20/02/2023 - Page 7 of 14 - Indole Building Blocks

Baykal, Aslihan et al. published their research in European Journal of Organic Chemistry in 2020 | 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Recommanded Product: 210345-56-5

A Bu₄N[Fe(CO)₃(NO)]-Catalyzed Hemetsberger-Knittel Indole Synthesis was written by Baykal, Aslihan;Plietker, Bernd. And the article was included in European Journal of Organic Chemistry in 2020.Recommanded Product: 210345-56-5 This article mentions the following:

The nucleophilic Fe complex Bu₄N[Fe(CO)₃(NO)] (TBA[Fe]) catalyzes the direct intramol. amination of aryl vinyl azides RCH=C(N₃)C(O)R¹ (R = 3,4-dimethoxyphenyl, 4,5-dimethylfuran-2-yl, naphthalen-1-yl, etc.; R¹ = Ph, OMe, morpholin-4-yl, etc.) to give the corresponding indole derivatives I (R² = H, F, CN, dimethylaminyl, etc.; R³ = H, Br, OMe; R⁴ = H, Br, Me, OMe; R³R⁴ = -(CH=CH-CH=CH)-; R⁵ = H, Me), Me 2,3-dimethyl-4H-furo[3,2-b]pyrrole-5-carboxylate and Me pyrazolo[1,5-a]pyridine-2-carboxylate in good to excellent yields. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5Recommanded Product: 210345-56-5).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from闂佽壈浜崹淇沜illus thuringiensis闂佽壈浜粋鍧闂佽壈浜崹淇沜illus velezensis闂佽壈浜粋鍧 their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Zhang, Shunji et al. published their research in Youji Huaxue in 2020 | CAS: 4769-96-4

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

Sulfuric acid catalyzed rapid nucleophilic substitution of propargyl alcohols was written by Zhang, Shunji;Liu, Huili. And the article was included in Youji Huaxue in 2020.Recommanded Product: 6-Nitro-1H-indole This article mentions the following:

Sulfuric acid efficiently catalyzes the direct substitution of the hydroxyl group of propargylic alcs. R¹C(OH)CCR² (R¹ = 3,4-dimethoxyphenyl, 4-(benzyloxy)phenyl, 3-(trifluoromethyl)phenyl, etc.; R² = pentyl, Ph, 4-methoxyphenyl) with a variety of C- and O-based nucleophiles such as isopropanol, phenol, furan, etc. to aid C-C and C-O bond formation. The reactions can be performed in an undried solvent under air atm. to obtain the desired products R¹C(R³)CCR² (R³ = OMe, furan-2-yl, 4-hydroxyphenyl, etc.) in good yields. In most cases, the reaction proceeds to completion in 1 min at room temperature In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Recommanded Product: 6-Nitro-1H-indole).

Porobic, Ivana et al. published their research in Bioorganic & Medicinal Chemistry in 2013 | CAS: 1912-45-4

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) 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.Quality Control of 2-(5-Chloro-1H-indol-3-yl)acetic acid

Molecular recognition of indole derivatives by polymers imprinted with indole-3-acetic acid: A QSPR study was written by Porobic, Ivana;Kontrec, Darko;Soskic, Milan. And the article was included in Bioorganic & Medicinal Chemistry in 2013.Quality Control of 2-(5-Chloro-1H-indol-3-yl)acetic acid This article mentions the following:

Three molecularly imprinted polymers (MIPs) were prepared using the phytohormone indole-3-acetic acid (IAA) as a template mol., 4-vinylpyridine (MIP-1 and MIP-2) or N,N-dimethylaminoethyl methacrylate (MIP-3) as functional monomers, ethylenglycol dimethacrylate as a cross linker and acetonitrile (MIP-1), a methanol-water mixture (MIP-2) or chloroform (MIP-3) as porogens. Retention factors for IAA and 29 indole derivatives were determined by high-performance liquid chromatog., using the molecularly imprinted polymers as stationary phases and acetonitrile as an eluent. High correlations between selectivity factors of above mentioned polymers indicate that their retention mechanisms are basically the same. A quant. structure-property relationships anal. revealed that the presence of the terminal carboxyl group on the 3-side chain plays an essential role in the binding of the indole derivatives to the polymers. The derivatives without the carboxyl group exhibit a drastically lower affinity toward the polymers. Another factor which favors the binding is electronic d. of indole nucleus. Substituents with electro-withdrawing properties enhance the binding, while electro-donating substituents have the opposite effect. The length of the 3-side chain also affects the binding. Indole-3-carboxylic acid having the carboxyl group directly attached to the ring as well as the derivatives whose side chain is longer than that of IAA bind to the polymers with a lower affinity. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Quality Control of 2-(5-Chloro-1H-indol-3-yl)acetic acid).

Muvvala, Subhashini et al. published their research in ChemistrySelect in 2022 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. 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.Name: 2-Phenylisoindolin-1-one

Microwave-Assisted Reductive Amination of 2-Carboxybenzaldehydes with Amines for the Synthesis of N-Substituted Isoindolin-1-ones was written by Muvvala, Subhashini;Kumari, Krishnaiah;Miriyala, Venkatesh;Mogili, Padma;Chidara, Sridhar;Maddirala, Shambabu Joseph;Saxena, Abhishek;Behera, Manoranjan. And the article was included in ChemistrySelect in 2022.Name: 2-Phenylisoindolin-1-one This article mentions the following:

Microwave-assisted, transition metal free methodol. for the synthesis of N-substituted isoindolin-1-ones I [R¹ = H, F; R² = i-Pr, Ph, PhCH₂, 2-(piperidin-1-yl)ethyl, etc.] from 2-carboxybenzaldehydes II and various amines R²NH₂ by reductive amination reaction using formic acid has been described. This method is relatively simple, benign, safe and tolerates a variety of functional groups. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Name: 2-Phenylisoindolin-1-one).

Carrillo, Adela I. et al. published their research in Reaction Chemistry & Engineering in 2018 | CAS: 5388-42-1

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

A versatile, immobilized gold catalyst for the reductive amination of aldehydes in batch and flow was written by Carrillo, Adela I.;Llanes, Patricia;Pericas, Miquel A.. And the article was included in Reaction Chemistry & Engineering in 2018.SDS of cas: 5388-42-1 This article mentions the following:

An efficient and environmentally friendly catalytic route for the reductive amination of carbonyl compounds has been designed. First, a one-pot procedure has been followed for the synthesis and incorporation of gold nanoparticles (AuNPs) into a mesoporous silica solid by using light as an abundant and clean energy source. Then, the as-prepared material has been successfully employed as a heterogeneous catalyst in the production of secondary and tertiary amines by reductive amination using Ph(Me)2SiH as the reducing agent. The endurance of the catalyst has been demonstrated in batch, and a continuous flow process allowing the safe preparation of multigram amounts of reductive amination products (accumulated TON = 434 in 18 h operation involving 6 sequential examples) has been implemented. The scope of the reaction has also been extended to the synthesis of more challenging active pharmaceutical ingredients (APIs), such as indoprofen precursors and biomass-derived products, which were obtained in good to excellent yields. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1SDS of cas: 5388-42-1).

Surya Prakash Rao, H. et al. published their research in Synthetic Communications in 2022 | CAS: 5388-42-1

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

Palladium-catalyzed intramolecular C-N coupling: Facile synthesis of tetracyclic C(3)-aminoisoindolinones was written by Surya Prakash Rao, H.;Prabhakaran, J.. And the article was included in Synthetic Communications in 2022.HPLC of Formula: 5388-42-1 This article mentions the following:

Herein, a new methodol. to access tetracyclic heterocyclic compounds incorporating fused isoindolinone and benzimidazoline or isoindolinone and quinazoline motifs was reported. The palladium-(II) catalyzed intramol. Buchwald-Hartwig C-N coupling involving the C(3) amino and the N(2) 2-bromophenyl groups provided coveted heterocycles in excellent yields. The methodol. was versatile, highly efficient and has a wide scope for the synthesis of a range of medicinally important tetracyclic C(3)-aminoisoindolinones. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1HPLC of Formula: 5388-42-1).

Wu, Zhiqiang et al. published their research in Synthetic Communications in 2021 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Related Products of 4769-96-4

Solvent-free multi-component synthesis of unsymmetrical bis(indolyl)alkanes with Lewis acid-surfactant-SiO₂ as nanocatalyst was written by Wu, Zhiqiang;Wang, Gang;Li, Zhenliang;Feng, Enke;Liang, Yanping;Zhan, Haijuan;Liu, Wanyi. And the article was included in Synthetic Communications in 2021.Related Products of 4769-96-4 This article mentions the following:

Herein, the multicomponent synthesis of the bis(indolyl)methane derivatives in a ball mill were reported. The reaction was carried out under solvent-free conditions using only the Lewis acid-surfactant-SiO₂ composite nanocatalyst (LASSC) prepared in situ. The unsym. bis(indolyl) methane derivatives containing nitro or fluorine substitution with a yield of 72%-92% were obtained in a short reaction time. Under the action of the verified combined catalyst of AlCl₃闁?H₂O + SDS + SiO₂, the method of preparing unsym. bis(indolyl)methane by mech. grinding without solvent was obvious advantages. Finally, the catalysis system was used eight times without a significant decrease in activity were inspected. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Related Products of 4769-96-4).

Rodrigues, Tiago et al. published their research in Angewandte Chemie, International Edition in 2015 | CAS: 827-01-0

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

Multidimensional De Novo Design Reveals 5-HT_2B Receptor-Selective Ligands was written by Rodrigues, Tiago;Hauser, Nadine;Reker, Daniel;Reutlinger, Michael;Wunderlin, Tiffany;Hamon, Jacques;Koch, Guido;Schneider, Gisbert. And the article was included in Angewandte Chemie, International Edition in 2015.Application of 827-01-0 This article mentions the following:

The authors report a multi-objective de novo design study driven by synthetic tractability and aimed at the prioritization of computer-generated 5-HT_2B receptor ligands with accurately predicted target-binding affinities. Relying on quant. bioactivity models the authors designed and synthesized structurally novel, selective, nanomolar, and ligand-efficient 5-HT_2B modulators with sustained cell-based effects. The authors’ results suggest that seamless amalgamation of computational activity prediction and mol. design with microfluidics-assisted synthesis enables the swift generation of small mols. with the desired polypharmacol. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Application of 827-01-0).

Kim, Ji Hye et al. published their research in Angewandte Chemie, International Edition in 2020 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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. 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: C14H9NO2S

Divergent Strain-Release Amino-Functionalization of [1.1.1]Propellane with Electrophilic Nitrogen-Radicals was written by Kim, Ji Hye;Ruffoni, Alessandro;Al-Faiyz, Yasair S. S.;Sheikh, Nadeem S.;Leonori, Daniele. And the article was included in Angewandte Chemie, International Edition in 2020.Formula: C14H9NO2S This article mentions the following:

Herein the authors report the development of a photocatalytic strategy for the divergent preparation of functionalized bicyclo[1.1.1]pentylamines. This approach exploits, for the first time, the ability of nitrogen-radicals to undergo strain-release reaction with [1.1.1]propellane. This reactivity is facilitated by the electrophilic nature of these open-shell intermediates and the presence of strong polar effects in the transition-state for C-N bond formation/ring-opening. With the aid of a simple reductive quenching photoredox cycle, the authors have successfully harnessed this novel radical strain-release amination as part of a multicomponent cascade compatible with several external trapping agents. Overall, this radical strategy enables the rapid construction of novel amino-functionalized building blocks with potential application in medicinal chem. programs as p-substituted aniline bioisosteres. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Formula: C14H9NO2S).

Sashidhara, Koneni V. et al. published their research in European Journal of Medicinal Chemistry in 2014 | CAS: 827-01-0

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

Design and synthesis of novel indole-chalcone fibrates as lipid lowering agents was written by Sashidhara, Koneni V.;Dodda, Ranga Prasad;Sonkar, Ravi;Palnati, Gopala Reddy;Bhatia, Gitika. And the article was included in European Journal of Medicinal Chemistry in 2014.Application In Synthesis of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

A series of novel indole-chalcone fibrates were synthesized and their hypolipidemic activity was evaluated in triton WR-1339 induced hyperlipidemic rat model. Preliminary studies indicated that three hybrids, e.g., I, exhibited potent in vitro antioxidant and significant in vivo antidyslipidemic effects. The results results suggest that these new hybrid scaffolds may serve as promising leads for the development of next generation lipid lowering agents. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Application In Synthesis of 5-Chloroindole-3-carboxaldehyde).