162.15 | - Indole Building Blocks

Dong, Yuan-Qing et al. published their research in ACS Catalysis in 2022 | CAS: 4769-97-5

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

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).

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

Liang, Yuwang et al. published their research in New Journal of Chemistry in 2022 | CAS: 4769-97-5

4-Nitroindole (cas: 4769-97-5) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Application In Synthesis of 4-Nitroindole

In situ preparation of a ferric polymeric aluminum chloride-silica gel nanocatalyst by mechanical grinding and its solid-phase catalytic behavior in organic synthesis was written by Liang, Yuwang;Wang, Gang;Li, Xiang;Zhang, Qiuping;Zhan, Haijuan;Bi, Shuxian;Wu, Zhiqiang;Liu, Wanyi. And the article was included in New Journal of Chemistry in 2022.Application In Synthesis of 4-Nitroindole This article mentions the following:

In recent years, clean and sustainable mechanochem. solvent-free reactions have emerged as a viable alternative to solution chem. In order to completely solve the problem of environmental pollution caused by solvents and surfactants in LASC and LASSC systems, a green method for the in situ preparation of environmentally friendly inorganic polymeric Lewis acids and silica gel as nanocatalysts (PLASC) under solvent-free mech. grinding conditions was designed and realized by mechanochem. means, which is simple to operate and the process generates no other waste. Subsequently, 3-alkylindole derivatives (35-75%), 尾-amino alc. derivatives (90%), benzimidazole derivatives (85-90%) and quinoxaline derivatives (93-99%) were synthesized by a one-pot cooking method under continuous grinding conditions. The mechanism of in situ self-assembly of PAFC and silica gel on the silica gel surface under mech. forces and the new catalytically active species-Si-O-Al(Fe) polynuclear metal complexes resulting from chem. reforming were discovered and confirmed by SEM, HR-TEM, FT-IR, XRD and XPS tests as well as by solution morphol. studies. The true active center -O-Fe-O-Si-O-/-O-Si-O-Al-O- chem. bonding unit was revealed and found to be a nanoscale fibrous structure that is highly stable and can be reused at least 10 times without deactivation. The PLASC catalyst has remarkable green chem. properties such as easy recycling and a very low E factor, making it a new type of cheap, efficient and green catalyst. In the experiment, the researchers used many compounds, for example, 4-Nitroindole (cas: 4769-97-5Application In Synthesis of 4-Nitroindole).

Yanagita, Ryo C. et al. published their research in Journal of Medicinal Chemistry in 2008 | CAS: 4769-97-5

4-Nitroindole (cas: 4769-97-5) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.COA of Formula: C8H6N2O2

Synthesis, Conformational Analysis, and Biological Evaluation of 1-Hexylindolactam-V10 as a Selective Activator for Novel Protein Kinase C Isozymes was written by Yanagita, Ryo C.;Nakagawa, Yu;Yamanaka, Nobuhiro;Kashiwagi, Kaori;Saito, Naoaki;Irie, Kazuhiro. And the article was included in Journal of Medicinal Chemistry in 2008.COA of Formula: C8H6N2O2 This article mentions the following:

Conventional and novel protein kinase C (PKC) isoenzymes are the main targets of tumor promoters. We developed 1-hexylindolactam-V10 (I) as a selective activator for novel PKC isoenzymes that play important roles in various cellular processes related to tumor promotion, ischemia-reperfusion injury in the heart, and Alzheimer’s disease. The compound existed as a mixture of three conformers. The trans-amide restricted analogs of I hardly bound to PKC isoenzymes, suggesting that the active conformation of I could be that with a cis-amide. Compound I selectively translocated novel PKC isoenzymes over conventional PKC isoenzymes in HeLa cells at 0.1-1 渭M. These results suggest that I could be useful for the functional anal. of novel PKC isoenzymes. In the experiment, the researchers used many compounds, for example, 4-Nitroindole (cas: 4769-97-5COA of Formula: C8H6N2O2).

Han, Shuwen et al. published their research in Bioorganic Chemistry in 2022 | CAS: 4769-97-5

4-Nitroindole (cas: 4769-97-5) 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. 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). Category: indole-building-block

Structure-Based design of Marine-derived Meridianin C derivatives as glycogen synthase kinase 3尾 inhibitors with improved oral bioavailability: From aminopyrimidyl-indoles to the sulfonyl analogues was written by Han, Shuwen;Zhou, Wei;Zhuang, Chunlin;Chen, Fener. And the article was included in Bioorganic Chemistry in 2022.Category: indole-building-block This article mentions the following:

Glycogen synthase kinase 3尾 (GSK-3尾) has become an attractive target for the treatment of diabetes. Compound I is an indole-based GSK-3尾 inhibitor designed from the Meridianin C, a marine natural product (MNP) isolated from Aplidium聽meridianum. However, this compound has a moderate inhibitory activity toward GSK-3尾 (IC₅₀ = 24.4 渭M), moderate glucose uptake (38%), and especially, a low oral bioavailability (F = 11.4%). In the present study, applying the structure-based design strategy, a series of derivatives modified on the indole moiety were synthesized based on the lead compound I, followed by evaluating their cytotoxic activity, antihyperglycemic activity, and kinase inhibitory activity. Among this series, compound 6x with a sulfonyl group displayed the highest glucose uptake (83.5%) in muscle L6 cells, showing much higher inhibitory activity against GSK-3尾 (IC₅₀ = 5.25 渭M). Mol. docking indicated that compound 6x was properly inserted into the ATP-binding binding pocket of GSK-3尾 with a higher docking score (-8.145 kcal/mol) compared with that of compound I (-6.950 kcal/mol), interpreting the higher kinase inhibitory activity toward GSK-3尾. Remarkably, compound 6x showed favorable drug-like properties, including significantly better oral bioavailability (F = 47.4%) and no two-week acute toxicity at a dose of 1g/kg. Our findings suggest that these MNP-derived sulfonyl indole derivatives could be used as lead compounds for the development of anti-hyperglycemic drugs. In the experiment, the researchers used many compounds, for example, 4-Nitroindole (cas: 4769-97-5Category: indole-building-block).

4-Nitroindole (cas: 4769-97-5) 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. 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). Category: indole-building-block

Tanaka, Minoru et al. published their research in Tetrahedron in 2011 | CAS: 4769-97-5

4-Nitroindole (cas: 4769-97-5) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Category: indole-building-block

Convenient synthesis of chiral tryptophan derivatives using Negishi cross-coupling was written by Tanaka, Minoru;Hikawa, Hidemasa;Yokoyama, Yuusaku. And the article was included in Tetrahedron in 2011.Category: indole-building-block This article mentions the following:

A facile synthetic procedure for chiral tryptophan derivatives using Negishi cross-coupling reaction of serine-derived iodoalanine with 3-haloindole is described. The best result was obtained when the reaction of N-tosyl-3-bromoindole with N-Cbz-iodoalanine Me ester (Cbz = benzyloxycarbonyl) was carried out by the combination of Pd₂(dba)₃ and sterically hindered ferrocenyl ligand Q-PHOS. This reaction condition not only gave the desired tryptophan derivative as high as 76% yield, but also suppressed the formation of undesired products, the dehalogenated indole and the homodimer of indole, which were difficult to sep. This reaction was extended to the synthesis of various tryptophan derivatives having substituents on the benzene ring. The characteristic of this reaction is the practical biomimetic synthesis of chiral tryptophan derivatives in one-step. In the experiment, the researchers used many compounds, for example, 4-Nitroindole (cas: 4769-97-5Category: indole-building-block).

Kikkawa, Shoko et al. published their research in Crystal Growth & Design in 2021 | CAS: 4769-97-5

4-Nitroindole (cas: 4769-97-5) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Product Details of 4769-97-5

High Proportion of Chiral Crystallization of Achiral Indolyl Sulfonamides: Effect of Intermolecular Interactions was written by Kikkawa, Shoko;Maeno, Isae;Katagiri, Kosuke;Murayama, Yuta;Nozawa, Mariko;Hikawa, Hidemasa;Azumaya, Isao. And the article was included in Crystal Growth & Design in 2021.Product Details of 4769-97-5 This article mentions the following:

We investigated the effect of indole moieties on chiral crystallization In this regard, we assessed the influence of intermol. interactions and contacts on the assembly of these mols. A systematic anal. of 62 crystal structures of secondary aromatic sulfonamides bearing 4-, 5-, 6-, and 7-aminoindolyl groups revealed that the proportion of indolyl compounds showing chiral crystallization was apparently higher (21%, except for crypto-racemate) than that of nonindolyl sulfonamides (11%). Moreover, 33% (5 out of 15 crystals) and 44% (7 out of 16 crystals) of 4- and 7-indolyl sulfonamide derivatives preferred chiral crystallization, resp. This suggested a correlation between the type of contact and the chirality of the assembly of adjacent mols. Specifically, the proportion of achiral indolyl sulfonamides undergoing chiral crystallization was drastically increased by N(indole)H路路路O interactions, slightly increased by C(sp²)H路路路蟺 interactions, and decreased owing to 蟺路路路蟺 interactions. These tendencies were also true for sulfonamides with different substituents, which suggested that the T-shape contact would be more favorable than 蟺路路路蟺 interactions for chiral crystallization In the experiment, the researchers used many compounds, for example, 4-Nitroindole (cas: 4769-97-5Product Details of 4769-97-5).

Han, Shuwen et al. published their research in Bioorganic Chemistry in 2022 | CAS: 4769-97-5

4-Nitroindole (cas: 4769-97-5) 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. 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). Category: indole-building-block

Structure-Based design of Marine-derived Meridianin C derivatives as glycogen synthase kinase 3β inhibitors with improved oral bioavailability: From aminopyrimidyl-indoles to the sulfonyl analogues was written by Han, Shuwen;Zhou, Wei;Zhuang, Chunlin;Chen, Fener. And the article was included in Bioorganic Chemistry in 2022.Category: indole-building-block This article mentions the following:

Glycogen synthase kinase 3β (GSK-3β) has become an attractive target for the treatment of diabetes. Compound I is an indole-based GSK-3β inhibitor designed from the Meridianin C, a marine natural product (MNP) isolated from Aplidium meridianum. However, this compound has a moderate inhibitory activity toward GSK-3β (IC₅₀ = 24.4 μM), moderate glucose uptake (38%), and especially, a low oral bioavailability (F = 11.4%). In the present study, applying the structure-based design strategy, a series of derivatives modified on the indole moiety were synthesized based on the lead compound I, followed by evaluating their cytotoxic activity, antihyperglycemic activity, and kinase inhibitory activity. Among this series, compound 6x with a sulfonyl group displayed the highest glucose uptake (83.5%) in muscle L6 cells, showing much higher inhibitory activity against GSK-3β (IC₅₀ = 5.25 μM). Mol. docking indicated that compound 6x was properly inserted into the ATP-binding binding pocket of GSK-3β with a higher docking score (-8.145 kcal/mol) compared with that of compound I (-6.950 kcal/mol), interpreting the higher kinase inhibitory activity toward GSK-3β. Remarkably, compound 6x showed favorable drug-like properties, including significantly better oral bioavailability (F = 47.4%) and no two-week acute toxicity at a dose of 1g/kg. Our findings suggest that these MNP-derived sulfonyl indole derivatives could be used as lead compounds for the development of anti-hyperglycemic drugs. In the experiment, the researchers used many compounds, for example, 4-Nitroindole (cas: 4769-97-5Category: indole-building-block).

4-Nitroindole (cas: 4769-97-5) 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. 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). Category: indole-building-block

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

Tanaka, Minoru et al. published their research in Tetrahedron in 2011 | CAS: 4769-97-5

Kikkawa, Shoko et al. published their research in Crystal Growth & Design in 2021 | CAS: 4769-97-5

We investigated the effect of indole moieties on chiral crystallization In this regard, we assessed the influence of intermol. interactions and contacts on the assembly of these mols. A systematic anal. of 62 crystal structures of secondary aromatic sulfonamides bearing 4-, 5-, 6-, and 7-aminoindolyl groups revealed that the proportion of indolyl compounds showing chiral crystallization was apparently higher (21%, except for crypto-racemate) than that of nonindolyl sulfonamides (11%). Moreover, 33% (5 out of 15 crystals) and 44% (7 out of 16 crystals) of 4- and 7-indolyl sulfonamide derivatives preferred chiral crystallization, resp. This suggested a correlation between the type of contact and the chirality of the assembly of adjacent mols. Specifically, the proportion of achiral indolyl sulfonamides undergoing chiral crystallization was drastically increased by N(indole)H···O interactions, slightly increased by C(sp²)H···π interactions, and decreased owing to π···π interactions. These tendencies were also true for sulfonamides with different substituents, which suggested that the T-shape contact would be more favorable than π···π interactions for chiral crystallization In the experiment, the researchers used many compounds, for example, 4-Nitroindole (cas: 4769-97-5Product Details of 4769-97-5).

Kikkawa, Shoko et al. published their research in Crystal Growth & Design in 2021 | CAS: 4769-97-5

We investigated the effect of indole moieties on chiral crystallization In this regard, we assessed the influence of intermol. interactions and contacts on the assembly of these mols. A systematic anal. of 62 crystal structures of secondary aromatic sulfonamides bearing 4-, 5-, 6-, and 7-aminoindolyl groups revealed that the proportion of indolyl compounds showing chiral crystallization was apparently higher (21%, except for crypto-racemate) than that of nonindolyl sulfonamides (11%). Moreover, 33% (5 out of 15 crystals) and 44% (7 out of 16 crystals) of 4- and 7-indolyl sulfonamide derivatives preferred chiral crystallization, resp. This suggested a correlation between the type of contact and the chirality of the assembly of adjacent mols. Specifically, the proportion of achiral indolyl sulfonamides undergoing chiral crystallization was drastically increased by N(indole)H···O interactions, slightly increased by C(sp²)H···π interactions, and decreased owing to π···π interactions. These tendencies were also true for sulfonamides with different substituents, which suggested that the T-shape contact would be more favorable than π···π interactions for chiral crystallization In the experiment, the researchers used many compounds, for example, 4-Nitroindole (cas: 4769-97-5Product Details of 4769-97-5).