Indole Building Blocks

Identification of potentially anti-COVID-19 active drugs using the connectivity MAP was written by Bonnet, Raphael;Mariault, Lee;Peyron, Jean-Francois. And the article was included in PLoS One in 2022.Recommanded Product: 280744-09-4 This article mentions the following:

Drug repurposing can be an interesting strategy for an emergency response to the severe acute respiratory syndrome-coronavirus-2, (SARS-COV-2), the causing agent of the coronavirus disease-19 (COVID-19) pandemic. For this, we applied the Connectivity Map (CMap) bioinformatic resource to identify drugs that generate, in the CMap database, gene expression profiles (GEP) that neg. correlate with a SARS-COV-2 GEP, anticipating that these drugs could antagonize the deleterious effects of the virus at cell, tissue or organism levels. We identified several anti-cancer compounds that target MDM2 in the p53 pathway or signaling proteins: Ras, PKB尾, Nitric Oxide synthase, Rho kinase, all involved in the transmission of proliferative and growth signals. We hypothesized that these drugs could interfere with the high rate of biomass synthesis in infected cells, a feature shared with cancer cells. Other compounds including etomoxir, triacsin-c, PTB1-IN-3, are known to modulate lipid metabolism or to favor catabolic reactions by activating AMPK. Four different anti-inflammatory mols., including dexamethasone, fluorometholone and cytosporone-b, targeting the glucocorticoid receptor, cyclooxygenase, or NUR77 also came out of the anal. These results represent a first step in the characterization of potential repositioning strategies to treat SARS-COV-2. In the experiment, the researchers used many compounds, for example, 3-(2,4-Dichlorophenyl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione (cas: 280744-09-4Recommanded Product: 280744-09-4).

3-(2,4-Dichlorophenyl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione (cas: 280744-09-4) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Recommanded Product: 280744-09-4

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

Electrochemical behavior of N-oxyphthalimides: Cascades initiating self-sustaining catalytic reductive N-O bond cleavage was written by Syroeshkin, Mikhail A.;Krylov, Igor B.;Hughes, Audrey M.;Alabugin, Igor V.;Nasybullina, Darya V.;Sharipov, Mikhail Yu.;Gultyai, Vadim P.;Terent’ev, Alexander O.. And the article was included in Journal of Physical Organic Chemistry in 2017.Product Details of 58585-84-5 This article mentions the following:

N-oxyphthalimides are stable and easily accessible compounds that can produce O radicals upon 1-electron reduction The authors present a systematic study of electrochem. properties of N-oxyphthalimide derivatives (PI-ORs) in DMF by cyclic voltammetry. In all cases, electron transfer to the substrate leads to decomposition of the intermediate radical anion via the N-O bond cleavage. In the case of benzyloxyphthalimide or its derivatives containing electron-donating substituents, reductive electron transfer induces the chain decomposition of the substrate to phthalimide (PI) radical-anion and the corresponding carbonyl compound The PI radical-anion product is a powerful reductant that can transfer an electron to the reactant PI-OR, thus establishing a catalytic cycle for reductive N-O scission. This self-catalytic process is reflected in a considerable decrease in the reduction current for the substrate (<1e^–/mol.). By contrast, reductive fragmentations of benzyl derivatives containing electron-withdrawing substituents in the aromatic ring or at the benzylic position, as well as tosyl and alkyl derivatives, occur via a 1-electron mechanism. A sequence of N-O and C-C scissions was engineered to support the intermediacy of O-centered radicals in these processes. In the experiment, the researchers used many compounds, for example, 1,3-Dioxoisoindolin-2-yl benzoate (cas: 58585-84-5Product Details of 58585-84-5).

1,3-Dioxoisoindolin-2-yl benzoate (cas: 58585-84-5) 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.Product Details of 58585-84-5

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

Molybdenum-Catalyzed Intermolecular Deoxygenative Cross-Coupling Reactions of 1,2-Diketones with 伪-Ketoamides was written by Dong, Yuan-Qing;Wang, Kai;Zhuo, Chun-Xiang. And the article was included in ACS Catalysis in 2022.COA of Formula: C8H6N2O2 This article mentions the following:

The Mo-catalyzed intermol. deoxygenative cross coupling of the bench stable and readily accessible 1,2-diketones R¹C(O)C(O)R² (R¹ = Ph, Me, 4-MeOC₆H₄, etc.; R² = Ph, Me, 4-Co₂Me-C₆H₄, etc.) with 伪-ketoamides R³NHC(O)C(O)R⁴ (R³ = Ph, cyclohexyl, naphthalen-2-yl, etc.; R⁴ = Ph, 3-methoxyphenyl, thiophen-3-yl, etc.), in which three of the four carbonyl oxygen atoms were eliminated along with the formations of a carbon-nitrogen bond and a carbon-carbon double bond in one step under Mo-catalysis was described. Various pyrrol-2-ones I were secured in up to 96% yield by utilizing a com. Mo-catalyst. The synthetic potential of the current methodol. is addnl. demonstrated by synthetic transformations, a gram-scale synthesis, and derivatization of several natural products and drug mols. The preliminary mechanistic investigation suggests that cascade process might be initiated via the formal intermol. N-H insertion and followed by the intramol. carbonyl-carbonyl olefination reaction, in which both steps were catalyzed by a single Mo-catalyst. In the experiment, the researchers used many compounds, for example, 4-Nitroindole (cas: 4769-97-5COA of Formula: C8H6N2O2).

4-Nitroindole (cas: 4769-97-5) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.COA of Formula: C8H6N2O2

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

Synthesis of New Fluorogenic Cyanine Dyes and Incorporation into RNA Fluoromodules was written by Constantin, Tudor P.;Silva, Gloria L.;Robertson, Kelly L.;Hamilton, Tamara P.;Fague, Kaitlin;Waggoner, Alan S.;Armitage, Bruce A.. And the article was included in Organic Letters in 2008.HPLC of Formula: 171429-43-9 This article mentions the following:

A new fluorogenic cyanine dye was synthesized and found to have low fluorescence quantum yield in fluid solution and in the presence of double-stranded DNA but 80-fold enhanced fluorescence in viscous glycerol solution An RNA aptamer selected for binding to the new dye exhibits K_d = 87 nM and 60-fold fluorescence enhancement. The dye-aptamer pair is a fluoromodule that can be incorporated into fluorescent sensors and labels. In the experiment, the researchers used many compounds, for example, 1-(5-Carboxypentyl)-2,3,3-trimethyl-3H-indol-1-ium bromide (cas: 171429-43-9HPLC of Formula: 171429-43-9).

1-(5-Carboxypentyl)-2,3,3-trimethyl-3H-indol-1-ium bromide (cas: 171429-43-9) 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.HPLC of Formula: 171429-43-9

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

Diazine Indole Acetic Acids as Potent, Selective, and Orally Bioavailable Antagonists of Chemoattractant Receptor Homologous Molecule Expressed on Th2 Cells (CRTH2) for the Treatment of Allergic Inflammatory Diseases was written by Kaila, Neelu;Huang, Adrian;Moretto, Alessandro;Follows, Bruce;Janz, Kristin;Lowe, Michael;Thomason, Jennifer;Mansour, Tarek S.;Hubeau, Cedric;Page, Karen;Morgan, Paul;Fish, Susan;Xu, Xin;Williams, Cara;Saiah, Eddine. And the article was included in Journal of Medicinal Chemistry in 2012.Recommanded Product: 19017-52-8 This article mentions the following:

New classes of CRTH2 antagonists, the pyridazine linker containing indole acetic acids, are described. The initial hit I had good potency but poor permeability, metabolic stability, and PK. Initial optimization led to compounds of type I with low oxidative metabolism but poor oral bioavailability. Poor permeability was identified as a liability for these compounds Addition of a linker between the indole and diazine moieties afforded a series with good potency, low rates of metabolism, moderate permeability, and good oral bioavailability in rodents. III was identified as the development track candidate. It was potent in cell based, binding, and whole blood assays and exhibited good PK profile. It was efficacious in mouse models of contact hypersensitivity (1 mg/kg b.i.d.) and house dust (20 mg/kg q.d.) when dosed orally. In sheep asthma, administration at 1 mg/kg iv completely blocked the LAR and AHR and attenuated the EAR phase. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-2-methyl-1H-indol-3-yl)acetic acid (cas: 19017-52-8Recommanded Product: 19017-52-8).

2-(5-Chloro-2-methyl-1H-indol-3-yl)acetic acid (cas: 19017-52-8) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Recommanded Product: 19017-52-8

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

Reply to ‘Sulfisoxazole does not inhibit the secretion of small extracellular vesicles’ was written by Lee, Chan-Hyeong;Bae, Ju-Hyeon;Kim, Jong-In;Park, Ju-Mi;Choi, Eun-Ji;Baek, Moon-Chang. And the article was included in Nature Communications in 2021.Name: 2-((3R,6S,9R,12R,17aS)-9-((1H-Indol-3-yl)methyl)-6-isobutyl-3-isopropyl-1,4,7,10,13-pentaoxohexadecahydro-1H-pyrrolo[1,2-a][1,4,7,10,13]pentaazacyclopentadecin-12-yl)acetic acid This article mentions the following:

The study discussed on reply on the statement ‘Sulfisoxazole that does not inhibit the secretion of small extracellular vesicles’. The evidences came from the number of sEVs based on nano-particle tracking anal. (NTA) results, the protein amount of sEVs, and electron microscopy. In addition, we identified the target of SFX, endothelin receptor A (ETA). Inhibitors of ETA, including zibotentan, BQ123, and PD156707, also inhibited the secretion of sEVs from MDA-MB231 cells. Furthermore, the knockdown of ETA with an ETA short hairpin RNA significantly decreased the secretion of sEVs. Collectively, it was showed the inhibition of sEV secretion from MDA-MB231 via ETA through pharmacol. and genetic approaches. Collectively, these results show that SFX does inhibit the secretion of small extracellular vesicles in our experiments In the experiment, the researchers used many compounds, for example, 2-((3R,6S,9R,12R,17aS)-9-((1H-Indol-3-yl)methyl)-6-isobutyl-3-isopropyl-1,4,7,10,13-pentaoxohexadecahydro-1H-pyrrolo[1,2-a][1,4,7,10,13]pentaazacyclopentadecin-12-yl)acetic acid (cas: 136553-81-6Name: 2-((3R,6S,9R,12R,17aS)-9-((1H-Indol-3-yl)methyl)-6-isobutyl-3-isopropyl-1,4,7,10,13-pentaoxohexadecahydro-1H-pyrrolo[1,2-a][1,4,7,10,13]pentaazacyclopentadecin-12-yl)acetic acid).

2-((3R,6S,9R,12R,17aS)-9-((1H-Indol-3-yl)methyl)-6-isobutyl-3-isopropyl-1,4,7,10,13-pentaoxohexadecahydro-1H-pyrrolo[1,2-a][1,4,7,10,13]pentaazacyclopentadecin-12-yl)acetic acid (cas: 136553-81-6) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Name: 2-((3R,6S,9R,12R,17aS)-9-((1H-Indol-3-yl)methyl)-6-isobutyl-3-isopropyl-1,4,7,10,13-pentaoxohexadecahydro-1H-pyrrolo[1,2-a][1,4,7,10,13]pentaazacyclopentadecin-12-yl)acetic acid

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

A highly sensitive fluorescent probe that quantifies transthyretin in human plasma as an early diagnostic tool of Alzheimer’s disease was written by Lim, Hye Rim;Kim, Seo Yun;Jeon, Eun Hee;Kim, Yun Lan;Shin, Yu Mi;Koo, Tae-Sung;Park, Sung Jean;Hong, Ki Bum;Choi, Sungwook. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2019.Safety of 2,3,3-Trimethyl-3H-indol-5-amine This article mentions the following:

The development of sensitive and reliable fluorescent probes for the early diagnosis of Alzheimer’s disease (AD) is highly challenging and plays an important role in achieving effective treatments. Herein, we designed and synthesized an indole-based fluorophore for TTR in human plasma, an important hallmark of AD pathogenesis. This robust and simple fluorescent method allows quantification of TTR in the complex biol. matrix. In the experiment, the researchers used many compounds, for example, 2,3,3-Trimethyl-3H-indol-5-amine (cas: 773-63-7Safety of 2,3,3-Trimethyl-3H-indol-5-amine).

2,3,3-Trimethyl-3H-indol-5-amine (cas: 773-63-7) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Safety of 2,3,3-Trimethyl-3H-indol-5-amine

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

Synthesis of (Z)-5-[(5-(2-(phenylsulfonyl-ethyl)-1H-indol-3-yl)methylene]thiazolidine-2,4-dione of potential pharmacological interest was written by Laxminarayana, Keetha;Rajendiran, Chinnapillai;Mukkanti, Khagga. And the article was included in Asian Journal of Chemistry in 2013.HPLC of Formula: 10102-94-0 This article mentions the following:

Formylation of 5-bromo-1H-indole under Vilsmeier-Hack formylation conditions using POCl₃ and DMF as a reagents under cooling conditions (0-5掳) followed by a simple process gave 5-bromo-1H-indole-3-carboxaldehyde. A condensation reaction of this aldehyde with 2,4-thiazolidinedione in toluene as a solvent in the presence of PTSA and TBAB as a phase transfer catalyst under stirring at room temperature for 10-30 min, then slowly raising the temperature to 105掳 and maintaining for 12-15 h gave (Z)-5-[(5-bromo-1-alkyl-1H-indol-3-yl)methylene]-2,4-thiazolidinedione. Further condensation of this intermediate with phenyl(vinyl)sulfone in the presence of palladium acetate as a catalyst and DMF as a solvent and heating to 100-105掳 for 16 h gave (5Z)-5-[1-alkyl-5-[(E)-2-[(phenylsulfonyl)vinyl]-1H-indol-3-yl]methylene]-2,4-thiazolidinedione derivatives Reduction of this compound in the presence of hydrogen gas, palladium-carbon as a catalyst in acetic acid medium and methanol as a solvent heating at 45-50掳 for 8 h gave (Z)-5-[1-alkyl-5-[2-[2-(phenylsulfonyl)ethyl]-1H-indol-3-yl]methylene]-2,4-thiazolidinedione derivatives These products could also be prepared by an alternate route and the products were characterized on the basis of spectral and anal. data. The title compounds thus formed included a thiazolidinedione indole sulfone (I). In the experiment, the researchers used many compounds, for example, 5-Bromo-1-methyl-1H-indole-3-carbaldehyde (cas: 10102-94-0HPLC of Formula: 10102-94-0).

5-Bromo-1-methyl-1H-indole-3-carbaldehyde (cas: 10102-94-0) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.HPLC of Formula: 10102-94-0

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

Regiochemistry of the microwave-assisted reaction between aromatic amines and 伪-bromo ketones to yield substituted 1H-indoles was written by Vara, Yosu;Aldaba, Eneko;Arrieta, Ana;Pizarro, Jose L.;Arriortua, Maria I.;Cossio, Fernando P.. And the article was included in Organic & Biomolecular Chemistry in 2008.Recommanded Product: 776-41-0 This article mentions the following:

The scope and regioselectivity of the Bischler (or Bischler-Moehlau) reaction between aromatic amines and 伪-bromo ketones has been studied by computational and exptl. techniques. It has been found that in many cases the reaction yields are improved under microwave irradiation and working in the absence of solvent. When di- and trisubstituted amines are used as substrates the regioselectivity of the reaction is different to that obtained with primary anilines. The reaction between benzene-1,2-diamine and 伪-bromoacetophenones under the same conditions yields 2-substituted quinoxalines instead of indoles. Finally, when pyridin-2-amines and pyrimidin-2-amines are allowed to react with 伪-bromoacetophenones, imidazo[1,2-a]pyridines and imidazo[1,2-a]pyrimidines are obtained. In the experiment, the researchers used many compounds, for example, Ethyl 1H-indole-3-carboxylate (cas: 776-41-0Recommanded Product: 776-41-0).

Ethyl 1H-indole-3-carboxylate (cas: 776-41-0) 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: 776-41-0

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

Visible-Light-Initiated One-Pot, Three-Component Synthesis of 2-Amino-4H-pyran-3,5-dicarbonitrile Derivatives was written by Zhang, Mo;Chen, Meng-Nan;Li, Jiao-Mian;Liu, Nan;Zhang, Zhan-Hui. And the article was included in ACS Combinatorial Science in 2019.Application of 20780-72-7 This article mentions the following:

A novel approach for the visible-light-initiated synthesis of 2-amino-4H-pyran-3,5-dicarbonitrile derivatives via a one-pot, three-component reaction of aldehydes or isatins, malononitrile, and 伪-cyano ketones was developed. The reaction was carried out at room temperature in ethanol/water to give the corresponding products with a wide range of functional groups in high yields. This process did not require any additives or chromatog. separation and could be applied for gram-scale synthesis. In the experiment, the researchers used many compounds, for example, 4-Bromoindoline-2,3-dione (cas: 20780-72-7Application of 20780-72-7).

4-Bromoindoline-2,3-dione (cas: 20780-72-7) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. 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). Application of 20780-72-7

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