February 2023 - Page 111 of 117 - Indole Building Blocks

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).

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

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).

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).

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).

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).

Singha Roy, Soumya Jyoti et al. published their research in Organic & Biomolecular Chemistry in 2017 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Computed Properties of C14H9NO2S

“On water” catalytic enantioselective sulfenylation of deconjugated butyrolactams was written by Singha Roy, Soumya Jyoti;Mukherjee, Santanu. And the article was included in Organic & Biomolecular Chemistry in 2017.Computed Properties of C14H9NO2S This article mentions the following:

In the presence of phthalazine-linked quinidine or quinine dimers, deconjugated γ-butenolactams such as racemic I (R = H) underwent enantioselective arylsulfenylation and phenylselenenylation reactions with arylthio- and phenylselenosuccinimides in tert-butylbenzene/water mixtures to yield nonracemic α-arylthio- and α-phenylselenenobutenolactams such as I (R = PhS, PhSe) in 56-94% yields and in 47->96% ee; a lactam with an α-iso-Pr substituent and benzylthiol- and cyclohexanethiol-derived succinimides did not yield sulfenylation products. Oxidation and rearrangement of I (R = PhSe) yielded a nonracemic γ-hydroxybutenolactam by formal γ-hydroxylation; the selenylation and hydroxylation reactions were performed in tandem. The structures of I (R = PhS, PhSe) and of the oxidation and rearrangement product of I (R = PhSe) were determined by X-ray crystallog. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Computed Properties of C14H9NO2S).

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).

Song, Jiahui et al. published their research in Asian Journal of Organic Chemistry in 2013 | CAS: 1256359-99-5

tert-Butyl 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (cas: 1256359-99-5) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Computed Properties of C20H28BNO5

Copper-Catalyzed N-Alkynylation of N-tert-Butoxycarbonyl (BOC)-Protected Indoles was written by Song, Jiahui;Wang, Qingbo;Fu, Haixing;Fu, Songlin;Li, Shaobin;Shi, Feng;Wu, Chunrui. And the article was included in Asian Journal of Organic Chemistry in 2013.Computed Properties of C20H28BNO5 This article mentions the following:

N-BOC-indole derivatives undergo a copper-catalyzed N-alkynylation with alkynyl bromides after in situ deprotection. Potassium tert-butoxide was used for the deprotection of substrates and as a base during the cross-coupling stage. For substrates that contain a 2-pyridine group or similar group, a phenanthroline ligand was not needed. This serves as an alternative protocol for N-alkynylation of indoles with a broader scope of substrates. The title compounds thus formed included an (ethynyl)indole derivative (I) and related substances. The synthesis of the target compounds was achieved using 3-(2-pyridinyl)-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester, 5-(2-pyridinyl)-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester, 1H-Indole-1,2-dicarboxylic acid 1,2-bis(1,1-dimethylethyl) ester, 4-cyano-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester, etc., as starting materials in a reaction with bromoalkyne derivatives A similar reaction of 1H-benzimidazole-1-carboxylic acid 1,1-dimethylethyl ester gave 1-(2-phenylethynyl)-1H-benzimidazole. A reaction of 1H-pyrrole-1-carboxylic acid 1,1-dimethylethyl ester derivatives gave 1-(2-phenylethynyl)-1H-pyrrole derivatives In the experiment, the researchers used many compounds, for example, tert-Butyl 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (cas: 1256359-99-5Computed Properties of C20H28BNO5).

Pratihar, Sanjay et al. published their research in Organic & Biomolecular Chemistry in 2014 | 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Quality Control of 5-Chloroindole-3-carboxaldehyde

Electrophilicity and nucleophilicity of commonly used aldehydes was written by Pratihar, Sanjay. And the article was included in Organic & Biomolecular Chemistry in 2014.Quality Control of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

The present approach for determining the electrophilicity (E) and nucleophilicity (N) of aldehydes includes a kinetic study of KMNO₄ oxidation and NaBH₄ reduction of aldehydes. A transition state anal. of the KMNO₄ promoted aldehyde oxidation reaction has been performed, which shows a very good correlation with exptl. results. The validity of the exptl. method has been tested using the exptl. activation parameters of the two reactions. The utility of the present approach is further demonstrated by the theor. vs. exptl. relationship, which provides easy access to E and N values for various aldehydes and offers an at-a-glance assessment of the chem. reactivity of aldehydes in various reactions. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Quality Control of 5-Chloroindole-3-carboxaldehyde).

Li, Xiang et al. published their research in ACS Catalysis in 2014 | CAS: 170489-16-4

1,4-Dimethyl-1H-indole-3-carbaldehyde (cas: 170489-16-4) 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 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 of 170489-16-4

Aerobic Transition-Metal-Free Visible-Light Photoredox Indole C-3 Formylation Reaction was written by Li, Xiang;Gu, Xiangyong;Li, Yongjuan;Li, Pixu. And the article was included in ACS Catalysis in 2014.Application of 170489-16-4 This article mentions the following:

An aerobic visible-light-promoted indole C-3 formylation reaction catalyzed by Rose Bengal has been developed. This transition-metal-free process employs mol. oxygen as the terminal oxidant and uses TMEDA as the one-carbon source through C-N bond cleavage. The reaction is compatible with a variety of functional groups. In the experiment, the researchers used many compounds, for example, 1,4-Dimethyl-1H-indole-3-carbaldehyde (cas: 170489-16-4Application of 170489-16-4).