repellent to an attractant response was observed The repellent and attractant responses were mediated by the Tsr and Tar chemoreceptors, resp. Also, the flagellar motor itself mediated a repellent response independent of the receptors. Chemotaxis assays revealed that receptor-mediated adaptation to indole caused a bipartite response-wild-type cells were attracted to regions of high indole concentration if they had previously adapted to indole but were otherwise repelled. We propose that indole spatially segregates cells based on their state of adaptation to repel invaders while recruiting beneficial resident bacteria to growing microbial communities within the GI tract. The results came from multiple reactions, including the reaction of 1H-Indole(cas: 120-72-9Application of 120-72-9)

Scott, Samantha A.’s team published research in Proceedings of the National Academy of Sciences of the United States of America in 2020 | CAS: 120-72-9

《Microbial tryptophan metabolites regulate gut barrier function via the aryl hydrocarbon receptor》 was written by Scott, Samantha A.; Fu, Jingjing; Chang, Pamela V.. Formula: C8H7NThis research focused ontryptophan metabolite gut barrier aryl hydrocarbon receptor disease human; Crohn disease ulcerative colitis inflammatory bowel disease cytokine; colitis; gut microbiome; inflammatory bowel disease; intestinal epithelium. The article conveys some information:

Inflammatory bowel diseases (IBDs), including Crohn’s disease and ulcerative colitis, are associated with dysbiosis of the gut microbiome. Emerging evidence suggests that small-mol. metabolites derived from bacterial breakdown of a variety of dietary nutrients confer a wide array of host benefits, including amelioration of inflammation in IBDs. Yet, in many cases, the mol. pathways targeted by these mols. remain unknown. Here, we describe roles for three metabolites-indole-3-ethanol, indole-3-pyruvate, and indole-3-aldehyde-which are derived from gut bacterial metabolism of the essential amino acid tryptophan, in regulating intestinal barrier function. We determined that these metabolites protect against increased gut permeability associated with a mouse model of colitis by maintaining the integrity of the apical junctional complex and its associated actin regulatory proteins, including myosin IIA and ezrin, and that these effects are dependent on the aryl hydrocarbon receptor. Our studies provide a deeper understanding of how gut microbial metabolites affect host defense mechanisms and identify candidate pathways for prophylactic and therapeutic treatments for IBDs. In the experiment, the researchers used many compounds, for example, 1H-Indole(cas: 120-72-9Formula: C8H7N)

Wang, Qing-Dong’s team published research in Tetrahedron Letters in 2017-07-26 | 4771-48-6

Tetrahedron Letters published new progress about Chemoselectivity. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Name: 4-Methyl-1H-indole-3-carbaldehyde.

Wang, Qing-Dong; Yang, Jin-Ming; Fang, Dong; Ren, Jiangmeng; Zeng, Bu-Bing published the artcile< Iodine-catalyzed C3-formylation of indoles using hexamethylenetetramine and air>, Name: 4-Methyl-1H-indole-3-carbaldehyde, the main research area is formylindole preparation chemoselective green chem; indole hexamethylenetetramine formylation reaction iodine catalyst.

An efficient iodine-catalyzed chemoselective 3-formylation of free (N-H) and N-substituted indoles I [R = H, 4-Me, 7-Br, etc.; R1 = H; R2 = Me, Bn, (CH2)4OH, etc.] was achieved by using hexamethylenetetramine (HMTA) in the presence of activated carbon under air atm. This new method could provide 3-formylindoles I (R1 = CHO) in moderate to excellent yields with fairly short reaction times. Moreover, this catalytic formylation of indoles procedure can be applied to gram-scale synthesis.

Tetrahedron Letters published new progress about Chemoselectivity. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Name: 4-Methyl-1H-indole-3-carbaldehyde.

Chen, Xiaoxue’s team published research in Bioorganic & Medicinal Chemistry in 2020-03-15 | 399-76-8

Bioorganic & Medicinal Chemistry published new progress about Covalent bond (SIRT2 covalent inhibitors). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Recommanded Product: 5-Fluoroindole-2-carboxylic acid.

Chen, Xiaoxue; Zou, Yefang; Wang, Jie; Cao, Zhuoxian; Liu, Jingzi; Li, Yan; Zhao, Yonglong; He, Bin published the artcile< Unexpected small molecules as novel SIRT2 suicide inhibitors>, Recommanded Product: 5-Fluoroindole-2-carboxylic acid, the main research area is sirtuin SIRT2 covalent inhibitors suicide inhibitors deacetylation deacylation; Covalent inhibitors; Deacetylation; Deacylation; SIRT2; Sirtuin; Suicide inhibitors.

A series of sirtuin inhibitor candidates were assembled based on an intermediate ester (1a) our accidently discovered. After screening and evaluation, several SIRT2 selective inhibitors were identified, which can inhibit all the deacetylation, defatty-acylation and debenzoylation of SIRT2. Among these inhibitors, compound 1e was the best SIRT2 selective inhibitors. The primary study on the inhibitory mechanism indicated that compound 1e may be a suicide inhibitor acting as an irreversible way. Given almost all reported sirtuin inhibitors are non-covalent, sirtuin covalent inhibitors are still need to be developed. These findings will facilitate for further development of SIRT2 selective and suicide inhibitors.

Tan, Yu Jia’s team published research in ACS Medicinal Chemistry Letters in 2021-05-13 | 399-76-8

ACS Medicinal Chemistry Letters published new progress about Amides, oxo Role: PAC (Pharmacological Activity), PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), THU (Therapeutic Use), BIOL (Biological Study), RACT (Reactant or Reagent), PREP (Preparation), USES (Uses). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Quality Control of 399-76-8.

Tan, Yu Jia; Li, Ming; Gunawan, Gregory Adrian; Nyantakyi, Samuel Agyei; Dick, Thomas; Go, Mei-Lin; Lam, Yulin published the artcile< Amide-Amine Replacement in Indole-2-carboxamides Yields Potent Mycobactericidal Agents with Improved Water Solubility>, Quality Control of 399-76-8, the main research area is methylamine carboxamide benzothiophene benzoselenophene preparation antimycobacterial lipophilicity.

Indolecarboxamides are potent but poorly soluble mycobactericidal agents. Here, it was found that modifying the incipient scaffold by amide-amine substitution and replacing the indole ring with benzothiophene or benzoselenophene led to striking (10-20-fold) improvements in solubility Potent activity could be achieved without the carboxamide linker but not in the absence of the indole ring. The indolylmethylamine, N-cyclooctyl-6-trifluoromethylindol-2-ylmethylamine (MIC90Mtb 0.13μM, MBC99.9Mtb 0.63μM), exemplifies a promising member that is more soluble and equipotent to its carboxamide equivalent It is also an inhibitor of the mycolate transporter MmpL3, a property shared by the methylamines of benzothiophene and benzoselenophene.

Wang, Dong’s team published research in Organic Letters in 2019-06-21 | 93247-78-0

Organic Letters published new progress about Crystal structure. 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Product Details of C10H9NO2.

Wang, Dong; Wang, Zhentao; Liu, Zhenlin; Huang, Mindong; Hu, Jianyong; Yu, Peng published the artcile< Strategic C-C Bond-Forming Dearomatization of Pyridines and Quinolines>, Product Details of C10H9NO2, the main research area is regioselective diastereoselective tetrahydropyridine tetrahydroquinoline preparation one pot aromatization; dearomative double nucleophilic addition pyridine quinoline.

A one-pot protocol for the dearomative double nucleophilic addition to pyridines and quinolines, providing convenient, regioselective and diastereoselective access to tetrahydropyridines and tetrahydroquinolines under reductant-free conditions is described. This method also offers a new strategy for the general dearomatization of nitrogen heteroaromatics

Organic Letters published new progress about Crystal structure. 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Product Details of C10H9NO2.

Peng, Xinwen’s team published research in Carbohydrate Polymers in 2019-07-15 | 950846-89-6

Carbohydrate Polymers published new progress about Antitumor agents. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Product Details of C30H36N4O2.

Peng, Xinwen; Liu, Peiwen; Pang, Bo; Yao, Yawen; Wang, Jiaxiu; Zhang, Kai published the artcile< Facile fabrication of pH-responsive nanoparticles from cellulose derivatives via Schiff base formation for controlled release>, Product Details of C30H36N4O2, the main research area is pH responsive nanoparticle cellulose derivative controlled drug release; Controlled release; Nanoparticles; Schiff base linkage; pH-stimuli responsiveness.

A controllable drug delivery system demonstrates a promising tool for diverse biomedical applications. In this work, a group of amphiphilic macromols. was designed and prepared via Schiff base reactions between 2,3-dialdehyde cellulose (DAC) with oleylamine and amino-containing compounds Benefiting from the self-assemble process of these amphiphilic macromols. in the poor solvent, a group of novel pH-responsive nanoparticles (NPs) were facilely fabricated by using nanopptn. dropping technique. The high amount of aldehyde groups on DAC chains enabled immobilization of tunable amounts of amine compounds (up to 1.67 mmol/g) in the NPs. Furthermore, the Schiff base bonds in NPs allowed the efficient release of the drug in acidic tumor microenvironment by cleaving the Schiff base linkages. This study demonstrates the formation of a group of novel pH-sensitive and drug-loadable NPs, which provide a simple and efficient drug delivery system for the potential application for cancer treatment.

Carbohydrate Polymers published new progress about Antitumor agents. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Product Details of C30H36N4O2.

Bowroju, Suresh K’s team published research in Molecules in 2020 | 399-76-8

Molecules published new progress about Alzheimer disease. 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Electric Literature of 399-76-8.

Bowroju, Suresh K.; Mainali, Nirjal; Ayyadevara, Srinivas; Penthala, Narsimha R.; Krishnamachari, Sesha; Kakraba, Samuel; Reis, Robert J. Shmookler; Crooks, Peter A. published the artcile< Design and synthesis of novel hybrid 8-hydroxy quinoline-indole derivatives as inhibitors of Aβ self-aggregation and metal chelation-induced Aβ aggregation>, Electric Literature of 399-76-8, the main research area is hydroxyquinoline indole quinoline indolylpiperazine preparation amyloid beta42 aggregation neurotoxicity; Alzheimer’s disease; Aβ-aggregation; clioquinol analogues; hybrid 8-hydroxyquinoline-indole analogs; metal chelating agents.

A series of novel hybrid 8-hydroxyquinoline-indole derivatives I (X = H, Cl; R = H, OMe, F), II (R = H, OMe), III (X = H, Cl, Br; R = H, OMe, F) were synthesized and screened for inhibitory activity against self-induced and metal-ion induced Aβ1-42 aggregation as potential treatments for Alzheimer’s disease (AD). In vitro studies identified the most inhibitory compounds against self-induced Aβ1-42 aggregation as III (X = Cl; R = H), III (X = H; R = OMe) and III (X = Cl; R = OMe) (EC50 = 1.72, 1.48 and 1.08μM, resp.) compared to the known anti-amyloid drug, clioquinol (EC50 = 9.95μM). The fluorescence of thioflavin T-stained amyloid formed by Aβ1-42 aggregation in the presence of Cu2+ or Zn2+ ions was also dramatically decreased by treatment with III (X = H, Cl; R = H, OMe). The most potent hybrid III (X = Cl; R = OMe) afforded 82.3% and 88.3% inhibition, resp., against Cu2+- induced and Zn2+- induced Aβ1-42 aggregation. Compounds III (X = H, Cl; R = H, OMe) were shown to be effective in reducing protein aggregation in HEK-tau and SY5Y-APPSw cells. Mol. docking studies with the most active compounds performed against Aβ1-42 peptide indicated that the potent inhibitory activity of compounds III (X = H, Cl; R = OMe) were predicted to be due to hydrogen bonding interactions, π-π stacking interactions and π-cation interactions with Aβ1-42, which may inhibit both self-aggregation as well as metal ion binding to Aβ1-42 to favor the inhibition of Aβ1-42 aggregation.

Molecules published new progress about Alzheimer disease. 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Electric Literature of 399-76-8.

Xu, Hui’s team published research in Chemical Biology & Drug Design in 2011-11-30 | 4771-48-6

Chemical Biology & Drug Design published new progress about Agrochemical fungicides. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Product Details of C10H9NO.

Xu, Hui; Yang, Wen-bin; Wang, Qin published the artcile< Antifungal agents. Part 3. Synthesis and antifungal activities of 3-acylindole analogs against phytopathogenic fungi in vitro>, Product Details of C10H9NO, the main research area is acylindole preparation agricultural fungicide; indole acyl preparation agricultural fungicide.

To find more potent antifungal compounds, twenty 3-acylindole analogs were synthesized and bio-evaluated for their antifungal activities against seven phytopathogenic fungi. Structure-activity relationships investigations revealed that 4- or 6-Me and 3-acetyl or propionyl groups were the important structural properties of 3-acylindoles for the activities. Especially 4-methyl-3-propionylindole, displayed the more potent activities than hymexazol, a com. available agricultural fungicide, and might be considered as a new promising lead candidate for further design and synthesis of agricultural fungicides.