04/01/2023 - Page 10 of 11 - Indole Building Blocks

Bandi, Madhu et al. published their research in Journal of Heterocyclic Chemistry in 2017 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Application In Synthesis of 5-Chloroindole-3-carboxaldehyde

One-Pot, Step-Wise, Alternative Syntheses of Quinoline-Substituted Bis(Indolyl)Methanes Using a Green Approach was written by Bandi, Madhu;Ch., Venkata Ramana Reddy. And the article was included in Journal of Heterocyclic Chemistry in 2017.Application In Synthesis of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

A green and highly efficient protocol for one-pot, step-wise, alternative syntheses of quinoline-substituted bis(indolyl)methanes has been described by the condensation of N-Me or N-Et quinolone-4-one-3-carbaldehydes with indoles in water containing a catalytic amount of L-proline to afford the title compounds, e.g., I, in high yields and in shorter reaction times. This reaction involves easy workup without using column chromatog. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Application In Synthesis of 5-Chloroindole-3-carboxaldehyde).

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

Xiao, Xiong et al. published their research in Tetrahedron Letters in 2014 | CAS: 210345-56-5

Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.HPLC of Formula: 210345-56-5

CuI-catalyzed intramolecular cyclization of 3-(2-aminophenyl)-2-bromoacrylate: synthesis of 2-carboxyindoles was written by Xiao, Xiong;Chen, Tian-Qi;Ren, Jiangmeng;Chen, Wei-Dong;Zeng, Bu-Bing. And the article was included in Tetrahedron Letters in 2014.HPLC of Formula: 210345-56-5 This article mentions the following:

A new approach was described for the synthesis of substituted 2-indolecarboxylates using 3-(2-aminophenyl)-2-bromoacrylates through a CuI-catalyzed intramol. coupling. The reactions were mild, rapid, and with good to excellent yields. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5HPLC of Formula: 210345-56-5).

Young, J. T. et al. published their research in Langmuir in 1996 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Related Products of 14204-27-4

Molecular Structure of Monolayers from Thiol-Terminated Polyimide Model Compounds on Gold. 1. A Spectroscopic Investigation was written by Young, J. T.;Boerio, F. J.;Zhang, Z.;Beck, T. L.. And the article was included in Langmuir in 1996.Related Products of 14204-27-4 This article mentions the following:

The mol. orientation and/or packing for monolayers formed by adsorption of (4-mercaptophenyl)phthalimide (4-MPP), a thiol-terminated polyimide model compound, onto gold substrates, was determined using surface-enhanced Raman scattering (SERS), reflection-absorption IR spectroscopy (RAIR), XPS (XPS), ellipsometry, and electrochem. SERS, RAIR, and XPS showed that 4-MPP mols. were chemisorbed onto the gold surface through the thiol groups to form an oriented monolayer. For adsorption times less than about 2 h, the ellipsometric thickness of the films increased as a function of time, but for longer times the ellipsometric thickness reached a limiting value of about 11.5 Å. For adsorption times greater than about 2 h, the surface d. was about 5.2 × 10^-10 mol/cm², corresponding to a mol. area of 32 Å²/mol. Considering the size of the 4-MPP mol. compared to that of an alkanethiol mol., it was concluded that the adsorbed mols. were highly packed on the gold surface. The orientation of adsorbed 4-MPP mols. was determined quant. using IR spectroscopy. It was found that the mols. were oriented with a vertical configuration in which the mol. axes tilted away from the surface normal by about 21°. There was no preferred rotation angle for the imide ring in 4-MPP. The thickness and orientation determined by IR spectroscopy were in excellent agreement with results obtained from mol. dynamics, which are presented in the following paper. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Related Products of 14204-27-4).

Wu, Jia-Hong et al. published their research in Organic Letters in 2020 | CAS: 774-47-0

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Quality Control of 5,6-Difluoroindoline-2,3-dione

Enantioselective Synthesis of Multifunctionalized 4H-Pyrans via Formal [4 + 2] Annulation Process by Bifunctional Phosphonium Salt Catalysis was written by Wu, Jia-Hong;Pan, Jianke;Du, Juan;Wang, Xiaoxia;Wang, Xuemei;Jiang, Chunhui;Wang, Tianli. And the article was included in Organic Letters in 2020.Quality Control of 5,6-Difluoroindoline-2,3-dione This article mentions the following:

A highly enantioselective formal [4 + 2] annulation involving electron-deficient allenes as C2-synthons has been developed under bifunctional phosphonium salt catalysis. With this catalytic protocol, a wide range of synthetically interesting and highly functionalized chiral 4H-pyran derivatives were readily prepared in good yields (up to 99%) with outstanding diastereo- and enantioselectivities (up to >20:1 dr, up to >99.9% ee). The utility and the practicality of this method were demonstrated by the gram-scale reaction and facile elaboration. Of note, this is the first example of an asym. annulation reaction involving allenic reactants under a phase-transfer catalysis system. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Quality Control of 5,6-Difluoroindoline-2,3-dione).

Wei, Zhaoxin et al. published their research in European Journal of Organic Chemistry in 2021 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Recommanded Product: 14204-27-4

Electrochemical Direct Thiolation of Lactams with Mercaptans: An Efficient Access to N-Acylsulfenamides was written by Wei, Zhaoxin;Wang, Renjie;Zhang, Yonghong;Wang, Bin;Xia, Yu;Abdukader, Ablimit;Xue, Fei;Jin, Weiwei;Liu, Chenjiang. And the article was included in European Journal of Organic Chemistry in 2021.Recommanded Product: 14204-27-4 This article mentions the following:

An efficient and eco-friendly electrochem. methodol. for the oxidative cross coupling hydrogen evolution (CCHE) reactions of lactams with thiols was presented. Various electron deficient N-acylsulfenamides were smoothly produced in modest to excellent yields without using any external oxidant. Elementary mechanistic insight supported a possible free radical process and hydrogen was the only side product. The approach provided a safe, convenient, and economical preparation of synthetically important N-thiophthalimides on a gram scale. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Recommanded Product: 14204-27-4).

Thatikonda, Thanusha et al. published their research in Organic Letters in 2019 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Category: indole-building-block

α-Angelica Lactone in a New Role: Facile Access to N-Aryl Tetrahydroisoquinolinones and Isoindolinones via Organocatalytic α-CH₂ Oxygenation was written by Thatikonda, Thanusha;Deepake, Siddharth K.;Das, Utpal. And the article was included in Organic Letters in 2019.Category: indole-building-block This article mentions the following:

A method for the direct oxidation of various N-aryl tetrahydroisoquinolines and isoindolines to the corresponding lactams using α-angelica lactone as a catalyst was developed. The utility of the method was further demonstrated by synthesis of indoprofen and indobufen. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Category: indole-building-block).

Yang, Tianbao et al. published their research in Organic Letters in 2020 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Electric Literature of C8H6N2O2

CF₃SO₂Na-Mediated, UV-Light-Induced Friedel-Crafts Alkylation of Indoles with Ketones/Aldehydes and Bioactivities of Products was written by Yang, Tianbao;Lu, Huiai;Shu, Yixuan;Ou, Yifeng;Hong, Ling;Au, Chak-Tong;Qiu, Renhua. And the article was included in Organic Letters in 2020.Electric Literature of C8H6N2O2 This article mentions the following:

A concise, one-step route to produce 3,3′-diindolylmethanes (DIMs) from simple indoles and ketones or aldehydes is reported. The key step is the ready formation of indole derivatives that involves the in situ conversion of CF₃SO₂Na reagent to ·CF₃ under oxygen or air (1.0 atm) and UV irradiation It is disclosed that most of the obtained DIMs show anticancer activities in human bladder cancer cell lines EJ and T24. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Electric Literature of C8H6N2O2).

Thumser, Stefan et al. published their research in Journal of the American Chemical Society in 2021 | CAS: 774-47-0

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.COA of Formula: C8H3F2NO2

All-Red-Light Photoswitching of Indirubin Controlled by Supramolecular Interactions was written by Thumser, Stefan;Koettner, Laura;Hoffmann, Nadine;Mayer, Peter;Dube, Henry. And the article was included in Journal of the American Chemical Society in 2021.COA of Formula: C8H3F2NO2 This article mentions the following:

Red-light responsiveness of photoswitches is a highly desired property for many important application areas such as biol. or material sciences. The main approach to elicit this property uses strategic substitution of long-known photoswitch motives such as azobenzenes or diarylethenes. Only very few photoswitches possess inherent red-light absorption of their core chromophore structures. Here, author present a strategy to convert the long-known purple indirubin dye into a prolific red-light-responsive photoswitch. In a supramol. approach, its photochromism can be changed from a neg. to a pos. one, while at the same time, significantly higher yields of the metastable E-isomer are obtained upon irradiation E- to Z-photoisomerization can then also be induced by red light of longer wavelengths. Indirubin therefore represents a unique example of reversible photoswitching using entirely red light for both switching directions. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0COA of Formula: C8H3F2NO2).

Sreenatha, Vasappanavara et al. published their research in Indian Journal of Chemistry in 2021 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. 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. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Reference of 827-01-0

Synthesis and structural confirmation on selective N-alkylation of (Z)-5-((5-chloro-1H-indol-3-yl)methylene)thiazolidine-2,4-dione analogues with their molecular docking studies was written by Sreenatha, Vasappanavara;Prasad, Karnam Jayarampillai Rajendra. And the article was included in Indian Journal of Chemistry in 2021.Reference of 827-01-0 This article mentions the following:

In the present investigation, a series of novel (Z)-5-((5-chloro-1H-indol-3-yl)methylene)thiazolidine-2,4-dione analogs had been designed and synthesized in good yields with the objective of selective N-alkylation at thiazolidine 2,4-dione ring in competence with indole ring under basic conditions in the presence of aprotic solvent DMF. The newly synthesized compounds have been characterized by spectral data (IR, ¹H and ¹³C NMR, NOE, NOESY, ¹H-¹H-COSY and LC-MS). Further, mol. docking and ADME studies had revealed that the newly synthesized compounds have very good docking score against antidiabetic and anti-inflammation activities (PPARy and COX-2) as compared with standard rosiglitazone. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Reference of 827-01-0).

Ozdemir, Ahmet et al. published their research in European Journal of Medicinal Chemistry in 2015 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Recommanded Product: 827-01-0

Synthesis and evaluation of new indole-based chalcones as potential antiinflammatory agents was written by Ozdemir, Ahmet;Altintop, Mehlika Dilek;Turan-Zitouni, Gulhan;Ciftci, Gulsen Akalin;Ertorun, Ipek;Alatas, Ozkan;Kaplancikli, Zafer Asim. And the article was included in European Journal of Medicinal Chemistry in 2015.Recommanded Product: 827-01-0 This article mentions the following:

In the present work, new indole-based chalcone derivatives were obtained via the reaction of 5-substituted-1H-indole-3-carboxaldehydes/1-methylindole-3-carboxaldehyde with appropriate acetophenones. The synthesized compounds were studied for their in vitro COX-1 and COX-2 inhibitory activity. The most effective COX inhibitors were also evaluated for their in vivo antiinflammatory and antioxidant activities in LPS induced sepsis model. Furthermore, the CCK-8 assay was carried out to determine cytotoxic effects of all compounds against NIH/3T3 mouse embryonic fibroblast cells. 3-(5-Bromo-1H-indol-3-yl)-1-(4-cyanophenyl)prop-2-en-1-one (6) can be considered as a non-selective COX inhibitor (COX-1 IC₅₀ = 8.1 ± 0.2 μg/mL, COX-2 IC₅₀ = 9.5 ± 0.8 μg/mL), whereas 3-(5-methoxy-1H-indol-3-yl)-1-(4-(methylsulfonyl)phenyl)prop-2-en-1-one (1) inhibited only COX-1 (IC₅₀ = 8.6 ± 0.1 μg/mL). According to in vivo studies, these compounds also displayed antiinflammatory and antioxidant activities. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Recommanded Product: 827-01-0).