January 2023 - Page 15 of 26 - Indole Building Blocks

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).

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

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).

Bogdanov, Andrei V. et al. published their research in ChemistrySelect in 2019 | CAS: 150560-58-0

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) 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 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). SDS of cas: 150560-58-0

Synthesis and Biological Evaluation of New Isatin-Based QACs with High Antimicrobial Potency was written by Bogdanov, Andrei V.;Zaripova, Ilyuza F.;Voloshina, Alexandra D.;Sapunova, Anastasia S.;Kulik, Natalia V.;Bukharov, Sergey V.;Voronina, Julia K.;Vandyukov, Alexander E.;Mironov, Vladimir F.. And the article was included in ChemistrySelect in 2019.SDS of cas: 150560-58-0 This article mentions the following:

A simple and easy condensation reaction of aryl- or N-substituted isatins with Girard’s reagents P and T was described for the synthesis of water-soluble isatin-3-acylhydrazone-based quaternary ammonium compounds (QACs) I [R = H, F, Br; R¹ = H, Me, OMe, etc.; R² = H, Br; R³ = H, Et, NO₂, etc.; R⁴ = H, (3,5-ditert-butyl-4-hydroxy-phenyl)methyl; R⁵ = trimethylammonio, pyridinium-1-yl] with high yields. Synthesized compounds were evaluated for their antibacterial and antifungal activities against Gram-pos. bacteria (S. aureus 209p and B. cereus 8035) and yeast-like fungus C. albicans 855-653. Among them three compounds I [R = H; R¹ = Me, Et, F, Br; R² = H; R³ = H; R⁴ = (3,5-ditert-butyl-4-hydroxy-phenyl)methyl; R⁵ = pyridinium-1-yl] exhibited very promising antibacterial activities. The influence of the substituent’s nature as in the aromatic fragment as at position 1 on the activity was established. The structures of all novel compounds I were fully characterized using IR and NMR spectroscopies as well as XRD anal. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0SDS of cas: 150560-58-0).

Jaiswal, Komal et al. published their research in ACS Organic & Inorganic Au in 2022 | 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. 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). Formula: C8H6N2O2

Dual Role of MoS₂ Quantum Dots in a Cross-Dehydrogenative Coupling Reaction was written by Jaiswal, Komal;Girish, Yarabahally R.;Behera, Pradipta;De, Mrinmoy. And the article was included in ACS Organic & Inorganic Au in 2022.Formula: C8H6N2O2 This article mentions the following:

Modern day research focuses on the development of greener and eco-friendlier protocols to fabricate biol. relevant targets with minimal waste generation. C-C bond formation reactions are of prime importance in this regard. In a typical photocatalytic hydrogen evolution reaction (HER) three components are used, viz, catalyst, photosensitizer and sacrificial amine donor. Among these, the photosensitizer and sacrificial amine donors are wasted at the end of the reaction. Considering these drawbacks, in this work, we have developed a methodol. targeted at the utilization of sacrificial amine donors for C-H functionalization with MoS₂ Quantum Dots (QDs) as the catalyst as well as photosensitizer. QDs indeed emerged to be an active participant in heterogeneous electron transfer (HET) process. This concept opens up new possibilities in the field of nanomaterial-based photomediated organic transformations without the aid of any external photosensitizers via a clean and sustainable protocol with no side product. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Formula: C8H6N2O2).

Witt, Jonathan O. et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2016 | 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 827-01-0

Synthesis and characterization of a series of chiral alkoxymethyl morpholine analogs as dopamine receptor 4 (D₄R) antagonists was written by Witt, Jonathan O.;McCollum, Andrea L.;Hurtado, Miguel A.;Huseman, Eric D.;Jeffries, Daniel E.;Temple, Kayla J.;Plumley, Hyekyung C.;Blobaum, Anna L.;Lindsley, Craig W.;Hopkins, Corey R.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2016.Recommanded Product: 827-01-0 This article mentions the following:

Herein, we report the synthesis and structure-activity relationship of a series of chiral alkoxymethyl morpholine analogs. Our efforts have culminated in the identification of (S)-2-(((6-chloropyridin-2-yl)oxy)methyl)-4-((6-fluoro-1H-indol-3-yl)methyl)morpholine(I) as a novel potent and selective dopamine D4 receptor antagonist with selectivity against the other dopamine receptors tested (<10% inhibition at 1 μM against D₁, D_2L, D_2S, D₃, and D₅). In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Recommanded Product: 827-01-0).