January 2023 - Page 4 of 26 - Indole Building Blocks

Carbonnel, Elodie et al. published their research in Chemical Communications (Cambridge, United Kingdom) in 2017 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Quality Control of 2-(Phenylthio)isoindoline-1,3-dione

¹⁸F-Fluoroform: a ¹⁸F-trifluoromethylating agent for the synthesis of SCF₂¹⁸F-aromatic derivatives was written by Carbonnel, Elodie;Besset, Tatiana;Poisson, Thomas;Labar, Daniel;Pannecoucke, Xavier;Jubault, Philippe. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2017.Quality Control of 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:

The synthesis of various SCF₂¹⁸F-containing derivatives was reported by a transition metal-free process. By using HCF₂¹⁸F, readily generated from a bench-stable difluoromethyl sulfonium salt, various aromatic disulfides were easily converted into the desired radiolabeled trifluoromethylthiolated compounds in the presence of a base. This process was also extended to the corresponding selenium derivative In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Quality Control of 2-(Phenylthio)isoindoline-1,3-dione).

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

Bruynes, Cornelis A. et al. published their research in Journal of Organic Chemistry in 1982 | CAS: 24407-32-7

4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Synthetic Route of C8HBr4NO2

Catalysts for silylations with 1,1,1,3,3,3-hexamethyldisilazane was written by Bruynes, Cornelis A.;Jurriens, Theodorus K.. And the article was included in Journal of Organic Chemistry in 1982.Synthetic Route of C8HBr4NO2 This article mentions the following:

Saccharin, Na saccharin, 4-MeC₆H₄SO₂NHP(O)(OC₆H₄NO₂-4)₂, [PhOP(O)]₂NH, Cl₃CCONHP(O)(OC₆H₄NO₂-4)₂, etc. are effective catalysts for silylation with Me₃SiNHSiMe₃. Thus, treating BzOH with Me₃SiNHSiMe₃ in the presence of saccharin gave 92% BzOSiMe₃. In the experiment, the researchers used many compounds, for example, 4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7Synthetic Route of C8HBr4NO2).

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).

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).

Bookser, Brett C. et al. published their research in Journal of Combinatorial Chemistry in 2001 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. 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-Phenylisoindolin-1-one

Solid Phase Extraction Purification of Carboxylic Acid Products from 96-Well Format Solution Phase Synthesis with DOWEX 1μe8-400 Formate Anion Exchange Resin was written by Bookser, Brett C.;Zhu, Shirong. And the article was included in Journal of Combinatorial Chemistry in 2001.Name: 2-Phenylisoindolin-1-one This article mentions the following:

The anion exchange resin DOWEX 1×8-400 formate has been developed for the isolation or resin capture of carboxylic acids from solution phase reactions in a 96-well format using a batchwise solid phase extraction technique. Eleven different anion exchange resins (formate forms) were evaluated for their efficiency at scavenging aryl and aliphatic carboxylic acids from solution The model carboxylic acids had pK_as ranging from 3.40 to 4.89. Exchange efficiency onto the resin was pK_a dependent with the carboxylic acids but not with their diisopropylethylammonium salts. Exchange off of the resin also showed pK_a dependence with the stronger acids requiring more concentrated solvent acid for exchange. DOWEX 1×8-400 formate was determined to have superior capacity and the fastest exchange rate. Solvents suitable for exchanging the acids onto the resin were CH₂Cl₂, methanol, and various solvent/water mixtures Solvents suitable for exchanging the carboxylic acids off of the resin were TFA/solvent or HCO₂H/solvent mixtures The resin was found to swell best in CH₂Cl₂ and in polar protic solvents such as water, alcs., and acids. Application of this technique to the crude product mixtures from an arrayed reductive amination and an arrayed Stille reaction provided product carboxylic acids in yields averaging 57% and purities averaging 89%. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Name: 2-Phenylisoindolin-1-one).

Bai, Ya et al. published their research in Organic Letters in 2021 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. 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 2-Phenylisoindolin-1-one

Electroselective and Controlled Reduction of Cyclic Imides to Hydroxylactams and Lactams was written by Bai, Ya;Shi, Lingling;Zheng, Lianyou;Ning, Shulin;Che, Xin;Zhang, Zhuoqi;Xiang, Jinbao. And the article was included in Organic Letters in 2021.Application In Synthesis of 2-Phenylisoindolin-1-one This article mentions the following:

An efficient and practical electrochem. method for selective reduction of cyclic imides has been developed using a simple undivided cell with carbon electrodes at room temperature The reaction provides a useful strategy for the rapid synthesis of hydroxylactams and lactams in a controllable manner, which is tuned by elec. current and reaction time, and exhibits broad substrate scope and high functional group tolerance even to reduction-sensitive moieties. Initial mechanistic studies suggest that the approach heavily relies on the utilization of amines (e.g., i-Pr₂NH), which are able to generate α-aminoalkyl radicals. This protocol provides an efficient route for the cleavage of C-O bonds under mild conditions with high chemoselectivity. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Application In Synthesis of 2-Phenylisoindolin-1-one).

Zhang, Yu-Chen et al. published their research in Angewandte Chemie, International Edition in 2014 | CAS: 4583-55-5

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) 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). Recommanded Product: 5-Bromo-2,3-dimethyl-1H-indole

Organocatalytic Asymmetric Arylative Dearomatization of 2,3-Disubstituted Indoles Enabled by Tandem Reactions was written by Zhang, Yu-Chen;Zhao, Jia-Jia;Jiang, Fei;Sun, Si-Bing;Shi, Feng. And the article was included in Angewandte Chemie, International Edition in 2014.Recommanded Product: 5-Bromo-2,3-dimethyl-1H-indole This article mentions the following:

The organocatalytic asym. arylative dearomatization of indoles was achieved through two tandem approaches involving 2,3-disubstituted indoles and quinone imine ketals. One approach utilized the enantioselective cascade 1,4 addition/alc. elimination reaction, the other employed the one-pot tandem arylative dearomatization/transfer hydrogenation sequence. In both cases, enantiomerically pure indole derivatives I [R¹ = H, 4-Me, 5-Me, etc; R² = Me, Et; R³ = Me, Et; R = Me, Et, Pr-i, Bu; PG = Boc, Cbz] and II [R¹ = H, 4-Me, 5-Me, etc; R² = Me, Et; R³ = Me, Et; R = Me, Et, Pr-i, Bu; PG = Boc, Cbz] that bear an all-carbon quaternary stereogenic center were generated in high yields and excellent stereoselectivities (all d.r.>95:5, up to 99 % ee). In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Recommanded Product: 5-Bromo-2,3-dimethyl-1H-indole).