Category: indole-building-block

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

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

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

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

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

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

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

Extending the versatility of the Hemetsberger-Knittel indole synthesis through microwave and flow chemistry was written by Ranasinghe, Nadeesha;Jones, Graham B.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2013.Category: indole-building-block This article mentions the following:

Microwave, flow and combination methodologies were applied to the synthesis of a number of substituted indoles. Based on the Hemetsberger-Knittel (HK) process, modifications allow formation of products rapidly and in high yield. Adapting the methodol. allows formation of 2-unsubstituted indoles and derivatives, and a route to analogs of the antitumor agent PLX-4032 is demonstrated. The utility of the HK substrates is further demonstrated through bioconjugation and subsequent ring closure and via Huisgen type [3+2] cycloaddition chem., allowing formation of peptide adducts which can be subsequently labeled with fluorine tags. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5Category: indole-building-block).

Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Category: indole-building-block

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

Synthesis, characterization and anticancer activity of certain 3-{4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenylimino}indolin-2-one derivatives was written by Gudipati, Rajyalakshmi;Anreddy, Rama Narsimha Reddy;Manda, Sarangapani. And the article was included in Saudi Pharmaceutical Journal in 2011.Recommanded Product: 112656-95-8 This article mentions the following:

Series of 5- or 7-substituted 3-{4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenylimino}-indolin-2-one derivatives were synthesized by treating 5-(4-aminophenyl)-1,3,4-oxadiazole-2-thiol with different isatin derivatives The newly synthesized compounds were characterized on the basis of spectral (FT-IR, ¹H NMR, MS) analyses. All the synthesized derivatives were screened for anticancer activity against HeLa cancer cell lines using MTT assay. All the synthetic compounds produced a dose dependent inhibition of growth of the cells. The IC₅₀ values of all the synthetic test compounds were found between 10.64 and 33.62 μM. The potency (IC₅₀ values) of anticancer activity of the the halo-substituted compounds was comparable with that of known anticancer agent, Cisplatin. Among the synthesized 2-indolinones, these halo-substituted compounds with halogen atom (electron withdrawing groups) at C5 position showed the most potent activity. These results indicate that C5 substituted derivatives may be useful leads for anticancer drug development in the future. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Recommanded Product: 112656-95-8).

7-Nitroindoline-2,3-dione (cas: 112656-95-8) 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.Recommanded Product: 112656-95-8

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

Aryne approach towards 2,3-difluoro-10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles was written by Kopchuk, Dmitry S.;Nikonov, Igor L.;Zyryanov, Grigory V.;Nosova, Emiliya V.;Kovalev, Igor S.;Slepukhin, Pavel A.;Rusinov, Vladimir L.;Chupakhin, Oleg N.. And the article was included in Mendeleev Communications in 2015.Application of 774-47-0 This article mentions the following:

Reaction between 3-(2-pyridyl)-1,2,4-triazines and in situ generated 4,5-difluorobenzyne in toluene affords 2,3-difluoro-10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles. The structure of one representative compound was confirmed by X-ray diffraction anal. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Application of 774-47-0).

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) 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.Application 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