100-200 | - Page 18 of 93 - Indole Building Blocks

Romagnoli, Romeo et al. published their research in Letters in Drug Design & Discovery in 2009 | CAS: 167631-84-7

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) 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. 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: C10H8FNO2

Discovery of 8-methoxypyrazino[1,2-a]indole as a new potent antiproliferative agent against human leukemia K562 cells. a structure-activity relationship study was written by Romagnoli, Romeo;Baraldi, Pier Giovanni;Carrion, Maria Dora;Cruz-Lopez, Olga;Cara, Carlota Lopez;Preti, Delia;Tabrizi, Mojgan Aghazadeh;Balzarini, Jan;Hamel, Ernest;Fabbri, Enrica;Gambari, Roberto. And the article was included in Letters in Drug Design & Discovery in 2009.Formula: C10H8FNO2 This article mentions the following:

Identification of novel and selective anticancer agents remains an important and challenging goal in pharmacol. research. The indole nucleus, frequently encountered as a mol. fragment in natural products and pharmaceutically active compounds, was employed as the initial building block for the synthesis of a series of pyrazino[1,2-a]indoles 1a-k, variably substituted at the 6, 7, 8 and 9-positions. Compound 1e (I), bearing the methoxy group at the 8-position of the pyrazino[1,2-a]indole nucleus was identified as a novel potent antiproliferative agent against the human chronic myelogenous leukemia K562 cell line, but it was much less active against several other cancer cell lines. Comparison of positional isomers indicated that moving the methoxy group from the 8- to the 7- or 6-position, to furnish compounds 1f and 1g, resp., yielded inactive compounds The anal. of structure-activity relationships observed in the series of investigated compounds may represent the basis for the design of more active mols. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Formula: C10H8FNO2).

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

Kilic-Kurt, Zuehal et al. published their research in Archiv der Pharmazie (Weinheim, Germany) in 2020 | CAS: 167631-84-7

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) 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.Product Details of 167631-84-7

Novel indole hydrazide derivatives: Synthesis and their antiproliferative activities through inducing apoptosis and DNA damage was written by Kilic-Kurt, Zuehal;Acar, Cemre;Ergul, Mustafa;Bakar-Ates, Filiz;Altuntas, Tunca G.. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2020.Product Details of 167631-84-7 This article mentions the following:

A series of novel indole hydrazide derivatives was synthesized and evaluated for their anticancer activities. Compound 12(I) exhibited the highest antiproliferative activity against the MCF-7 cell line, with an IC₅₀ value of 3.01μM. Treatment of MCF-7 cells with compound 12 led to cell cycle arrest at the G0/G1 phase and also displayed a significant annexin V binding pattern, indicating that compound 12 is effective in apoptotic cell death. The Western blot anal. showed that compound 12 increased the expression of proapoptotic Bax and decreased the levels of the antiapoptotic Bcl-2 protein. It was also observed that MCF-7 cells treated with compound 12 showed reduced levels of procaspase-3 and -9 proteins. Moreover, compound 12 treatment induced a significant DNA damage in MCF-7 cells by increasing H2AX and ATM phosphorylation. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Product Details of 167631-84-7).

Nirwan, Narendra et al. published their research in Indian Journal of Heterocyclic Chemistry in 2018 | 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. 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.COA of Formula: C9H6ClNO

An efficient green synthesis of substituted indolylimidazole derivatives by employing reusable catalyst under microwave irradiation was written by Nirwan, Narendra;Pareek, Chandresh;Swami, V. K.. And the article was included in Indian Journal of Heterocyclic Chemistry in 2018.COA of Formula: C9H6ClNO This article mentions the following:

A simple highly versatile, green, and efficient one-pot synthesis of highly substituted indolylimidazole derivative I [R = H, Br, Cl, I; Ar = H, C₆H₅, 4-H₃CC₆H₄, 4-H₃COC₆H₄, 4-H₃CH₂COC₆H₄] is achieved by multicomponent condensation of benzil, indole-3-carbaldehydes II, ammonium acetate, and aromatic amines under microwave irradiation using Amberlyst A-15 as a reusable catalyst. This process has features of eco-friendly, very shorter reaction time, cost effectiveness and reusability of catalyst, easy workup, and purification of product with excellent yields. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0COA of Formula: C9H6ClNO).

Wang, Li Ming et al. published their research in Chirality in 2018 | CAS: 774-47-0

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Formula: C8H3F2NO2

Urea derivative catalyzed enantioselective aldol reaction of isatins with ketones was written by Wang, Li Ming;Zhao, Mei Jun;Chen, Zhe;Mu, Hong Wen;Jin, Ying. And the article was included in Chirality in 2018.Formula: C8H3F2NO2 This article mentions the following:

An efficient method was developed for the synthesis of 3-alkyl-3-hydroxyindolin-2-ones I (R¹ = H, 5-Me, 7-F, etc.; R² = Me, Ph, 4-ClC₆H₄) via chiral urea-catalyzed asym. aldol reaction of isatins with ketones R²C(O)Me. The resulting products I were obtained in good yields (70%-94%) with high enantioselectivities (up to 87% ee). In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Formula: C8H3F2NO2).

Sharma, Saurabh et al. published their research in New Journal of Chemistry in 2019 | CAS: 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.Recommanded Product: 4769-96-4

Hydrogenation of nitroarenes to anilines in a flow reactor using polystyrene supported rhodium in a catalyst-cartridge (Cart-Rh@PS) was written by Sharma, Saurabh;Yamini;Das, Pralay. And the article was included in New Journal of Chemistry in 2019.Recommanded Product: 4769-96-4 This article mentions the following:

The present methodol. described the chemo-selective hydrogenation of various nitroarenes in a flow reactor under polystyrene supported rhodium in a catalyst-cartridge (Cart-Rh@PS) as a heterogeneous nano-catalyst. The polystyrene supported Rh (Rh@PS) nanoparticles (NPs) were prepared by following our earlier reported protocol and packed inside the catalyst-cartridge (Cat-Cart) to obtain Cart-Rh@PS, which is compatible with ThalesNano’s H-Cube Pro flow system. The advantages of the prepacked catalyst Cart-Rh@PS are as follows: no need for catalyst activation up to 12 runs, negligible metal leaching detected by ICP-AES anal. and significantly less back pressure generated under the flow conditions. The same catalyst, Cart-Rh@PS, was also effective up to a 1 g scale for the reduction of nitroarenes and reusable for successive runs. The hydrogenation in the flow reactor is a greener approach for the reduction of nitroarenes to their corresponding anilines in high yields. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Recommanded Product: 4769-96-4).

Kamila, Sukanta et al. published their research in Open Organic Chemistry Journal in 2011 | 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 5-Chloroindole-3-carboxaldehyde

Synthesis of novel pyridobenzimidazoles bonded to indole or benzo[b]thiophene structures was written by Kamila, Sukanta;Ankati, Haribabu;Mendoza, Kimberly;Biehl, Edward R.. And the article was included in Open Organic Chemistry Journal in 2011.Recommanded Product: 5-Chloroindole-3-carboxaldehyde This article mentions the following:

Pyridobenzimidazoles I (R¹ = R² = R³ = H, X = NH, Y = CH; R¹ = MeO, R² = R³ = H, X = NH, Y = N; R¹ = R, R² = R³ = H, X = S, Y = CH; etc.) were synthesized in very good to excellent yields (81-96 %) by the condensation of substituted N-phenyl-o-phenylenediamines with indole/benzo[b]thiophene-3-aldehydes 5a-t in methoxyethanol under reflux conditions. The diamines were prepared by first treating 2-chloro-3-nitropyridine with suitably substituted anilines, then reducing the resulting 3-nitro-N-phenylpyridin-2-amines with tin(II)chloride using microwave heating in each case. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Recommanded Product: 5-Chloroindole-3-carboxaldehyde).

Zhang, Huiming et al. published their research in Youji Huaxue in 2014 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) 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.Product Details of 4769-96-4

Synthesis of 3-indolyl-substituted benzoboroxole via Friedel-Crafts reaction in water was written by Zhang, Huiming;Shen, Shaochun;Yang, Xiaodi;Sun, Xingwen. And the article was included in Youji Huaxue in 2014.Product Details of 4769-96-4 This article mentions the following:

A highly efficient and catalyst free approach for the synthesis of 3-indolyl-substituted benzoboroxole via Friedel-Crafts reaction in water was developed successfully using readily accessible 2-formylbenzeneboronic acid and indole as the starting material and water as solvent at room temperature An array of desired 3-indolyl-substituted benzoboroxoles was synthesized in moderate to near quant. yield. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Product Details of 4769-96-4).

Rani, B. Shoba et al. published their research in World Journal of Pharmacy and Pharmaceutical Sciences in 2016 | 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. 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). HPLC of Formula: 112656-95-8

Cytotoxic, antioxidant and anti-inflammatory activity of N-(6-benzoyl-1H-benzo [d]imidazol-2-yl)-2-(2-oxosubtituted indolin-3-ylidene) hydrazine carboxamides was written by Rani, B. Shoba;Priyanka, K. Blessi;Harikiran, L.;Sammaiah, G.. And the article was included in World Journal of Pharmacy and Pharmaceutical Sciences in 2016.HPLC of Formula: 112656-95-8 This article mentions the following:

In the present study novel series of N-(6-benzoyl-1H-benzo[d]imidazol-2-yl)-2-(2-oxosubstitutedindolin-3-ylidene) hydrazine carboxamides (III a-m) have been synthesized in good yields and characterized by IR, NMR and mass spectral analyses. The compounds were evaluated for their preliminary in vitro cytotoxic activity against HCT-116 (colon ) and HepG2 (hepatocellular) cancer cell lines by standard MTT assay, antioxidant activity by standard DPPH assay method and also were screened for in vitro anti-inflammatory activity by TMPD assay method. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8HPLC of Formula: 112656-95-8).

Liddle, John et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2021 | CAS: 90322-37-5

2-Oxoindoline-4-carboxylic acid (cas: 90322-37-5) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Synthetic Route of C9H7NO3

The development of highly potent and selective small molecule correctors of Z α₁-antitrypsin misfolding was written by Liddle, John;Pearce, Andrew C.;Arico-Muendel, Christopher;Belyanskaya, Svetlana;Brewster, Andrew;Brown, Murray;Chung, Chun-wa;Denis, Alexis;Dodic, Nerina;Dossang, Anthony;Eddershaw, Peter;Klimaszewska, Diana;Haq, Imran;Holmes, Duncan S.;Jagger, Alistair;Jakhria, Toral;Jigorel, Emilie;Lind, Ken;Messer, Jeff;Neu, Margaret;Olszewski, Allison;Ronzoni, Riccardo;Rowedder, James;Rudiger, Martin;Skinner, Steve;Smith, Kathrine J.;Trottet, Lionel;Uings, Iain;Zhu, Zhengrong;Irving, James A.;Lomas, David A.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2021.Synthetic Route of C9H7NO3 This article mentions the following:

α1-Antitrypsin deficiency is characterized by the misfolding and intracellular polymerization of mutant α1-antitrypsin protein within the endoplasmic reticulum (ER) of hepatocytes. Small mols. that bind and stabilize Z α₁-antitrypsin were identified via a DNA-encoded library screen. A subsequent structure-based optimization led to a series of highly potent, selective and cellular active α1-antitrypsin correctors, e.g., I. In the experiment, the researchers used many compounds, for example, 2-Oxoindoline-4-carboxylic acid (cas: 90322-37-5Synthetic Route of C9H7NO3).

Saint-Louis, Carl Jacky et al. published their research in Organic & Biomolecular Chemistry in 2017 | CAS: 110568-64-4

6-Nitroisoindolin-1-one (cas: 110568-64-4) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.COA of Formula: C8H6N2O3

Synthesis, computational, and spectroscopic analysis of tunable highly fluorescent BN-1,2-azaborine derivatives containing the N-BOH moiety was written by Saint-Louis, Carl Jacky;Shavnore, Renee N.;McClinton, Caleb D. C.;Wilson, Julie A.;Magill, Lacey L.;Brown, Breanna M.;Lamb, Robert W.;Webster, Charles Edwin;Schrock, Alan K.;Huggins, Michael T.. And the article was included in Organic & Biomolecular Chemistry in 2017.COA of Formula: C8H6N2O3 This article mentions the following:

Nine new polycyclic aromatic BN-1,2-azaborine analogs containing the N-BOH moiety were synthesized using a convenient two-step, one-pot procedure. Characterization of the prepared compounds show the luminescence wavelength and the quantum yields of the azaborines were tunable by controlling the power and location of the donor and acceptor substituents on the chromophore. UV-visible spectroscopy and d. functional theory (DFT) computations revealed that the addition of electron-donating moieties to the isoindolinone hemisphere raised the energy of the HOMO, resulting in the reduction of the HOMO-LUMO gap. The addition of an electron-accepting moiety to the isoindolinone hemisphere and an electron-donating group to the boronic acid hemisphere decreased the HOMO-LUMO gap considerably, leading to emission properties from partial intramol. charge transfer (ICT) states. The combined effect of an acceptor on the isoindolinone side and a donor on the boronic acid side (strong acceptor-π-donor) gave the most red-shifted absorption. The polycyclic aromatic BN-1,2-azaborines emitted strong fluorescence in solution and in the solid-state with the largest red-shifted emission at 640 nm and a Stokes shift of Δλ = 218 nm, or Δν = 8070 cm^-1. In the experiment, the researchers used many compounds, for example, 6-Nitroisoindolin-1-one (cas: 110568-64-4COA of Formula: C8H6N2O3).