Tag: 100-200

Ultraviolet spectra of indoles in strong sulfuric acid was written by Mollan, R. C.;Harmey, M. A.;Donnelly, D. M. X.. And the article was included in Phytochemistry (Elsevier) in 1973.SDS of cas: 6639-06-1 This article mentions the following:

Measurement of the uv spectra in 12.7M H2SO4 at 30 and 70° provides a simple, quant. and specific method for the identification of variously substituted, naturally occurring plant indoles in μg quantities. In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1SDS of cas: 6639-06-1).

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

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

Probing the Subpockets of Factor Xa Reveals Two Binding Modes for Inhibitors Based on a 2-Carboxyindole Scaffold: A Study Combining Structure-Activity Relationship and X-ray Crystallography was written by Nazare, Marc;Will, David W.;Matter, Hans;Schreuder, Herman;Ritter, Kurt;Urmann, Matthias;Essrich, Melanie;Bauer, Armin;Wagner, Michael;Czech, Joerg;Lorenz, Martin;Laux, Volker;Wehner, Volkmar. And the article was included in Journal of Medicinal Chemistry in 2005.Quality Control of Methyl 5-fluoro-1H-indole-2-carboxylate This article mentions the following:

Structure-activity relationships within a series of highly potent 2-carboxyindole-based factor Xa inhibitors incorporating a neutral P1 ligand are described with particular emphasis on the structural requirements for addressing subpockets of the factor Xa enzyme. Interactions with the subpockets were probed by systematic substitution of the 2-carboxyindole scaffold, in combination with privileged P1 and P4 substituents. Combining the most favorable substituents at the indole nucleus led to the discovery of a remarkably potent factor Xa inhibitor displaying a K_i value of 0.07 nM. X-ray crystallog. of inhibitors bound to factor Xa revealed substituent-dependent switching of the inhibitor binding mode and provided a rationale for the SAR obtained. These results underscore the key role played by the P1 ligand not only in determining the binding affinity of the inhibitor by direct interaction but also in modifying the binding mode of the whole scaffold, resulting in a nonlinear SAR. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Quality Control of Methyl 5-fluoro-1H-indole-2-carboxylate).

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) 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.Quality Control of Methyl 5-fluoro-1H-indole-2-carboxylate

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

The relation between position and chemical composition of bis-indole substituents determines their interactions with G-quadruplex DNA was written by Prasad, Bagineni;Das, Rabindra Nath;Jamroskovic, Jan;Kumar, Rajendra;Hedenstroem, Mattias;Sabouri, Nasim;Chorell, Erik. And the article was included in Chemistry – A European Journal in 2020.COA of Formula: C8H6N2O2 This article mentions the following:

G-quadruplex (G4) DNA structures are linked to fundamental biol. processes and human diseases, which has triggered the development of compounds that affect these DNA structures. However, more knowledge is needed about how small mols. interact with G4 DNA structures. This study describes the development of a new class of bis-indoles (3,3-diindolyl-Me derivatives) and detailed studies of how they interact with G4 DNA using orthogonal assays, biophys. techniques, and computational studies. This revealed compounds that strongly bind and stabilize G4 DNA structures, and detailed binding interactions which for example, show that charge variance can play a key role in G4 DNA binding. Furthermore, the structure-activity relationships generated opened the possibilities to replace or introduce new substituents on the core structure, which is of key importance to optimize compound properties or introduce probes to further expand the possibilities of these compounds as tailored research tools to study G4 biol. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4COA of Formula: C8H6N2O2).

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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.COA of Formula: 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

B(C₆F₅)₃-Catalyzed Direct C3 Alkylation of Indoles and Oxindoles was written by Basak, Shyam;Alvarez-Montoya, Ana;Winfrey, Laura;Melen, Rebecca L.;Morrill, Louis C.;Pulis, Alexander P.. And the article was included in ACS Catalysis in 2020.HPLC of Formula: 150560-58-0 This article mentions the following:

A new approach to the direct C3-alkylation of indoles and oxindoles using a B(C₆F₅)₃ catalyst and amine-derived alkylating agents to give arylated indole derivatives I [R = H, Me, n-hexyl, Bn; R¹ = H, Me, Ph; R² = H, 4-Me, 5-Cl, etc.; R³ = Me, Et, Bn, etc.] and oxindole derivatives II [R⁴ = H, 5-F, 6-Me, etc.; R⁵ = CO₂Et, Ph, 4-MeC₆H₄, etc.] were reported. Also this borane-catalyzed strategy in alkylation-ring opening cascade process to afford functionalized indoles III [R₆ = H, Me; R⁷ = H, Me; R⁸ = H, 5-OMe; R⁹ = 2,4,6-(Me)₃C₆H₂, 2-MeOC₆H₄, 2-Me-4-MeOC₆H₃, 2,6-(Me)₂-4-MeOC₆H₂] was reported. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0HPLC of Formula: 150560-58-0).

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.HPLC of Formula: 150560-58-0

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

Development of a Metal- and Oxidant-Free Enzyme-Photocatalyst Hybrid System for Highly Efficient C-3 Acylation Reactions of Indoles with Aldehydes was written by Yu, Yuan;Lin, Ru-De;Yao, Yao;Shi, Ming-Liang;Lu, Wei-Fan;Wang, Na;Yu, Xiao-Qi. And the article was included in ACS Catalysis in 2022.Formula: C11H11NO This article mentions the following:

An enzyme-photocatalyst hybrid system has been developed for aldehyde-based indole C-3 acylation. The concept of this process is to form a C-N bond through the three-component Mannich reaction of aldehydes RCHO (R = H, Ph, pyridin-2-yl, thiophen-2-yl, etc.), amines, such as 4-fluoroaniline, 2-aminopyrimidine and indoles I (R¹ = H, 4-Me, 5-F, 6-Cl, etc.; R² = Me, Ethyl; R³ = H, Me), thereby introducing an aminomethyl group on the indole ring. Next, this system catalyzed the formation of the corresponding imide ion from the Mannich product, followed by rapid hydrolysis to give the final C-3 carbonyl indole product II. More than 30 indole C-3 acylated products II (up to 93% yield) were successfully synthesized under mild conditions, and indole derivatization of two bioactive substances (probenecid and cholesterol) was realized. The mechanistic study provides theor. support for the construction of photoenzyme catalytic systems. This is an example of enzyme-light-activated C-3 acylation of indoles I under very mild reaction conditions, without the use of transition metal catalysts, metal salts, and addnl. oxidants. This efficient enzyme-photocatalyst hybrid system provides a strategy for the development of photoenzyme catalysis fields. In the experiment, the researchers used many compounds, for example, 1,4-Dimethyl-1H-indole-3-carbaldehyde (cas: 170489-16-4Formula: C11H11NO).

1,4-Dimethyl-1H-indole-3-carbaldehyde (cas: 170489-16-4) 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.Formula: C11H11NO

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

From Indoles to Carbazoles: Tandem Cp*Rh(III)-Catalyzed C-H Activation/Bronsted Acid-Catalyzed Cyclization Reactions was written by Wu, Jia-Qiang;Yang, Zhen;Zhang, Shang-Shi;Jiang, Chun-Yong;Li, Qingjiang;Huang, Zhi-Shu;Wang, Honggen. And the article was included in ACS Catalysis in 2015.Synthetic Route of C8H6N2O2 This article mentions the following:

A tandem Cp*Rh(III)-catalyzed C-H activation/Bronsted acid-catalyzed intramol. cyclization allows a facile synthesis of carbazoles from readily available indoles. The reaction proceeds under rather mild reaction conditions with the generation of water and N₂ as the only byproducts. Broad substrate scope, excellent functional group tolerance, and high yields were observed The benzannulation of pyrroles for the synthesis of indoles is also feasible using the same protocol. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Synthetic Route of C8H6N2O2).

6-Nitro-1H-indole (cas: 4769-96-4) 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. 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 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

Enantioselective Propargylation of Oxonium Ylide with α-Propargylic-3-Indolymethanol: Access to Chiral Propargylic Indoles was written by Liu, Xiangrong;Tian, Xue;Huang, Jiawu;Qian, Yu;Xu, Xinfang;Kang, Zhenghui;Hu, Wenhao. And the article was included in Organic Letters in 2022.Application of 827-01-0 This article mentions the following:

An enantioselective three-component reaction of diazoindolinones I (R¹ = 6-OMe, 5-Me, 5-Cl, etc.; R² = Me, Bn) with alc. R³OH (R³ = Me, benzyl, naphthalen-2-ylmethyl, etc.) and α-propargylic-3-indolymethanols II (R⁴ = TMS, TBS, TIPS, Ph, t-Bu; R⁵ = 7-Me, 5-OMe, 5-Cl, 6-OMe, 2-Ph) under cocatalysis of Rh(II) and chiral phosphoric acid (CPA) has been reported. It proceeds through the regio- and enantiospecific addition of the in situ formed oxonium ylide to the α-propargylic indole iminium ion that is generated from 3-indolyl propargylic alc. II with CPA. This work features an asym. counteranion-directed propargylation of oxonium ylide, and provides an efficient access to chiral propargylic indole derivatives syn-III and IV with high yields and enantioselectivities. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Application of 827-01-0).

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

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

Synthesis with acrylonitrile. XXI. Synthesis and properties of 1-indolepropionic acids was written by Terent’ev, A. P.;Kost, A. N.;Smit, V. A.. And the article was included in Zhurnal Obshchei Khimii in 1955.Recommanded Product: 3-(1H-Indol-1-yl)propanoic acid This article mentions the following:

It was shown that the 2-cyanoethyl group can be cleaved from indole ring if it is located in 1-position; the mol. is stable if the group is in the 3-position. To a stirred mixture of 11.7 g. indole, 10.6 g. CH₂:CHCN (Ia), and 50 mL. C₆H₆ was added 0.6 g. powd. KOH (exothermic reaction) and after 1-2 h. the mixture was filtered and distilled yielding 95% 1-indolepropionitrile, b₃ 168-80°, m. 47°. Refluxed with 10% KOH 3 h. it gave 95% 1-indolepropionic acid (I), m. 85-6° (crude), m. 90-1° (from aqueous EtOH-HCl). Heating 11.7 g. indole, 8 g. ethylene cyanohydrin, and 6 g. solid KOH in 100 mL. 95% EtOH in autoclave 6 h. at 190-200° gave 62% I; NaOH gave a 41% yield; the best yield was 90% attained with KOH in 6 h. at 220°. Similar reaction using EtOCH₂CH₂CN gave a 47% yield in 6 h. at 200°; in refluxing C₆H₆ only a 12% yield was obtained. The autoclave reaction as above of indole and Me₂NCH₂CH₂CN with solid KOH in 95% EtOH gave 53% I; only 15% was obtained in refluxing xylene. Stirring 3.9 g. 2-methylindole, 3.4 g. Ia, 0.2 g. powd. KOH and 15 mL. C₆H₆ 1 h. at room temperature and 1 h. at reflux gave 77% 2-methyl-1-indole-propionitrile, m. 83°, b₂ 170-80°; hydrolysis with KOH gave 2-methyl-1-indolepropionic acid, m. 111-12°. Similar reaction of 34 g. 3-indolepropionitrile (II) and 21.2 g. Ia with powd. KOH in C₆H₆ gave 97% 1,3-indolebispropionitrile, (III). m. 88-9°(crude). m. 96-7° (from EtOH): hydrolysis aqueous EtOH). Similar condensation of 2-methyl-3-indolepropionitrile with Ia gave 83% 2-methyl-1,3-indolebispropionitrile, m. 144-5° (from EtOH), which gave 100% of the dicarboxylic acid, m. 128° (from H₂O). Indole (5.8 g.), 10 g. EtO₂CCH:CH₂, and 0.3 g. powd. KOH stirred 1 h. at room temperature in 25 mL. C₆H₆, then refluxed 2 h. gave 30% Et 1-indolepropionate, b₂ 135-50°, which gave the free acid, m. 83-6°; this cleaves with superheated steam to indole. Similarly, 1,3-indolebispropionic acid with superheated steam at 280° gave 3-indolepropionic acid. Heating III with a little hydroquinone under N to 250° gave 92% II, m. 64°; refluxing I with 50% KOH 8 h. in NH₃ stream gave no indole and nearly all acid was recovered. However similar treatment of 1-indolepropionitrile gave about 10% indole and 80% I. In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1Recommanded Product: 3-(1H-Indol-1-yl)propanoic acid).

3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1) 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. 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.Recommanded Product: 3-(1H-Indol-1-yl)propanoic acid

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

Indole-Containing Amidinohydrazones as Nonpeptide, Dual RXFP3/4 Agonists: Synthesis, Structure-Activity Relationship, and Molecular Modeling Studies was written by Guan, Dongliang;Rahman, Toufiqur Md;Gay, Elaine A.;Vasukuttan, Vineetha;Mathews, Kelly M.;Decker, Ann M.;Williams, Alexander H.;Zhan, Chang-Guo;Jin, Chunyang. And the article was included in Journal of Medicinal Chemistry in 2021.Reference of 827-01-0 This article mentions the following:

Herein, the first structure-activity relationship studies of a series of novel nonpeptide amidinohydrazone-based agonists I [R¹ = H, 4-Me, 7-F, etc.; R² = H, Me; R³ = ; 4-ClC₆H₄, 3,4-di-ClC₆H₃, 2-thienyl, etc.; R⁴ = H, Me; n = 0,1,2,3], which were characterized by RXFP3 functional and radioligand binding assays was reported. Several potent and efficacious RXFP3 agonists compound I [R¹ = 5-CN-7-Me, R² = H, R³ = 4-CO₂MeC₆H₄, R⁴ = H, n = 2] were identified with EC₅₀ values <10 nM. These compounds also had high potency at RXFP4 but no agonist activity at RXFP1, demonstrating > 100-fold selectivity for RXFP3/4 over RXFP1. In vitro ADME and pharmacokinetic assessments revealed that the amidinohydrazone derivatives might have limited brain permeability. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Reference of 827-01-0).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Reference of 827-01-0

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

Direct N-H/α,α,β,β-C(sp³)-H functionalization of piperidine via an azomethine ylide route: synthesis of spirooxindoles bearing 3-substituted oxindoles was written by Du, Yanlong;Yu, Aimin;Jia, Jiru;Zhang, Youquan;Meng, Xiangtai. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2017.HPLC of Formula: 774-47-0 This article mentions the following:

A protocol for the direct functionalization of N-H/α,α,β,β-C(sp³)-H of piperidine without any metal or external oxidants was reported. This reaction was promoted by 4-(trifluoromethyl)benzoic acid via an azomethine ylide intermediate. This was a simple method for the synthesis of spirooxindoles bearing 3-substituted oxindole moieties. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0HPLC of Formula: 774-47-0).

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. 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: 774-47-0

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