10/02/2023 - Page 11 of 13 - Indole Building Blocks

Khaledi, Hamid et al. published their research in Archiv der Pharmazie (Weinheim, Germany) in 2011 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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.Application of 827-01-0

Antioxidant, Cytotoxic Activities, and Structure-Activity Relationship of Gallic Acid-based Indole Derivatives was written by Khaledi, Hamid;Alhadi, Abeer A.;Yehye, Wagee A.;Ali, Hapipah Mohd.;Abdulla, Mahmood A.;Hassandarvish, Pouya. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2011.Application of 827-01-0 This article mentions the following:

A new series of gallic hydrazones containing an indole moiety was synthesized through the reaction of gallic hydrazide and different indole carboxaldehydes. Their antioxidant activities were determined on DPPH radical scavenging and inhibition of lipid peroxidation The in-vitro cytotoxic activities of the compounds were evaluated against HCT-116 (human colon cancer cell line) and MCF-7 (estrogen-dependent human breast cancer cell line) by the MTT method. An attempt to correlate the biol. results with their structural characteristics has been done. A limited pos. structure activity relationship was found between cytotoxic and antioxidant activities. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Application of 827-01-0).

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

Jung, So Hyun et al. published their research in Asian Journal of Organic Chemistry in 2019 | 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.SDS of cas: 14204-27-4

Enantioselective Synthesis of Chiral 伪-Alkylthiomalonates via a Phase-Transfer-Catalyzed 伪-Sulfenylation of 伪-Alkylmalonates was written by Jung, So Hyun;Kim, Byungsoo;Park, Cheonhyoung;Kim, Jeongseok;Ha, Min Woo;Hong, Suckchang;Park, Hyeung-geun. And the article was included in Asian Journal of Organic Chemistry in 2019.SDS of cas: 14204-27-4 This article mentions the following:

A synthetic method for accessing chiral 伪-alkylthio-伪-alkylmalonates I (R = allyl, i-Pr, C₆H₅, etc.) was successfully established. The enantioselective 伪-sulfenylation of 伪-alkylmalonates via phase-transfer catalysis [N-alkylthiophthalimide, 50% aqueous KOH, toluene, -40掳 and N-2′,3′,4′-trifluorophenyl-dihydroquinidium bromide] provided the corresponding 伪-alkylthio-伪-alkylmalonates in high chem. yields (up to 97%) and optical purities (up to 90% ee). In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4SDS of cas: 14204-27-4).

Bujok, Robert et al. published their research in Synlett in 2012 | CAS: 3484-23-9

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

Expedient synthesis of 1-hydroxy-4- and 1-hydroxy-6-nitroindoles was written by Bujok, Robert;Wrobel, Zbigniew;Wojciechowski, Krzysztof. And the article was included in Synlett in 2012.HPLC of Formula: 3484-23-9 This article mentions the following:

Reaction of 伪-chloroalkyl ketones with 1,3-dinitrobenzenes provided 2,4-dinitrobenzyl ketones, which on reduction with SnCl₂ gave 6-nitro derivatives of 1-hydroxyindoles. An alternative approach is the condensation of 2,4- and 2,6-dinitrotoluenes with (CO₂Et)₂ or F₃CCO₂Et to yield dinitrobenzyl ketones, which on reduction with SnCl₂ afforded nitro derivatives of 1-hydroxyindol-2-carboxylates or 1-hydroxy-2-(trifluoromethyl)indoles, resp. In the experiment, the researchers used many compounds, for example, 2-Methyl-6-nitro-1H-indole (cas: 3484-23-9HPLC of Formula: 3484-23-9).

Jiang, Huanfeng et al. published their research in Journal of Organic Chemistry in 2017 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Computed Properties of C8H6N2O2

Copper-Catalyzed Aerobic Oxidative Regioselective Thiocyanation of Aromatics and Heteroaromatics was written by Jiang, Huanfeng;Yu, Wentao;Tang, Xiaodong;Li, Jianxiao;Wu, Wanqing. And the article was included in Journal of Organic Chemistry in 2017.Computed Properties of C8H6N2O2 This article mentions the following:

A copper-catalyzed aerobic oxidative reaction between aromatics or heteroaromatics with KSCN is developed by using O₂ as the oxidant. The combination of Cu(OTf)₂, N,N,N’,N’-tetramethylethylenediamine (TMEDA) and BF₃路Et₂O provides an efficient catalytic system, affording substituted thiocyanation products and 2-aminobenzothiazoles in excellent yields. The reaction also possesses a good functional group tolerance for both strong electron-withdrawing and electron-donating groups. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Computed Properties of C8H6N2O2).

Clavadetscher, Jessica et al. published their research in Angewandte Chemie, International Edition in 2017 | CAS: 754214-56-7

7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.SDS of cas: 754214-56-7

In-cell dual drug synthesis by cancer-targeting palladium catalysts was written by Clavadetscher, Jessica;Indrigo, Eugenio;Chankeshwara, Sunay V.;Lilienkampf, Annamaria;Bradley, Mark. And the article was included in Angewandte Chemie, International Edition in 2017.SDS of cas: 754214-56-7 This article mentions the following:

Transition metals have been successfully applied to catalyze non-natural chem. transformations within living cells, with the highly efficient labeling of subcellular components and the activation of prodrugs. In vivo applications, however, have been scarce, with a need for the specific cellular targeting of the active transition metals. Here, we show the design and application of cancer-targeting palladium catalysts, with their specific uptake in brain cancer (glioblastoma) cells, while maintaining their catalytic activity. In these cells, for the first time, two different anticancer agents were synthesized simultaneously intracellularly, by two totally different mechanisms (in situ synthesis and decaging), enhancing the therapeutic effect of the drugs. Tumor specificity of the catalysts together with their ability to perform simultaneous multiple bioorthogonal transformations will empower the application of in vivo transition metals for drug activation strategies. In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7SDS of cas: 754214-56-7).

Cheng, Cheng et al. published their research in Tetrahedron in 2015 | CAS: 3484-23-9

2-Methyl-6-nitro-1H-indole (cas: 3484-23-9) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. 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.HPLC of Formula: 3484-23-9

One-pot three-component reactions of methyl ketones, phenols and a nucleophile: an expedient way to synthesize densely substituted benzofurans was written by Cheng, Cheng;Liu, Changhui;Gu, Yanlong. And the article was included in Tetrahedron in 2015.HPLC of Formula: 3484-23-9 This article mentions the following:

Three-component reactions of glyoxals R¹C(O)CHO (R¹ = C₆H₅, 1-benzofuran-2-yl, cyclopropyl, etc.), sesamol/1,4-benzenediol/1,2,4-benzenetriol/phenol and indoles I (R² = H, CH₃, C₆H₅, CO₂CH₂CH₃; R³ = H, Et; R⁴ = H, 6-NO₂, 5-CH₃) were developed with the aid of acid-catalyst, which produced various densely substituted benzofurans e.g., II with good to excellent yields. On the basis of this observation, a one-pot, step-wise reaction was developed by using Me ketones R⁵C(O)CH₃ (R⁵ = t-Bu, Ph, fluoren-2-yl, thiophen-2-yl, etc.) instead of using glyoxal component in I₂/DMSO system. The indole component can be replaced by some other nucleophiles, such as 1,2,4-trimethoxybenzene and thiophenol. In the experiment, the researchers used many compounds, for example, 2-Methyl-6-nitro-1H-indole (cas: 3484-23-9HPLC of Formula: 3484-23-9).

Yuan, Yu-Chao et al. published their research in Catalysis Science & Technology in 2019 | 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Recommanded Product: 5388-42-1

Site-selective Ru-catalyzed C-H bond alkenylation with biologically relevant isoindolinones: a case of catalyst performance controlled by subtle stereo-electronic effects of the weak directing group was written by Yuan, Yu-Chao;Bruneau, Christian;Roisnel, Thierry;Gramage-Doria, Rafael. And the article was included in Catalysis Science & Technology in 2019.Recommanded Product: 5388-42-1 This article mentions the following:

Alkenylated isoindolinones I [R = CO₂Me, Ph, 4-FC₆H₄, etc.; R¹ = H; R² = H, Me, Cl, MeO, CN, CO₂Et; R³ = R⁴ = H, Me, MeO; R¹R² = OCH₂O] were prepared via site-selective Ru-catalyzed C-H bond alkenylation of isoindolinones with alkenes. Notably, besides the presence of two aromatic C-H sites available for functionalization, selective mono-alkenylation in the ortho-position with respect to the nitrogen atom were achieved with a readily available ruthenium catalyst. The scalability, versatility and high functional group tolerance of the catalysis enabled the late-stage functionalization of biol. relevant indoprofen and further derivatizations. Preliminary mechanistic studies indicated, the ease of the C-H bond activation step, the key role of the carbonyl group as a weak directing group throughout the catalytic cycle and the unexpected subtle differences associated between cyclic amides and imides as weak directing groups in ruthenium-catalyzed C-H bond alkenylation reactions. The isolation and role of an unprecedented off-cycle ruthenium complex was discussed as well. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Recommanded Product: 5388-42-1).

Fukuda, Yasuhiro et al. published their research in Chemical Science in 2021 | 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. 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.Category: indole-building-block

Peptoid-based reprogrammable template for cell-permeable inhibitors of protein-protein interactions was written by Fukuda, Yasuhiro;Yokomine, Marin;Kuroda, Daisuke;Tsumoto, Kouhei;Morimoto, Jumpei;Sando, Shinsuke. And the article was included in Chemical Science in 2021.Category: indole-building-block This article mentions the following:

The development of inhibitors of intracellular protein-protein interactions (PPIs) is of great significance for drug discovery, but the generation of a cell-permeable mol. with high affinity to protein is challenging. Oligo(N-substituted glycines) (oligo-NSGs), referred to as peptoids, are attractive as potential intracellular PPI inhibitors owing to their high membrane permeability. However, their intrinsically flexible backbones make the rational design of inhibitors difficult. Here, we propose a peptoid-based rational approach to develop cell-permeable PPI inhibitors using oligo(N-substituted alanines) (oligo-NSAs). The rigid structures of oligo-NSAs enable independent optimization of each N-substituent to improve binding affinity and membrane permeability, while preserving the backbone shape. A mol. with optimized N-substituents inhibited a target PPI in cells, which demonstrated the utility of oligo-NSA as a reprogrammable template to develop intracellular PPI inhibitors. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Category: indole-building-block).

Lin, Hui-Shan et al. published their research in Chemical Communications (Cambridge, United Kingdom) in 2022 | CAS: 170489-16-4

1,4-Dimethyl-1H-indole-3-carbaldehyde (cas: 170489-16-4) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.SDS of cas: 170489-16-4

Electrosynthesis of (hetero)aryl nitriles from 伪-imino-oxy acids via oxidative decarboxylation/N-O cleavage was written by Lin, Hui-Shan;Chen, Shu-Jun;Huang, Jing-Mei. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2022.SDS of cas: 170489-16-4 This article mentions the following:

A new method for the synthesis of (hetero)aryl nitriles via iminyl radicals was developed through the electrochem. oxidative decarboxylation of 伪-imino-oxy acids. This protocol provides an efficient approach to nitriles with a broad range of functional-group tolerance under ambient conditions and can be applied for one-pot gram-scale synthesis. In the experiment, the researchers used many compounds, for example, 1,4-Dimethyl-1H-indole-3-carbaldehyde (cas: 170489-16-4SDS of cas: 170489-16-4).

Kametani, Tetsuji et al. published their research in Journal of Heterocyclic Chemistry in 1978 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Name: 2-Phenylisoindolin-1-one

Studies on the syntheses of heterocyclic compounds. Part 742. Studies on the syntheses of analgesics. Part 50. Synthesis of optically active 2-[4-(1-oxo-2-isoindolinyl)phenyl]propanoic acid was written by Kametani, Tetsuji;Kigasawa, Kazuo;Hiiragi, Mineharu;Ishimaru, Haruhide;Haga, Seiji;Shirayama, Keiko. And the article was included in Journal of Heterocyclic Chemistry in 1978.Name: 2-Phenylisoindolin-1-one This article mentions the following:

Analgesic and antiinflammatory I (R = CHMeCO₂H), prepared from I (R = COMe) (II) via oxidation of I (R = CHMeCOCO₂H) (III) or hydrolysis of I (R = Q, R¹ = H, R² = CH), was resolved via diastereoisomeric salts with cinchonidine. III was obtained from II in 5 steps via I [R = CMe:C(CN)CO₂Et; Q, where R¹ = CO₂NH₂, R² = CO₂Et and R¹ = CONH₂, R² = CO₂Na; R = COCONH₂] or by Darzens reaction of II with ClCH₂CO₂Et and treatment of the resulting I (R = Q, R¹ = H, R² = CO₂Et) with concentrated HCl and HOAc. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Name: 2-Phenylisoindolin-1-one).