05/01/2023 - Page 11 of 11 - Indole Building Blocks

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).

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

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).

Joshi, Shrinivas D. et al. published their research in Bioorganic Chemistry in 2017 | CAS: 24407-32-7

4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Safety of 4,5,6,7-Tetrabromoisoindoline-1,3-dione

Chemical synthesis and in silico molecular modeling of novel pyrrolyl benzohydrazide derivatives: Their biological evaluation against enoyl ACP reductase (InhA) and Mycobacterium tuberculosis was written by Joshi, Shrinivas D.;More, Uttam A.;Dixit, Sheshagiri R.;Balmi, Sunil V.;Kulkarni, Basavaraj G.;Ullagaddi, Geeta;Lherbet, Christian;Aminabhavi, Tejraj M.. And the article was included in Bioorganic Chemistry in 2017.Safety of 4,5,6,7-Tetrabromoisoindoline-1,3-dione This article mentions the following:

In efforts to develop new antitubercular agents, we report here the synthesis of a series of novel pyrrole hydrazine derivatives The mols. were evaluated against inhibitors of InhA, which is one of the key enzymes involved in type II fatty acid biosynthetic pathway of the mycobacterial cell wall as well as inhibitors of Mycobacterium tuberculosis H37Rv. The binding mode of compounds at the active site of enoyl-ACP reductase was explored using the surflex-docking method. The model suggests one or two H-bonding interactions between the compounds and the InhA enzyme. Some compounds exhibited good activities against InhA in addition to promising activities against M. tuberculosis. In the experiment, the researchers used many compounds, for example, 4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7Safety of 4,5,6,7-Tetrabromoisoindoline-1,3-dione).

Geng, Pengxin et al. published their research in Green Chemistry in 2019 | CAS: 5388-42-1

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

A g-C₃N₄-based heterogeneous photocatalyst for visible light mediated aerobic benzylic C-H oxygenations was written by Geng, Pengxin;Tang, Yurong;Pan, Guanglong;Wang, Wentao;Hu, Jinchuan;Cai, Yunfei. And the article was included in Green Chemistry in 2019.Safety of 2-Phenylisoindolin-1-one This article mentions the following:

A metal-free heterogeneous photocatalytic system has been developed for highly efficient benzylic C-H oxygenations using oxygen as an oxidant. This visible light mediated oxidation reaction utilizes graphitic carbon nitride (g-C₃N₄) as a recyclable, nontoxic and low cost photocatalyst. Mild reaction conditions allow for the generation of synthetically and biol. valued isochromannones, phthalides, isoquinolinones, isoindolinones and xanthones from readily accessible alkyl aromatic precursors in good yields. The heterogeneous nature of the g-C₃N₄ catalytic system enables easy recovery and recycling as well as the use in multiple runs without loss of activity. The synthetic utility of this “green” methodol. was further demonstrated by applying in bioactive and drug valued target syntheses. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Safety of 2-Phenylisoindolin-1-one).

Yu, Yuan et al. published their research in ACS Catalysis in 2022 | CAS: 170489-16-4

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

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).

Basak, Shyam et al. published their research in ACS Catalysis in 2020 | CAS: 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

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).

Zhang, Zhi-Guang et al. published their research in Synthesis in 2011 | CAS: 4583-55-5

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Synthetic Route of C10H10BrN

Efficient preparation of polyfunctional indoles via a zinc organometallic variation of the Fischer indole synthesis was written by Zhang, Zhi-Guang;Haag, Benjamin A.;Li, Jin-Shan;Knochel, Paul. And the article was included in Synthesis in 2011.Synthetic Route of C10H10BrN This article mentions the following:

Functionalized organozinc reagents readily react with various aryldiazonium salts furnishing regioselectively polyfunctional indoles after heating with microwave irradiation This new organometallic variation of the Fischer indole synthesis tolerates a wide range of functional groups and can be readily scaled up. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Synthetic Route of C10H10BrN).

Banu, Saira et al. published their research in Green Chemistry in 2021 | CAS: 4583-55-5

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) 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.Computed Properties of C10H10BrN

Auto-tandem PET and EnT photocatalysis by crude chlorophyll under visible light towards the oxidative functionalization of indoles was written by Banu, Saira;Choudhari, Shubham;Patel, Girija;Yadav, Prem P.. And the article was included in Green Chemistry in 2021.Computed Properties of C10H10BrN This article mentions the following:

A tandem photocatalytic approach utilizing the natural pigment chlorophyll in crude form to achieve photoinduced electron transfer (PET) and energy transfer (EnT) towards the oxidative functionalization of indoles I [R = H, 4-OMe, 4,6-difluoro, 5-Br, etc.; R¹ = H, Me, Et; R² = H, Me, Ph; R¹R² = -(CH₂)₄-, -(CH₂)₅-] was reported. Redox potentials, ESR, fluorescence quenching and UV experiments have evidenced the dual catalytic activity of chlorophyll. The highlight of the study is the auto-tandem photocatalytic role of chlorophyll to enable the green oxidation of indoles I using mol. oxygen as the oxidant, water as the reaction medium, and photochem. energy from the visible region of the spectrum. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Computed Properties of C10H10BrN).

Prasad, Bagineni et al. published their research in Chemistry – A European Journal in 2020 | CAS: 4769-96-4

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

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).