January 2023 - Page 14 of 26 - Indole Building Blocks

Du, Yanlong et al. published their research in Chemical Communications (Cambridge, United Kingdom) in 2017 | CAS: 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

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).

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

Markova, Larysa I. et al. published their research in Dyes and Pigments in 2013 | CAS: 146368-07-2

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) 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.Category: indole-building-block

Comparison of a series of hydrophilic squaraine and cyanine dyes for use as biological labels was written by Markova, Larysa I.;Terpetschnig, Ewald A.;Patsenker, Leonid D.. And the article was included in Dyes and Pigments in 2013.Category: indole-building-block This article mentions the following:

Unlike cyanine dyes, which are widely used as fluorescent probes and labels for biomedical applications squaraine dyes are less investigated. A series of monoreactive, water-soluble, squaraine dyes with two aromatic sulfo groups and up to 3 sulfobutyl groups was synthesized and the spectral properties of these dyes were compared to dicarbocyanines of identical structure. Compared to the cyanines in aqueous solutions the squaraine dyes absorb and emit at shorter wavelengths (630-636 nm/639-645 nm vs. 647-653 nm/665-672 nm), have higher molar absorptivities (284,000-333,000 M^-1 cm^-1vs. 242,000-260,000 M^-1 cm^-1), lower fluorescence quantum yields (4.3-9.4% vs. 27-32%) and lower fluorescence lifetimes (0.2-0.3 ns vs. 1.0-1.2 ns) but the quantum yields and lifetimes substantially increase when bound to proteins (Bovine Serum Albumin (BSA) or antibodies, IgG (IgG)). Squaraines with two aromatic sulfo groups show no aggregation tendency up to concentrations of 2 × 10^-4 M while the corresponding cyanine dye is free of aggregation up to 5 × 10^-4 M. The increase in the number of sulfobutyl groups bears a strong influence on the aggregation tendency of both dye classes upon covalent labeling to BSA and IgG resulting in increased quantum yields and lifetimes of the protein conjugates. Compared to cyanines, squaraine dyes exhibit higher photostabilities and much higher sensitivity of the quantum yields and fluorescence lifetimes toward the microenvironment and are therefore better suited as fluorescence sensors. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Category: indole-building-block).

Fukuda, Yasumichi et al. published their research in Journal of Medicinal Chemistry in 1999 | CAS: 210345-56-5

Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5) 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. 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: 210345-56-5

Novel cyclopropapyrroloindole derivative (AT-3510) bearing methoxycarbonyl and trifluoromethyl groups was written by Fukuda, Yasumichi;Furuta, Hirosuke;Kusama, Yoshie;Ebisu, Hiroyuki;Oomori, Yasuo;Terashima, Shiro. And the article was included in Journal of Medicinal Chemistry in 1999.HPLC of Formula: 210345-56-5 This article mentions the following:

The seco-Cl 3-methoxycarbonyl-2-trifluoromethylcyclopropapyrroloindole (MCTFCPI) derivatives dl- and/or (S)-I [Ar = Q, Q₁, Q₂, Q₃, R = 4,5,6-(MeO)₃, 5,6,7-(MeO)₃, 5-MeO, etc., X = NH, O, CH, Y = CH, N] carrying various acyl moieties at the N6-position were synthesized along with their prodrugs (S)-II, and their antitumor activity was evaluated. Among these derivatives, AT-3510 [(S)-II (Ar = Q¹, R = 7-MeO, X = O)], the novel prodrug MCTFCPI derivative carrying a 5-(7-methoxybenzofuran-2-ylcarbonyl)aminoindole-2-carbonyl group at the N6-position, was found to exhibit more excellent antitumor activity against human tumor xenografts than the clin. trial candidates carzelesin and KW-2189 (III) and cisplatin. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5HPLC of Formula: 210345-56-5).

Dhawan, Sanjeev et al. published their research in Journal of Chemical and Pharmaceutical Research in 2016 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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: 2-(Phenylthio)isoindoline-1,3-dione

Strategies for chemical synthesis of pyrazolone derivatives and their bio-significance was written by Dhawan, Sanjeev;Narang, Rakesh;Khatik, Gopal L.;Chopra, Harish Kumar;Nayak, Surendra Kumar. And the article was included in Journal of Chemical and Pharmaceutical Research in 2016.Recommanded Product: 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:

Over the last few decades, pyrazolone derivatives have been used for various biochem. applications. Some of these derivatives such as metamizole, phenazone, aminopyrine and propyphenazone, are widely used as antiinflammatory and analgesics. Moreover, pyrazolones have been exhibited antioxidant, antibacterial, anticancer and several other biol. activities. Thus, keeping in view of their importance, synthetic strategies for existing as well as novel pyrazolone derivatives have been developed and explored their biochem. utility. As versatile features of pyrozaolones have emerged, so the aim of the present paper is to put chem. synthetic schemes and biol. advancements of pyrazolone derivatives together. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Recommanded Product: 2-(Phenylthio)isoindoline-1,3-dione).

Rogness, Donald C. et al. published their research in Tetrahedron Letters in 2009 | CAS: 210345-56-5

Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Quality Control of Methyl 5-bromo-1H-indole-2-carboxylate

Rapid synthesis of the indole-indolone scaffold via [3+2] annulation of arynes by methyl indole-2-carboxylates was written by Rogness, Donald C.;Larock, Richard C.. And the article was included in Tetrahedron Letters in 2009.Quality Control of Methyl 5-bromo-1H-indole-2-carboxylate This article mentions the following:

The reaction of Me indole-2-carboxylates, e.g., I, and arynes afforded a very efficient, high yielding synthesis of a novel indole-indolone ring system, e.g., II, which tolerated considerable functionality, was broad in scope, and proceeded under mild reaction conditions. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5Quality Control of Methyl 5-bromo-1H-indole-2-carboxylate).

Guan, Dongliang et al. published their research in Journal of Medicinal Chemistry in 2021 | CAS: 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

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).

Chaudhari, Chandan et al. published their research in Green Chemistry in 2020 | 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Application In Synthesis of 2-Phenylisoindolin-1-one

One-pot synthesis of pyrrolidones from levulinic acid and amines/nitroarenes/nitriles over the Ir-PVP catalyst was written by Chaudhari, Chandan;Shiraishi, Masaya;Nishida, Yoshihide;Sato, Katsutoshi;Nagaoka, Katsutoshi. And the article was included in Green Chemistry in 2020.Application In Synthesis of 2-Phenylisoindolin-1-one This article mentions the following:

The synthesis of pyrrolidones I (R = C₆H₅, CH₂C₆H₅, 4-FC₆H₄, etc.) via reductive amination of levulinic acid with aniline was examined over polypyrrolidone-stabilized metal nanoparticle catalysts. Among them, Ir metal was the most effective and applicable for the reductive amination of levulinic acid with nitroarenes R¹NO₂ (R¹ = C₆H₅, 4-CH₃OC₆H₄, 4-CH₃C₆H₄, 4-ClC₆H₄, 4-FC₆H₄)/nitriles R²CN (R² = C₆H₅, 4-CH₃OC₆H₄, 4-CH₃C₆H₄, 4-ClC₆H₄, 4-CF₃C₆H₄). Importantly, this catalyst was used for the one-pot synthesis of the anti-inflammatory drug indoprofen from 2-formylbenzoic acid and 2-(4-nitrophenyl)propanoic acid. 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).

Terent’ev, A. P. et al. published their research in Zhurnal Obshchei Khimii in 1955 | CAS: 6639-06-1

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

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).

Liu, Xiangrong et al. published their research in Organic Letters in 2022 | CAS: 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

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).

Wu, Jia-Qiang et al. published their research in ACS Catalysis in 2015 | CAS: 4769-96-4

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

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).