indole-building-block | - Page 75 of 1434

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).

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

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).

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).

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).

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).

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).

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).

Zaryanova, Ekaterina V. et al. published their research in Tetrahedron in 2017 | CAS: 112656-95-8

7-Nitroindoline-2,3-dione (cas: 112656-95-8) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Application In Synthesis of 7-Nitroindoline-2,3-dione

Synthesis and reactivity of new amide-substituted oxindole derivatives was written by Zaryanova, Ekaterina V.;Ignatov, Alexander A.;Lozynskaya, Nataly A.. And the article was included in Tetrahedron in 2017.Application In Synthesis of 7-Nitroindoline-2,3-dione This article mentions the following:

A general approach to the synthesis of oxindole-based amides I (R = 5-NHC(O)OMe, 5-NHCOPh, 5-NHCOPh-7-NHCOMe, etc.) is described. To stabilize the aminoisatin mol. for further modifications, the carbonyl group in the 3-position of the starting nitroisatins was protected by conversion into a ketal. Next, the reduction of the nitro group and further acylation of the resulting amino group were carried out to provide the corresponding mono- and diamido-substituted isatins I. The possibility of their modification in the 3-position for the synthesis of potent biol. active compounds is demonstrated. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Application In Synthesis of 7-Nitroindoline-2,3-dione).

Penthala, Narsimha Reddy et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2010 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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. 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.Formula: C9H6ClNO

Microwave assisted synthesis and in vitro cytotoxicities of substituted (Z)-2-amino-5-(1-benzyl-1H-indol-3-yl)methylene-1-methyl-1H-imidazol-4(5H)-ones against human tumor cell lines was written by Penthala, Narsimha Reddy;Yerramreddy, Thirupathi Reddy;Crooks, Peter A.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2010.Formula: C9H6ClNO This article mentions the following:

The synthesis of several novel substituted (Z)-2-amino-5-(1-benzyl-1H-indol-3-yl)methylene-1-methyl-1H-imidazol-4(5H)-ones structurally related to aplysinopsin have been carried out under microwave irradiation and conventional heating methods. Several of these compounds were evaluated for their in vitro cytotoxic activity against an NCI 60 human tumor cell line panel. Compound 3f exhibited good growth inhibitory properties against all but four of the human cancer cell lines examined, and afforded LC₅₀ values <10 濠电偞鎸鹃幏?for 30% of the cell lines in the panel. Compound 3e was an effective inhibitor of leukemia, CNS, melanoma, and breast cancer cell growth, but generally less effective as a cytotoxic agent. Thus, the aplysinopsin analog 3f was regarded as a useful lead compound for further structural optimization. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Formula: C9H6ClNO).

Paintner, Franz F. et al. published their research in Synlett in 2002 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. 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 2-(Phenylthio)isoindoline-1,3-dione

Synthetic studies toward tetrodecamycin: an efficient approach to the core structure of the antibiotic was written by Paintner, Franz F.;Allmendinger, Lars;Bauschke, Gerd;Polborn, Kurt. And the article was included in Synlett in 2002.Application In Synthesis of 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:

An efficient synthetic pathway to the core structure I of the polyketide antibiotic tetrodecamycin has been developed. Our approach features the acid-catalyzed cyclization of a tert-butyldimethylsilyl protected Me 婵?(缂?hydroxyacyl) tetronate, leading to the novel tricyclic ring skeleton exhibited by I. An insight into the mechanism of this key ring closure step has been gained. Furthermore an alternative pathway to this ring skeleton, based on a fluoride ion induced desilylation-cyclization sequence, has been disclosed. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Application In Synthesis of 2-(Phenylthio)isoindoline-1,3-dione).