06/01/2023 - Page 3 of 3 - Indole Building Blocks

Qin, Hong et al. published their research in Journal of Organic Chemistry in 2022 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Electric Literature of C8H6N2O2

Regioselective C3-Fluoroalcoholation of Indoles with Heptafluoroisopropyl Iodide via Palladium-Catalyzed C(sp²)-C(sp³) Cross-Coupling in the Presence of O₂ was written by Qin, Hong;Zhang, Zhen;Qiao, Kai;Chen, Xinran;He, Wei;Liu, Chengkou;Yang, Xiaobing;Yang, Zhao;Fang, Zheng;Guo, Kai. And the article was included in Journal of Organic Chemistry in 2022.Electric Literature of C8H6N2O2 This article mentions the following:

An efficient method for C3-fluoroalcoholation of indole derivatives was developed by merging C-F cleavage and C-C bond coupling, using free (NH)-indoles and heptafluoroisopropyl iodides as precursors. Preliminary mechanistic studies indicate that the bimetallic co-mediated C-F bond cleavage and the trifluoroacetate moiety play an essential role. Notably, this strategy constructs derivatizations through the modifiable carbon-oxygen bond. A broad range of structurally valuable organofluorine products was obtained, which shows excellent functional group tolerance. Furthermore, easily accessible materials were utilized and circumvented two troublesome steps of installing and removing an external auxiliary. This was the first report to introduce 3-fluoroalcoholated indoles via fluorohalides. This reaction offers a straightforward and efficient platform to access worthwhile fluorinated free (NH)-heteroarenes derivatives In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Electric Literature of C8H6N2O2).

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

Damgaard, Maria et al. published their research in ACS Chemical Neuroscience in 2015 | CAS: 150560-58-0

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Safety of 5-Isopropylindoline-2,3-dione

Identification of the First Highly Subtype-Selective Inhibitor of Human GABA Transporter GAT3 was written by Damgaard, Maria;Al-Khawaja, Anas;Vogensen, Stine B.;Jurik, Andreas;Sijm, Maarten;Lie, Maria E. K.;Baek, Mathias I.;Rosenthal, Emil;Jensen, Anders A.;Ecker, Gerhard F.;Froelund, Bente;Wellendorph, Petrine;Clausen, Rasmus P.. And the article was included in ACS Chemical Neuroscience in 2015.Safety of 5-Isopropylindoline-2,3-dione This article mentions the following:

Screening a library of small-mol. compounds using a cell line expressing human GABA transporter 3 (hGAT3) in a [³H]GABA uptake assay identified isatin derivatives as a new class of hGAT3 inhibitors. A subsequent structure-activity relationship (SAR) study led to the identification of hGAT3-selective inhibitors (i.e., compounds 20 and 34) that were superior to the reference hGAT3 inhibitor, (S)-SNAP-5114, in terms of potency (low micromolar IC₅₀ values) and selectivity (>30-fold selective for hGAT3 over hGAT1/hGAT2/hBGT1). Further pharmacol. characterization of compound 20 (5-(thiophen-2-yl)indoline-2,3-dione) revealed a noncompetitive mode of inhibition at hGAT3. This suggests that this compound class, which has no structural resemblance to GABA, has a binding site different from the substrate, GABA. This was supported by a mol. modeling study that suggested a unique binding site that matched the observed selectivity, inhibition kinetics, and SAR of the compound series. These compounds are the most potent GAT3 inhibitors reported to date that provide selectivity for GAT3 over other GABA transporter subtypes. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Safety of 5-Isopropylindoline-2,3-dione).

Gritsch, Philipp J. et al. published their research in Organic Letters in 2013 | 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Quality Control of 5-Chloroindole-3-carboxaldehyde

Enantioselective Synthesis of Cyclohepta[b]indoles: Gram-Scale Synthesis of (S)-SIRT1-Inhibitor IV was written by Gritsch, Philipp J.;Stempel, Erik;Gaich, Tanja. And the article was included in Organic Letters in 2013.Quality Control of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

An enantioselective gram-scale synthesis of one of the most potent SIRT1-inhibitors, I, has been accomplished by an unprecedented domino reaction Wittig reaction/divinylcyclopropane rearrangement sequence establishing the cyclohepta[b]indole core. This method was developed for application in natural product synthesis of a variety of indole alkaloids. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Quality Control of 5-Chloroindole-3-carboxaldehyde).

Kost, A. N. et al. published their research in Khimiya Geterotsiklicheskikh Soedinenii in 1981 | CAS: 16732-64-2

4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2) 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). Related Products of 16732-64-2

Reaction of indoles with trifluoroacetic acid was written by Kost, A. N.;Budylin, V. A.;Romanova, N. N.;Matveeva, E. D.. And the article was included in Khimiya Geterotsiklicheskikh Soedinenii in 1981.Related Products of 16732-64-2 This article mentions the following:

Trifluoroacetylindoles I (R = H, 4-Me, 6-Br, 7-Ph) are obtained in 10, 27, 12, and 3% yields, resp., when the corresponding indole-2-carboxylic acids are heated with F₃CCO₂H 13-26 h on a boiling water bath. In the experiment, the researchers used many compounds, for example, 4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2Related Products of 16732-64-2).

Wen, Jialin et al. published their research in Organic Letters in 2018 | CAS: 3484-23-9

2-Methyl-6-nitro-1H-indole (cas: 3484-23-9) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Safety of 2-Methyl-6-nitro-1H-indole

Bronsted-Acid-Promoted Rh-Catalyzed Asymmetric Hydrogenation of N-Unprotected Indoles: A Cocatalysis of Transition Metal and Anion Binding was written by Wen, Jialin;Fan, Xiangru;Tan, Renchang;Chien, Hui-Chun;Zhou, Qinghai;Chung, Lung Wa;Zhang, Xumu. And the article was included in Organic Letters in 2018.Safety of 2-Methyl-6-nitro-1H-indole This article mentions the following:

In the presence of [Rh(cod)Cl]₂, the thiourea-substituted ferrocenyldiphosphine ZhaoPhos, and HCl in AcOH, 2-alkyl- and 2,3-dialkyl-substituted N-unprotected indoles underwent diastereoselective and enantioselective hydrogenation to yield nonracemic indolines such as (S)-2-methylindoline and (S,S)-2,3-dimethylindoline in 48-99% yields and 82-98% ee; hydrogenation of 6-nitro-2-methylindole and 2-phenylindole gave products in low or no yield. DFT calculations of the relative free energies of transition states and intermediates in the hydrogenation of 2-methylindole support an outer-sphere mechanism for the hydrogenation; complexation of ZhaoPhos with chloride and DFT calculations indicate that anion binding is an important secondary interaction in catalysis. In the experiment, the researchers used many compounds, for example, 2-Methyl-6-nitro-1H-indole (cas: 3484-23-9Safety of 2-Methyl-6-nitro-1H-indole).