Month: January 2023

Synthesis of substituted carbazoles and β-carbolines by cyclization of diketoindole derivatives was written by Duval, Eric;Cuny, Gregory D.. And the article was included in Tetrahedron Letters in 2004.Name: 2-(5-Chloro-1H-indol-3-yl)acetic acid This article mentions the following:

A new route to substituted β-carbolines and carbazoles is described. Diketoindole intermediates, prepared by Friedel-Crafts acylations of 3-substituted indoles, were converted to 3-hydroxycarbazoles and β-carbolines in good yields, 51-96% and 82-97%, resp. This method also allows for the formation of 4-substituted β-carbolines. The application of this methodol. to the synthesis of the natural products hyellazole and 6-chlorohyellazole is also described. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Name: 2-(5-Chloro-1H-indol-3-yl)acetic acid).

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Name: 2-(5-Chloro-1H-indol-3-yl)acetic 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

Catalytic methylation of C-H bonds using CO₂ and H₂ was written by Li, Yuehui;Yan, Tao;Junge, Kathrin;Beller, Matthias. And the article was included in Angewandte Chemie, International Edition in 2014.Application of 4583-55-5 This article mentions the following:

Formation of C-C bonds from CO₂ is a much sought after reaction in organic synthesis. To date, other than C-H carboxylations using stoichiometric amounts of metals, base, or organometallic reagents, little is known about C-C bond formation. In fact, to the best of the authors’ knowledge, no catalytic methylation of C-H bonds using CO₂ and H₂ was reported. Herein, the combination of CO₂ and H₂ is described for efficient methylation of C-nucleophiles such as indoles, pyrroles, and electron-rich arenes. Comparison experiments which employ paraformaldehyde show similar reactivity for the CO₂/H₂ system. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Application of 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Application of 4583-55-5

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

Iron-Catalyzed C3-Formylation of Indoles with Formaldehyde and Aqueous Ammonia under Air was written by Wang, Qing-Dong;Zhou, Bin;Yang, Jin-Ming;Fang, Dong;Ren, Jiangmeng;Zeng, Bu-Bing. And the article was included in Synlett in 2017.Recommanded Product: 4769-96-4 This article mentions the following:

An efficient iron-catalyzed C3-selective formylation of free (N-H) or N-substituted indoles such as 2-phenyl-1H-indole, 6-fluoro-1H-indole, 1-methyl-1H-indole, etc. was developed by employing formaldehyde and aqueous ammonia, with air as the oxidant. This new method gave 3-formylindoles such as 2-phenyl-1H-indole-3-carbaldehyde, 6-fluoro-1H-indole-3-carbaldehyde, 1-methyl-1H-indole-3-carbaldehyde, etc. in moderate to excellent yields with fairly short reaction times. Moreover, this procedure for catalytic formylation of indoles can be applied to gram-scale syntheses. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Recommanded Product: 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Recommanded Product: 4769-96-4

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

Scaffold-Inspired Enantioselective Synthesis of Biologically Important Spiro[pyrrolidin-3,2′-oxindoles] with Structural Diversity through Catalytic Isatin-Derived 1,3-Dipolar Cycloadditions was written by Shi, Feng;Tao, Zhong-Lin;Luo, Shi-Wei;Tu, Shu-Jiang;Gong, Liu-Zhu. And the article was included in Chemistry – A European Journal in 2012.Product Details of 774-47-0 This article mentions the following:

Catalytic asym. construction of the biol. important spiro[pyrrolidin-3,2′-oxindole] scaffold with contiguous quaternary stereogenic centers in excellent stereoselectivities (up to >99:1 d.r., 98 % ee) has been established by using an organocatalytic 1,3-dipolar cycloaddition of isatin-based azomethine ylides. This protocol represents the first example of catalytic asym. 1,3-dipolar cycloadditions involving azomethine ylides generated in situ from unsym. cyclic ketones. In addition, theor. calculations were performed on the transition state of the reaction to understand the stereochem. Preliminary bioassays with these spiro[pyrrolidin-3,2′-oxindole] revealed that several compounds showed moderate cytotoxicity to SW116 cells. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Product Details of 774-47-0).

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Product Details of 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

Unexpected synthesis of azepino[4,3,2-cd]indoles from 4-aminoindoles was written by Halaiev, Olexandr;Garazd, Myroslav;Gzella, Andrzej;Lesyk, Roman. And the article was included in Tetrahedron Letters in 2017.Quality Control of 1-Methyl-1H-indol-4-amine This article mentions the following:

Synthesis of azepinoindoles I [R = Me, CH(Me)₂, CH₂C₆H₅, etc.] instead of quinolines from the regioselective Skraup-Doebner-Von Miller reaction of 4-aminoindoles and acetone in the presence of hydrochloric acid as a catalyst was developed. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-indol-4-amine (cas: 85696-95-3Quality Control of 1-Methyl-1H-indol-4-amine).

1-Methyl-1H-indol-4-amine (cas: 85696-95-3) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Quality Control of 1-Methyl-1H-indol-4-amine

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

Aerobic α-Oxidation of N-Substituted Tetrahydroisoquinolines to Dihydroisoquinolones via Organo-photocatalysis was written by Aganda, Kim Christopher C.;Hong, Boseok;Lee, Anna. And the article was included in Advanced Synthesis & Catalysis in 2019.Computed Properties of C14H11NO This article mentions the following:

An efficient visible-light-induced α-oxidation of N-substituted tetrahydroisoquinolines to dihydroisoquinolones I (R¹ = H, OMe; R² = Me, Ph, 2-pyridyl, etc.) has been developed using eosin Y as an organo-photocatalyst and oxygen as a green oxidant. The reactions were carried out under mild reaction conditions; the desired dihydroisoquinolones were obtained in up to 96% yield at room temperature under oxygen atm. This transformation provides a convenient route to dihydroisoquinolones with a wide range of substrates. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Computed Properties of C14H11NO).

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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Computed Properties of C14H11NO

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

Discovery of IDO1 and DNA dual targeting antitumor agents was written by Fang, Kun;Wu, Shanchao;Dong, Guoqiang;Wu, Ying;Chen, Shuqiang;Liu, Jianhe;Wang, Wei;Sheng, Chunquan. And the article was included in Organic & Biomolecular Chemistry in 2017.Reference of 4769-96-4 This article mentions the following:

The development of small mols. for cancer immunotherapy is highly challenging and indoleamine 2,3-dioxygenase 1 (IDO1) represents a promising target. Inspired by the synergistic effects between IDO1 inhibitors and traditional antitumor chemotherapeutics, the first orally active dual IDO1 and DNA targeting agents were designed by the pharmacophore fusion strategy. The bifunctional hybrids exhibited enhanced IDO1 enzyme inhibitory activity and in vitro cytotoxicity as compared to IDO1 inhibitor 1-methyl-tryptophan and DNA alkylating agent melphalan. In a murine LLC tumor model, the dual targeting agents demonstrated excellent antitumor efficacy, highlighting the advantages of this novel design strategy to improve the efficacy of small mol. cancer immunotherapy. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Reference of 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Reference of 4769-96-4

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

α-Arylidene Diacylglycerol-Lactones (DAG-Lactones) as Selective Ras Guanine-Releasing Protein 3 (RasGRP3) Ligands was written by Ann, Jihyae;Czikora, Agnes;Saini, Amandeep S.;Zhou, Xiaoling;Mitchell, Gary A.;Lewin, Nancy E.;Peach, Megan L.;Blumberg, Peter M.;Lee, Jeewoo. And the article was included in Journal of Medicinal Chemistry in 2018.Name: 5-Chloroindole-3-carboxaldehyde This article mentions the following:

Diacylglycerol-lactones have proven to be a powerful template for the design of potent ligands targeting C1 domains, the recognition motif for the cellular second messenger diacylglycerol. A major objective has been to better understand the structure activity relations distinguishing the seven families of signaling proteins that contain such domains, of which the protein kinase C (PKC) and RasGRP families are of particular interest. Here, we synthesize a series of aryl/alkyl substituted diacylglycerol-lactones and probe their relative selectivities for RasGRP3 vs. PKC. Compound I showed 72.6-fold selectivity relative to PKC alpha and 45.1-fold selectivity relative to PKC epsilon for in vitro binding activity. Likewise, in intact cells compound I induced Ras activation, a downstream response to RasGRP stimulation, with 8-29 fold selectivity relative to PKC delta S299 phosphorylation, a measure of PKC delta stimulation. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Name: 5-Chloroindole-3-carboxaldehyde).

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

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

Copper-Mediated Cyclization of o-Hydroxyaryl Enaminones with 3-Indoleacetic Acids toward the Synthesis of 3-Indolmethyl-Chromones was written by Wen, Kangmei;Li, Yinyan;Gao, Qiwen;Chen, Jiewen;Yang, Jie;Tang, Xiaodong. And the article was included in Journal of Organic Chemistry in 2022.Synthetic Route of C10H8ClNO2 This article mentions the following:

A copper-mediated tandem decarboxylative coupling/annulation protocol of o-hydroxyaryl enaminones with 3-indoleacetic acids. A series of 3-indolmethyl-chromones were afforded in up to 97% yield. A one-pot method for 3-indolmethyl-chromones from o-hydroxy acetophenones, N, N-dimethylformamide di-Me acetal, and 3-indoleacetic acids was also developed. Derivatization of the products was conducted to provide various indolmethyl-substituted pyrimidines. Moreover, a biol. evaluation revealed that some compounds had anti-influenza viral activities. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Synthetic Route of C10H8ClNO2).

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) 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. 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 C10H8ClNO2

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