100-200 | - Indole Building Blocks

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

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).

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).

Cheng, Guangsheng et al. published their research in European Journal of Organic Chemistry in 2017 | 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Computed Properties of C9H6ClNO

Isocyanide-Based Multicomponent Reaction To Furnish N-Functionalized Indoles by using N-Acyliminium Ions as Key Intermediates was written by Cheng, Guangsheng;Deng, Hongmei;He, Xiang;Gao, Yu;Li, Chunju;Jia, Xueshun;Li, Jian. And the article was included in European Journal of Organic Chemistry in 2017.Computed Properties of C9H6ClNO This article mentions the following:

The present work discloses an efficient multicomponent reaction of isocyanides, allenoates, and indoles. This protocol provides rapid and direct access to N-functionalized indoles from readily available starting materials, in the absence of any catalyst. The strategy also features a broad substrate scope and mild conditions. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Computed Properties of C9H6ClNO).

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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Computed Properties of C9H6ClNO

Beckett, Arnold H. et al. published their research in Tetrahedron in 1968 | CAS: 20870-91-1

5-Amino-1-methyl-2-oxoindoline (cas: 20870-91-1) 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.Reference of 20870-91-1

Substituted oxindoles. I. The preparation and spectral characteristics of some simple oxindole derivatives was written by Beckett, Arnold H.;Daisley, R. W.;Walker, J.. And the article was included in Tetrahedron in 1968.Reference of 20870-91-1 This article mentions the following:

A series of oxindole derivatives substituted in the aromatic ring and their 1-Me homologs was prepared The effects of position and nature of substituents on the ir, N.M.R. and uv spectra were investigated. Evidence is presented which indicates the presence of an intermol. H bond in solutions of oxindole and certain 1-substituted derivatives A relation between the Hammett 闂?constant of substituents and the carbonyl frequencies of these oxindoles is reported. In the experiment, the researchers used many compounds, for example, 5-Amino-1-methyl-2-oxoindoline (cas: 20870-91-1Reference of 20870-91-1).

Moseley, Jonathan D. et al. published their research in Tetrahedron in 2012 | 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Product Details of 827-01-0

A mild robust generic protocol for the Suzuki reaction using an air stable catalyst was written by Moseley, Jonathan D.;Murray, Paul M.;Turp, Edward R.;Tyler, Simon N. G.;Burn, Ross T.. And the article was included in Tetrahedron in 2012.Product Details of 827-01-0 This article mentions the following:

A mild but robust procedure was developed as a 1st pass generic protocol for the Suzuki-Miyaura reaction. The protocol employs an air stable Pd pre-catalyst at low loading (闂? mol%) in aqueous solvent mixtures at moderate temperature using K₂CO₃ as base. Under these mild conditions, most aryl bromides will react with sterically and electronically demanding arylboronates to give complete conversion to the product biphenyls in <1 h. Aryl chlorides are also fully converted in most cases either under identical conditions in 8-24 h, or in 2 h at elevated temperature A further advantage of these mild conditions of moderate temperature, weak base, and benign solvent is that sensitive functional groups and structural motifs are well tolerated. In addition, the lipophilic biphenyl products are readily isolated after a simple work-up procedure. These generic conditions are ideal for proof of transformation, and as the starting point for development and optimization of a specific process. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Product Details of 827-01-0).