20/02/2023 - Page 2 of 14 - Indole Building Blocks

Waaler, Jo et al. published their research in Journal of Medicinal Chemistry in 2020 | CAS: 898746-35-5

1H-Pyrrolo[2,3-b]pyridine-6-carboxylic acid (cas: 898746-35-5) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.HPLC of Formula: 898746-35-5

Preclinical Lead Optimization of a 1,2,4-Triazole Based Tankyrase Inhibitor was written by Waaler, Jo;Leenders, Ruben G. G.;Sowa, Sven T.;Alam Brinch, Shoshy;Lycke, Max;Nieczypor, Piotr;Aertssen, Sjoerd;Murthy, Sudarshan;Galera-Prat, Albert;Damen, Eddy;Wegert, Anita;Nazare, Marc;Lehtio, Lari;Krauss, Stefan. And the article was included in Journal of Medicinal Chemistry in 2020.HPLC of Formula: 898746-35-5 This article mentions the following:

Tankyrases 1 and 2 are central biotargets in the WNT/闁?catenin signaling and Hippo signaling pathways. We have previously developed tankyrase inhibitors bearing a 1,2,4-triazole moiety and binding predominantly to the adenosine binding site of the tankyrase catalytic domain. Here we describe a systematic structure-guided lead optimization approach of these tankyrase inhibitors. The central 1,2,4-triazole template and trans-cyclobutyl linker of the lead compound 1 (I) were left unchanged, while side-group East, West, and South moieties were altered by introducing different building blocks defined as point mutations. The systematic study provided a novel series of compounds reaching picomolar IC₅₀ inhibition in WNT/闁?catenin signaling cellular reporter assay. The novel optimized lead 13 (II) resolves previous atropisomerism, solubility, and Caco-2 efflux liabilities. 13 Shows a favorable ADME profile, including improved Caco-2 permeability and oral bioavailability in mice, and exhibits antiproliferative efficacy in the colon cancer cell line COLO 320DM in vitro. In the experiment, the researchers used many compounds, for example, 1H-Pyrrolo[2,3-b]pyridine-6-carboxylic acid (cas: 898746-35-5HPLC of Formula: 898746-35-5).

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

Monakhova, Natalia et al. published their research in ACS Infectious Diseases in 2021 | 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Product Details of 827-01-0

Design and synthesis of pyrano[3,2-b]indolones showing antimycobacterial activity was written by Monakhova, Natalia;Kordulakova, Jana;Vocat, Anthony;Egorova, Anna;Lepioshkin, Alexander;Salina, Elena G.;Nosek, Jozef;Repkova, Eva;Zemanova, Julia;Jurdakova, Helena;Gorova, Renata;Roh, Jaroslav;Degiacomi, Giulia;Sammartino, Jose Camilla;Pasca, Maria Rosalia;Cole, Stewart T.;Mikusova, Katarina;Makarov, Vadim. And the article was included in ACS Infectious Diseases in 2021.Product Details of 827-01-0 This article mentions the following:

Latent Mycobacterium tuberculosis infection presents one of the largest challenges for tuberculosis control and novel antimycobacterial drug development. A series of pyrano[3,2-b]indolone-based compounds was designed and synthesized via an original eight-step scheme. The synthesized compounds were evaluated for their in vitro activity against M. tuberculosis strains H37Rv and streptomycin-starved 18b (SS18b), representing models for replicating and nonreplicating mycobacteria, resp. Some of compound exhibited good activity with MIC₉₉ values of 0.3 and 0.4濠电偞鎸鹃幐?mL against H37Rv and SS18b, resp., as well as low toxicity, acceptable intracellular activity, and satisfactory metabolic stability and was selected as the lead compound for further studies. An anal. of 10a-resistant M. bovis mutants disclosed a cross-resistance with pretomanid and altered relative amounts of different forms of cofactor F₄₂₀ in these strains. Complementation experiments showed that F₄₂₀-dependent glucose-6-phosphate dehydrogenase and the synthesis of mature F₄₂₀ were important for 10a activity. Overall these studies revealed 10a to be a prodrug that is activated by an unknown F₄₂₀-dependent enzyme in mycobacteria. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Product Details of 827-01-0).

Noland, Wayland E. et al. published their research in Journal of Organic Chemistry in 1965 | CAS: 3484-23-9

2-Methyl-6-nitro-1H-indole (cas: 3484-23-9) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Formula: C9H8N2O2

Nitration of indoles. III. Polynitration of 2-alkylindoles was written by Noland, Wayland E.;Smith, Lowell R.;Rush, Kent R.. And the article was included in Journal of Organic Chemistry in 1965.Formula: C9H8N2O2 This article mentions the following:

Nitration in concentrated nitric acid of 2-methylindole and 1,2-dimethylindole gives the corresponding 3,6-dinitroindoles I and II; I was also obtained from 2-methylindole-3-carboxaldehyde and 2-methyl-6-nitroindole. 2-Methyl-3-nitroindole and 2-methyl-3H-indol-3-one oxime gives both I and 3,4-dinitro-2-methylindole (III); III was also obtained from 2-methyl-4-nitroindole (IV). Further nitration of I and II or their precursors gives the corresponding 3,4,6-trinitroindoles V and VI; 3-acetyl-2-methyl-4-nitroindole and IV also gave V. Nitration in concentrated nitric acid of 2-methyl-5-nitroindole (VI) and 1,2-dimethyl-5-nitroindole (VII) gives the corresponding 3,5-dinitroindoles VIII and IX. Further nitration of VIII and IX (or VII) gives the 3,5,6-trinitroindoles X and XI; X was also obtained from the 1-acetyl derivative or VI. Dimethylation of VIII gave 3,5-dinitro-2-ethyl-1-methylindole (XII), as proved by preparation from 2-ethylindole via the 5-nitro and 3,5-dinitro derivatives and methylation to XII. Nitration in concentrated sulfuric acid of 1,2,3-trimethylindole and 2,3,3-trimethyl-3H-indole gives the corresponding 5-nitro derivatives. The differing mechanisms of nitration of indoles in sulfuric acid and in nitric or acetic acids are discussed, and a set of orientation rules for nitration of 2-alkylindoles is presented. In the experiment, the researchers used many compounds, for example, 2-Methyl-6-nitro-1H-indole (cas: 3484-23-9Formula: C9H8N2O2).

Wu, Yinrong et al. published their research in Organic Letters in 2021 | CAS: 89245-41-0

4-Bromoindole-3-acetic Acid (cas: 89245-41-0) 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.Application of 89245-41-0

Copper-Mediated Decarboxylative Coupling between Arylacetic Acids and 1,3-Dicarbonyl Compounds was written by Wu, Yinrong;Wen, Kangmei;Chen, Jiewen;Shi, Jie;Yao, Xingang;Tang, Xiaodong. And the article was included in Organic Letters in 2021.Application of 89245-41-0 This article mentions the following:

A copper-mediated decarboxylative coupling reaction between arylacetic acids and 1,3-dicarbonyl compounds was described for the synthesis of ((indolyl)methyl)-oxocycloalkyl-esters, e.g., I. Significantly, methanocycloocta[b]indoles II [R = COOEt, CONHEt, SO₂Ph, etc.; R¹ = H, 4-Cl, 5-Br, etc.] were also obtained by sequential intramol. dehydrocyclization process in some cases. This protocol featured a broad substrate scope, simple operations, and good yields. Moreover, the products exhibited potent antiproliferative activity against the human cancer cell lines by a MTT assay. In the experiment, the researchers used many compounds, for example, 4-Bromoindole-3-acetic Acid (cas: 89245-41-0Application of 89245-41-0).

Yang, Ze-ren et al. published their research in Chemical Communications (Cambridge, United Kingdom) in 2022 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Application In Synthesis of 6-Nitro-1H-indole

Palladium-catalyzed hydroamination of vinylidenecyclopropane-diester with pyrroles and indoles: an approach to azaaromatic vinylcyclopropanes was written by Yang, Ze-ren;Zhang, Bo;Long, Yong-jie;Shi, Min. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2022.Application In Synthesis of 6-Nitro-1H-indole This article mentions the following:

A new method for the synthesis of azaarom. vinylcyclopropanes (VCPs) was disclosed in this paper by using pyrrole or indole derivatives as nucleophilic reagents to react with vinylidenecyclopropane-diesters (VDCP-diesters) in the presence of a Pd catalyst, a phosphine ligand and a base under mild conditions in up to 98% yield with a reasonable substrate scope. This reaction was one of the few examples of hydroamination at electron-rich allene’s 闁?position. A plausible reaction mechanism has also been proposed through a zwitterionic 闂?propargyl N-palladium species according to the previous work and the obtained deuterium labeling exptl. result. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Application In Synthesis of 6-Nitro-1H-indole).

Hulpia, Fabian et al. published their research in ACS Infectious Diseases in 2020 | CAS: 1000340-39-5

3-Bromo-4-chloro-7-azaindole (cas: 1000340-39-5) 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.Recommanded Product: 1000340-39-5

Structure-Activity Relationship Exploration of 3′-Deoxy-7-deazapurine Nucleoside Analogues as Anti-Trypanosoma brucei Agents was written by Hulpia, Fabian;Campagnaro, Gustavo D.;Alzahrani, Khalid J.;Alfayez, Ibrahim A.;Ungogo, Marzuq A.;Mabille, Dorien;Maes, Louis;de Koning, Harry P.;Caljon, Guy;Van Calenbergh, Serge. And the article was included in ACS Infectious Diseases in 2020.Recommanded Product: 1000340-39-5 This article mentions the following:

Human African trypanosomiasis is a neglected tropical disease caused by Trypanosoma brucei parasites. These protists are unable to produce the purine ring, making them vulnerable to the effects of purine nucleoside analogs. Starting from 3′-deoxytubercidin (5), a lead compound with activity against central-nervous-stage human African trypanosomiasis, we investigate the structure-activity relationships of the purine and ribofuranose rings. The purine ring tolerated only modifications at C7, while from the many alterations of the 3′-deoxyribofuranosyl moiety only the arabino analog 48 showed pronounced antitrypanosomal activity. Profiling of the most potent analogs against resistant T. brucei strains (resistant to pentamidine, diminazene, and isometamidium) showed reduced dependence on uptake mediated by the P2 aminopurine transporter relative to 5. The introduction of a 7-substituent confers up to 10-fold increased affinity for the P1 nucleoside transporter while generally retaining high affinity for P2. Four of the most promising analogs were found to be metabolically stable, earmarking them as suitable backup analogs for lead 5. In the experiment, the researchers used many compounds, for example, 3-Bromo-4-chloro-7-azaindole (cas: 1000340-39-5Recommanded Product: 1000340-39-5).

Karadayi, Fikriye Zengin et al. published their research in Bioorganic Chemistry in 2020 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.COA of Formula: C9H6ClNO

Design, synthesis and anticancer/antiestrogenic activities of novel indole-benzimidazoles was written by Karadayi, Fikriye Zengin;Yaman, Murat;Kisla, Mehmet Murat;Keskus, Ayse G.;Konu, Ozlen;Ates-Alagoz, Zeynep. And the article was included in Bioorganic Chemistry in 2020.COA of Formula: C9H6ClNO This article mentions the following:

In this study, a novel ethylsulfonyl indole-benzimidazole derivatives I [R¹ = H, Me, cyclohexyl, etc.; R² = H, MeO, Cl, Br] were synthesized. Subsequently, ¹H NMR, ¹³C NMR, and Mass spectral and in silico docking analyses, and anticancer activity screening studies of these novel indole-benzimidazoles were performed. The antiproliferative effects of indole-benzimidazoles I were found to be more similar between the estrogen (E2) responsive cell lines MCF-7 and HEPG2 in comparison to the Estrogen Receptor neg. (ER^–) cell line MDA-MB-231. Microarray expression profiling and gene enrichment analyses (GSEA) of the selected compounds I [R¹ = 4-fluorobenzyl, R² = H, MeO, Cl, Br; R¹ = 3,4-difluorobenzyl, R² = MeO] helped determine the similarly modulated cellular signaling pathways among derivatives Moreover, some known compounds were identified that had significantly similar gene signatures to that of I [R¹ = 4-fluorobenzyl; R² = Br] via queries performed in LINCS database; and further transcriptomics comparisons were made using public GEO datasets (GSE35428, GSE7765, GSE62673). Results strongly demonstrated that these novel indole-benzimidazoles can modulate ER target gene expression as well as dioxin-mediated aryl hydrocarbon receptor and amino acid deprivation-mediated integrated stress response signaling in a dose-dependent manner. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0COA of Formula: C9H6ClNO).

Kopchuk, Dmitry S. et al. published their research in Organic & Biomolecular Chemistry in 2018 | CAS: 774-47-0

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.COA of Formula: C8H3F2NO2

Studies on the interactions of 5-R-3-(2-pyridyl)-1,2,4-triazines with arynes: inverse demand aza-Diels-Alder reaction versus aryne-mediated domino process was written by Kopchuk, Dmitry S.;Nikonov, Igor L.;Khasanov, Albert F.;Giri, Kousik;Santra, Sougata;Kovalev, Igor S.;Nosova, Emiliya V.;Gundala, Sravya;Venkatapuram, Padmavathi;Zyryanov, Grigory V.;Majee, Adinath;Chupakhin, Oleg N.. And the article was included in Organic & Biomolecular Chemistry in 2018.COA of Formula: C8H3F2NO2 This article mentions the following:

The interactions between substituted 5-substituted-3-(2-pyridyl)-1,2,4-triazines I [R¹ = H, Ph, indol-3-yl, etc. ; R² = Ph, 4-BrC₆H₄, 4-O₂NC₆H₄, etc.] with in-situ generated substituted aryne intermediates were studied. The reaction afforded either inverse demand (ID) aza-Diels-Alder products or 1,2,4-triazine ring rearrangement (domino) products as major ones depending on the nature of both the substituents at the C5 position of the 1,2,4-triazine core or in the aryne moiety. The structures of the key products were confirmed based on X-ray data. Based on the d. functional theor. (DFT) studies of the Diels-Alder transition state geometries, the influence of the nature of arynes on the direction of the 1,2,4-triazine transformation were proposed. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0COA of Formula: C8H3F2NO2).

Bhat, Radhika et al. published their research in Nucleosides, Nucleotides & Nucleic Acids in 2021 | 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Recommanded Product: 827-01-0

Synthesis, characterization and molecular docking studies of new indol(1H-3-yl)pyrimidine derivatives: Insights into their role in DNA interaction was written by Bhat, Radhika;Begum, Noor Shahina. And the article was included in Nucleosides, Nucleotides & Nucleic Acids in 2021.Recommanded Product: 827-01-0 This article mentions the following:

This study reports the synthesis of new indol(1H-3-yl) pyrimidine derivatives using various substituted indole-3-carbaldehydes, urea and malononitrile in the presence of ammonium chloride. The resulting compounds were characterized using anal. and spectroscopic methods. The mol. docking study exhibits that among the synthesized compounds, have great binding ability toward B-DNA. The binding efficiencies of compounds with CT-DNA were evaluated via UV-visible absorption spectral and viscosity studies. The findings establish that the compounds firmly bind through an intercalative mode to CT-DNA and provide a unique pattern of DNA binding. The photo-induced cleavage indicates that the compounds have UV-visible photo nuclease properties toward plasmid DNA as revealed by agarose gel electrophoresis approach. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Recommanded Product: 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Recommanded Product: 827-01-0

Betterley, Nolan M. et al. published their research in Asian Journal of Organic Chemistry in 2018 | 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. 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.Quality Control of 5-Chloroindole-3-carboxaldehyde

Bi(OTf)₃ Enabled C-F Bond Cleavage in HFIP: Electrophilic Aromatic Formylation with Difluoro(phenylsulfanyl)methane was written by Betterley, Nolan M.;Kerdphon, Sutthichat;Chaturonrutsamee, Suppisak;Kongsriprapan, Sopanat;Surawatanawong, Panida;Soorukram, Darunee;Pohmakotr, Manat;Andersson, Pher G.;Reutrakul, Vichai;Kuhakarn, Chutima. And the article was included in Asian Journal of Organic Chemistry in 2018.Quality Control of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

Bismuth(III) trifluoromethanesulfonate [Bi(OTf)₃] mediated mild electrophilic aromatic formylation utilizing difluoro(phenylsulfanyl)methane (PhSCF₂H) as a formylating agent in hexafluoro-2-propanol (HFIP) as a recyclable ionizing solvent has been developed. The active formylating species was generated via C-F bond cleavage and was characterized to be a bis(phenylsulfanyl)methyl cation by exptl. and computational ¹H and ¹³C NMR. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Quality Control of 5-Chloroindole-3-carboxaldehyde).