05/01/2023 - Page 4 of 11 - Indole Building Blocks

Audubert, Clement et al. published their research in Angewandte Chemie, International Edition in 2017 | CAS: 167631-84-7

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.COA of Formula: C10H8FNO2

Batch and Continuous-Flow One-Pot Processes using Amine Diazotization to Produce Silylated Diazo Reagents was written by Audubert, Clement;Gamboa Marin, Oscar Javier;Lebel, Helene. And the article was included in Angewandte Chemie, International Edition in 2017.COA of Formula: C10H8FNO2 This article mentions the following:

A novel synthesis of trimethylsilyldiazomethane (TMSCHN₂) by diazotization of trimethylsilylmethylamine (TMSCH₂NH₂) is reported using batch and continuous flow syntheses. The latter affords a daily production of 275 g (2.4 mol) of TMSCHN₂. Other silylated methylamines were also successfully reacted under the developed reaction conditions to furnish various silicon-bearing diazomethane reagents. The applicability of the process is highlighted by disclosure of batch and continuous flow one-pot esterification and 1,3-dipolar cycloaddition processes. Furthermore, the high-yielding esterification of carboxylic acids with silylated and substituted methylamines in continuous flow is disclosed. Finally, work-up and purification procedures are reported for the preparation of a 2-MeTHF solution of TMSCHN₂, which can be used in rhodium-catalyzed methylenation and homologation reactions. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7COA of Formula: C10H8FNO2).

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

Ramachandran, Sreekanth A. et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2017 | CAS: 754214-56-7

7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7) 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: 7-Azaindole-5-boronic Acid Pinacol Ester

Discovery of pyrazolopyrimidine derivatives as novel inhibitors of ataxia telangiectasia and rad3 related protein (ATR) was written by Ramachandran, Sreekanth A.;Jadhavar, Pradeep S.;Singh, Manvendra P.;Sharma, Ankesh;Bagle, Gaurav N.;Quinn, Kevin P.;Wong, Po-yin;Protter, Andrew A.;Rai, Roopa;Pham, Son M.;Lindquist, Jeffrey N.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2017.Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester This article mentions the following:

The ATR pathway is a critical mediator of the replication stress response in cells. In aberrantly proliferating cancer cells, this pathway can help maintain sufficient genomic integrity for cancer cell progression. Herein the authors describe the discovery of 1-(4-(methylsulfonyl)phenyl)-3-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, a pyrazolopyrimidine-containing inhibitor of ATR via a strategic repurposing of compounds targeting PI3K. In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester).

Forbes, Ian T. et al. published their research in Journal of Medicinal Chemistry in 1993 | CAS: 85696-95-3

1-Methyl-1H-indol-4-amine (cas: 85696-95-3) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Related Products of 85696-95-3

N-(1-Methyl-5-indolyl)-N’-(3-pyridyl)urea hydrochloride: the first selective 5-HT_1C receptor antagonist was written by Forbes, Ian T.;Kennett, Guy A.;Gadre, Angela;Ham, Peter;Hayward, Clare J.;Martin, Roger T.;Thompson, Mervyn;Wood, Martyn D.;Baxter, Gordon S.. And the article was included in Journal of Medicinal Chemistry in 1993.Related Products of 85696-95-3 This article mentions the following:

Development of specific 5-HT_1C receptor antagonists has been impeded by the marked similarity between this site and the 5-HT₂ receptor. A series of pyridyl indolyl ureas I (4-, 5-, 6-, 7-NHCOCNHR¹; R¹ = 3-pyridyl) were synthesized and shown to have affinity for the 5-HT_1C receptor. One of these, I (R = 5-NHCONHR¹, R¹ = 3-pyridyl)(II) shows ≥48 fold selectivity in ligand binding studies for the 5-HT_1C (pK_I = 6.86) over the 5-HT₂, 5-HT_1A, 5-HT_1D, 5-HT₃, adrenergic α₁, α_2A, α_2B, β₁, β₂, dopaminergic D₁, and D₂ receptors. II is a silent, competitive antagonist of 5-HT-stimulated phosphoinositide hydrolysis in the pig choroid plexus (pK_B = 7.03), a model of 5-HT_1C receptor functional activity and was also a surmountable antagonist of the 5-HT_1C-like receptor in the rat stomach fundus (pA₂ = 7.52). Thus, II represents the first reported selective 5-HT_1C receptor antagonist. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-indol-4-amine (cas: 85696-95-3Related Products of 85696-95-3).

Pang, Yuan-Ping et al. published their research in Journal of the American Chemical Society in 1999 | CAS: 6639-06-1

3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1) 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). Computed Properties of C11H11NO2

Computational and Experimental Studies of (2,2)-Bis(indol-1-yl-methyl)acetate Suggest the Importance of the Hydrophobic Effect in Aromatic Stacking Interactions was written by Pang, Yuan-Ping;Miller, Jennifer L.;Kollman, Peter A.. And the article was included in Journal of the American Chemical Society in 1999.Computed Properties of C11H11NO2 This article mentions the following:

To understand the driving forces of aromatic stacking interactions in water, we have performed conformational searches, mol. dynamics simulations, potential of mean force (PMF) and free energy perturbation (FEP) calculations, syntheses, and NMR studies on sodium (2,2)-bis(indol-1-yl-methyl)acetate (1), sodium 3-indol-1-yl-2-methyl-propionate (2), and sodium 3-indol-1-yl-propionate (3). The conformational searches on 1 revealed that the isobutyric acid linker of 1 allows the mol. to adopt the tilted T-shaped stacked, off-center stacked, face-to-face stacked, and non-stacked conformations in a vacuum. The PMF and FEP calculations suggested that the most thermodynamically stable conformers in water are the tilted T-shaped stacked and non-stacked conformers. Independent NMR spectroscopic studies of 1-3 revealed that both the tilted T-shaped stacked and non-stacked conformers are populated in D₂O and in d₆-DMSO, and they are in a rapid equilibrium Furthermore, the NMR studies found (i) a larger population of the tilted T-shaped stacked conformation of 1 at 22 ° in D₂O than in d₆-DMSO and (ii) more different populated stacked conformations of 1 at 60° in D₂O than in d₆-DMSO. One would expect larger populations of the stacked conformations in d₆-DMSO, whose dielec. constant is smaller than that of water, if the electrostatic interaction were the only driving force of the aromatic stacking interactions. The results, therefore, suggest that the hydrophobic effect plays an important role in the stacking interaction of 1 in water. In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1Computed Properties of C11H11NO2).

Cai, Lu et al. published their research in Organic Letters in 2019 | CAS: 85696-95-3

1-Methyl-1H-indol-4-amine (cas: 85696-95-3) 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. 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.Reference of 85696-95-3

Chiral Phosphoric-Acid-Catalyzed Regioselective and Enantioselective C7-Friedel-Crafts Alkylation of 4-Aminoindoles with Trifluoromethyl Ketones was written by Cai, Lu;Zhao, Yunlong;Huang, Tongkun;Meng, Shanshui;Jia, Xian;Chan, Albert S. C.;Zhao, Junling. And the article was included in Organic Letters in 2019.Reference of 85696-95-3 This article mentions the following:

A highly regioselective and enantioselective C7-Friedel-Crafts alkylation of 4-aminoindoles with trifluoromethyl ketones promoted by a spirocyclic phosphoric acid was developed. This strategy was applicable to various substituted trifluoromethyl ketones and 4-aminoindole derivatives, affording the corresponding C7-functionalized indole derivatives, bearing a pharmaceutically interesting trifluoromethylated tertiary alc. scaffold, in 21%-98% yields with up to >99% enantiomeric excess (ee). In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-indol-4-amine (cas: 85696-95-3Reference of 85696-95-3).

Shen, Mengqi et al. published their research in Journal of the American Chemical Society in 2018 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) 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 was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Recommanded Product: 6-Nitro-1H-indole

Room-Temperature Chemoselective Reduction of 3-Nitrostyrene to 3-Vinylaniline by Ammonia Borane over Cu Nanoparticles was written by Shen, Mengqi;Liu, Hu;Yu, Chao;Yin, Zhouyang;Muzzio, Michelle;Li, Junrui;Xi, Zheng;Yu, Yongsheng;Sun, Shouheng. And the article was included in Journal of the American Chemical Society in 2018.Recommanded Product: 6-Nitro-1H-indole This article mentions the following:

We report a new strategy of controlling catalytic activity and selectivity of Cu nanoparticles (NPs) for the ammonia borane-initiated hydrogenation reaction. Cu NPs are active and selective for chemoselective reduction of nitrostyrene to vinylaniline under ambient conditions. Their activity, selectivity, and more importantly, stability are greatly enhanced by their anchoring on WO_2.72 nanorods, providing a room-temperature full conversion of nitrostyrene selectively to vinylaniline (>99% yield). Compared with all other catalysts developed thus far, our new Cu/WO_2.72 catalyst shows much enhanced hydrogenation selectivity and stability without the use of pressured hydrogen. The synthetic approach demonstrated here can be extended to prepare various M/WO_2.72 catalysts (M = Fe, Co, Ni), with M being stabilized for many chem. reactions. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Recommanded Product: 6-Nitro-1H-indole).

Sammaiah, G. et al. published their research in International Journal of Chemical Sciences in 2008 | CAS: 112656-95-8

7-Nitroindoline-2,3-dione (cas: 112656-95-8) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Safety of 7-Nitroindoline-2,3-dione

Anticancer and antioxidant activities of 2-aminobenzoic acid (2-oxo-1,2-dihydro-indol-3-ylidene) hydrazides was written by Sammaiah, G.;Narsaiah, N.;Krishnaveni, J.;Dayakar, G.;Sarangapani, M.. And the article was included in International Journal of Chemical Sciences in 2008.Safety of 7-Nitroindoline-2,3-dione This article mentions the following:

In this communication, the anticancer and antioxidant activities of some new 2-aminobenzoic acid (2-oxo-1,2-dihydro-indol-3-ylidene) hydrazides are presented. The new compounds were prepared by the condensation of indole-2,3-diones with 2-aminobenzoic acid hydrazide. All the compounds were evaluated for anticancer activity (against HeLa cell lines, IMR-32 cell lines) and antioxidant activity. Some of the compounds exhibited moderate anticancer activity against the cell lines employed and promising antioxidant activity. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Safety of 7-Nitroindoline-2,3-dione).

Murugesan, Kathiravan et al. published their research in Green Chemistry in 2018 | CAS: 90271-86-6

5-Bromo-3-cyanoindole (cas: 90271-86-6) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Recommanded Product: 5-Bromo-3-cyanoindole

Stable and reusable nanoscale Fe₂O₃-catalyzed aerobic oxidation process for the selective synthesis of nitriles and primary amides was written by Murugesan, Kathiravan;Senthamarai, Thirusangumurugan;Sohail, Manzar;Sharif, Muhammad;Kalevaru, Narayana V.;Jagadeesh, Rajenahally V.. And the article was included in Green Chemistry in 2018.Recommanded Product: 5-Bromo-3-cyanoindole This article mentions the following:

The sustainable introduction of nitrogen moieties in the form of nitrile or amide groups in functionalized mols. is of fundamental interest because nitrogen-containing motifs are found in a large number of life science mols., natural products and materials. Hence, the synthesis and functionalization of nitriles and amides from easily available starting materials using cost-effective catalysts and green reagents is highly desired. In this regard, herein the nanoscale iron oxide-catalyzed environmentally benign synthesis of nitriles and primary amides from aldehydes and aqueous ammonia in the presence of 1 bar O₂ or air was reported. Under mild reaction conditions, this iron-catalyzed aerobic oxidation process proceeds to synthesize functionalized and structurally diverse aromatic, aliphatic and heterocyclic nitriles. Addnl., applying this iron-based protocol, primary amides have also been prepared in a water medium. In the experiment, the researchers used many compounds, for example, 5-Bromo-3-cyanoindole (cas: 90271-86-6Recommanded Product: 5-Bromo-3-cyanoindole).

Cui, Yi et al. published their research in New Journal of Chemistry in 2008 | CAS: 85696-95-3

1-Methyl-1H-indol-4-amine (cas: 85696-95-3) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. 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). Formula: C9H10N2

The effect of substitution on the utility of piperidines and octahydroindoles for reversible hydrogen storage was written by Cui, Yi;Kwok, Samantha;Bucholtz, Andrew;Davis, Boyd;Whitney, Ralph A.;Jessop, Philip G.. And the article was included in New Journal of Chemistry in 2008.Formula: C9H10N2 This article mentions the following:

Substituted piperidines and octahydroindoles are compared in terms of their usability as reversible organic hydrogen storage liquids for hydrogen-powered fuel cells. Theor. Gaussian calculations indicate which structural features probably lower the enthalpy of dehydrogenation. Exptl. results show that attaching electron donating or conjugated substituents to the piperidine ring greatly increases the rate of catalytic dehydrogenation, with the greatest rates being observed with 4-aminopiperidine and piperidine-4-carboxamide. Undesired side reactions were observed with some compounds such as alkyl transfer reactions during the dehydrogenation of 4-dimethylaminopiperidine, C-O and C-N cleavage reactions during hydrogenation and/or subsequent dehydrogenation of 4-alkoxy- and 4-aminoindoles, and disproportionation during the hydrogenation of 4-aminopyridine. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-indol-4-amine (cas: 85696-95-3Formula: C9H10N2).

Zhao, Yin et al. published their research in Synlett in 2022 | 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Application In Synthesis of 5-Chloroindole-3-carboxaldehyde

Visible-Light-Promoted Indole C-3 Formylation Using Eosin Y as a Photoredox Catalyst was written by Zhao, Yin;Li, Hongfang;Yin, Shan;Wu, Yandan;Ni, Guanghui. And the article was included in Synlett in 2022.Application In Synthesis of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

A visible-light-mediated C-3 formylation of indole catalyzed by eosin Y has been developed using tetramethylethylenediamine as a carbon source and air as an oxidant. This protocol shows high tolerance to a large quantity of functional groups under mild conditions and provides 3-formylated indoles with good yields. This method is a highly attractive alternative to the approach of traditional formylation. 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).