20/02/2023 - Page 6 of 14 - Indole Building Blocks

Cao, Yun-yun et al. published their research in Zhongguo Yaowu Huaxue Zazhi in 2013 | 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Related Products of 774-47-0

Synthesis and antitumor activity of novel 6-substituted methylenehydrazinyl-2,4-bismorpholino-pyrimidine and 1,3,5-triazine derivatives was written by Cao, Yun-yun;Zhu, Wu-fu;Zhu, Yan;Guo, Fei;Lu, Xiang-ran;Gong, Ping. And the article was included in Zhongguo Yaowu Huaxue Zazhi in 2013.Related Products of 774-47-0 This article mentions the following:

A series of 6-substituted methylenehydrazinyl-2,4-bismorpholino-pyrimidine and 1,3,5-triazine derivatives were synthesized and their chem. structures were confirmed by ¹H-NMR and MS spectra. As the raw materials, 2,4,6-trichloropyrimidine or cyanuric chloride, aniline, benzimidazole and pyrrole were used to obtain the title compounds by multi-step reactions including substitution, cyclization, N-alkylation and Vilsmeier reaction. All the synthesized compounds were evaluated for their antitumor activities against three cancer cell lines (H460, A549 and H226) by the MTT method and BMCL-200908069-1 as the pos. control. Most of the prepared compounds exhibited moderate cytotoxic activities and high selectivity against H460 cancer cell line and A549 compared with the pos. control compound The pharmacol. data indicated that the introduction of substituted aryl methylene group was favorable for increasing the antitumor activity. The most promising compound 6a showed a strong antitumor activity against H460, A549 and H226 cell lines with IC₅₀ values of 3.4濠电偞鎸鹃幐绱€l闁荤姾娅ｉ弸?sup>-1, 0.75濠电偞鎸鹃幐绱€l闁荤姾娅ｉ弸?sup>-1 and 0.86濠电偞鎸鹃幐绱€l闁荤姾娅ｉ弸?sup>-1, which were 2.8 to 16.8 times more active than the pos. control (9.52濠电偞鎸鹃幐绱€l闁荤姾娅ｉ弸?sup>-1, 29.24濠电偞鎸鹃幐绱€l闁荤姾娅ｉ弸?sup>-1, 36.21濠电偞鎸鹃幐绱€l闁荤姾娅ｉ弸?sup>-1), resp. Further studies are currently underway and will be reported in the future. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Related Products of 774-47-0).

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

Butcher, Ray J. et al. published their research in Acta Crystallographica, Section E: Structure Reports Online in 2007 | CAS: 210345-56-5

Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5) 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. 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.Application In Synthesis of Methyl 5-bromo-1H-indole-2-carboxylate

Methyl 5-bromo-1H-indole-2-carboxylate was written by Butcher, Ray J.;Jasinski, Jerry P.;Yathirajan, H. S.;Ashalatha, B. V.;Narayana, B.. And the article was included in Acta Crystallographica, Section E: Structure Reports Online in 2007.Application In Synthesis of Methyl 5-bromo-1H-indole-2-carboxylate This article mentions the following:

The indole ring system in Me 5-bromo-1H-indole-2-carboxylate, C₁₀H₈BrNO₂, is planar. The sum of the angles around the indole N atom (359.9闂? indicates sp²-hybridization. The carboxylate group adopts a planar arrangement with respect to the indole ring system. The crystal structure is stabilized by intermol. H-bond interactions. Crystallog. data are given. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5Application In Synthesis of Methyl 5-bromo-1H-indole-2-carboxylate).

Laufer, Stefan et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2009 | CAS: 16732-64-2

4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2) 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.Application of 16732-64-2

Investigations of SCIO-469-like compounds for the inhibition of p38 MAP kinase was written by Laufer, Stefan;Lehmann, Frank. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2009.Application of 16732-64-2 This article mentions the following:

The p38 MAP kinase is implicated in the release of the pro-inflammatory cytokines TNF婵?and IL-1b. Inhibition of cytokine release may be a useful treatment for inflammatory conditions such as rheumatoid arthritis and Crohn’s disease. A new lead structure for p38 MAP kinase inhibition was identified. Herein, we report the SAR of this new class of p38 inhibitors. In the experiment, the researchers used many compounds, for example, 4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2Application of 16732-64-2).

Ferro, Noel et al. published their research in Journal of Chemical Information and Modeling in 2006 | CAS: 1912-45-4

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. 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.Electric Literature of C10H8ClNO2

Coulomb and Overlap Self-Similarities: A Comparative Selectivity Analysis of Structure-Function Relationships for Auxin-like Molecules was written by Ferro, Noel;Gallegos, Ana;Bultinck, Patrick;Jacobsen, Hans-Joerg;Carbo-Dorca, Ramon;Reinard, Thomas. And the article was included in Journal of Chemical Information and Modeling in 2006.Electric Literature of C10H8ClNO2 This article mentions the following:

Auxins are defined mainly by a set of physiol. actions, but the structure-effect relationship still is based on chem. intuition. Currently a well-defined auxin mol. structure is not available. The existence of different auxin binding proteins and mechanisms of auxin action, the wide diversity of the auxin mols., and the pleiotropic effects of auxin imply a completely different mechanism as described for the animal hormone concept. Here, we present a computational approach dealing with semiempirical optimizations of the auxin mols. themselves, which represent a number of about 250 different chem. structures. Our approach uses mol. quantum similarity measures and addnl. quantum variables for the anal. of auxin-like mols. The finding of similarities in mols. by focusing basically on their electron structure results in new insights in the relationship of the different auxin groups. Addnl. statistical anal. allows the identification of relationships between similarity groups and their biol. activity, resp. It is postulated that the auxin-like mol. recognition depends more on specific mol. assembling states than on a specific ring system or side chain. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Electric Literature of C10H8ClNO2).

Liu, Yue et al. published their research in Advanced Synthesis & Catalysis in 2020 | CAS: 112656-95-8

7-Nitroindoline-2,3-dione (cas: 112656-95-8) 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.Reference of 112656-95-8

Palladium-Catalyzed Cascade Hydrosilylation and Amino-Methylation of Isatin Derivatives was written by Liu, Yue;Xia, Yun-Tao;Cui, Su-Hang;Ji, Yi-Gang;Wu, Lei. And the article was included in Advanced Synthesis & Catalysis in 2020.Reference of 112656-95-8 This article mentions the following:

3-Aminomethyl-3-silyloxy-2-indolones I (R₃ = Et₃, ^tBuMe₂, Bu₃; R¹ = Me, R¹₂ = CH₂CH₂OCH₂CH₂; R² = Me, MeO, halo, CO₂Me) were prepared by palladium acetate-catalyzed tandem hydrosilylative coupling of isatins with hydrosilanes HSiR₃ and formamides R¹₂NCHO. We demonstrate that using palladium acetate as a catalyst for reduction of DMF and isatin derivatives by hydrosilanes, a cascade hydrosilylation and amino-methylation reaction can be realized. With DMF as a reactant and a solvent, the in-situ generated siloxymethylamine intermediate, an adduct of DMF and hydrosilanes, smoothly participates in the successive stages, providing a serials of Si, N-functionalized indolin-2-ones in moderate to good yields. This strategy exhibits high chemoselectivity toward carbonyl moieties reduction among the substrates. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Reference of 112656-95-8).

Nguyen, Quyen et al. published their research in Journal of the American Chemical Society in 2013 | CAS: 4583-55-5

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Formula: C10H10BrN

Iron(II) bromide-catalyzed intramolecular C-H bond amination [1,2]-shift tandem reactions of aryl azides was written by Nguyen, Quyen;Nguyen, Tuyen;Driver, Tom G.. And the article was included in Journal of the American Chemical Society in 2013.Formula: C10H10BrN This article mentions the following:

Iron(II) bromide catalyzes the transformation of ortho-substituted aryl azides into 2,3-disubstituted indoles through a tandem ethereal C-H bond amination [1,2]-shift reaction. The preference for the 1,2-shift component of the tandem reaction was established to be Me < 1闂?< 2闂?< Ph. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Formula: C10H10BrN).

Nagaraja, S. N. et al. published their research in Journal of Scientific & Industrial Research in 1958 | CAS: 4583-55-5

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Reference of 4583-55-5

Synthesis of 1,3,3-trimethyl-2-methyleneindolines was written by Nagaraja, S. N.;Sunthankar, S. V.. And the article was included in Journal of Scientific & Industrial Research in 1958.Reference of 4583-55-5 This article mentions the following:

A series of 1,3,3-trimethyl-2-methyleneindolines was prepared by condensation of the substituted phenylhydrazines (I) with MeEtCO in EtOH to give the corresponding phenylhydrazones (II), cyclization of II with 2N H₂SO₄ to the corresponding 2,3-dimethylindoles (III), and methylation of III with MeI in MeOH to indoline iodides (IV). I were prepared in 40-50% yield by diazotization of the corresponding p-substituted-arylamines and reduction with acidic SnCl₂. II were prepared by addition of MeEtCO to I in EtOH, refluxing 1 hr., and distilling in vacuo; p-ClC₆H₄NHN:CMeEt b_0.6-0.7 125-30闂? yield 80%; Br derivative b_0.9 120-5闂? yield 73%. To the II, 10 parts by volume 2N H₂SO₄ was added, the mixture heated 0.5-1 hr. at 95闂? the solution cooled, and the III filtered off. The following 5-substituted III were prepared (5-substituent, % yield, and m.p. given): Cl, 80, 144-5闂? Br, 88, 142-3闂? OMe, 70, 109-10闂? OEt, 65, 114-15闂? NO₂, 60-5, 187-8闂?(prepared by nitration of III with KNO₃ and concentrated H₂SO₄ at 3闂?; NH₂, 55, 173-4闂?(prepared by reduction of the 5-NO₂ derivative of III with alkali and hydrosulfite). III 1, MeOH 10, and MeI 3 parts were heated in an autoclave 4-5 hrs. at 100-10闂? the solution cooled, the solvent evaporated, the residue extracted with boiling H₂O, the H₂O distilled in vacuo, giving 5-substituted IV. The following IV, isolated and characterized as methiodides, were prepared (5-substituent, % yield, and m.p. of methiodide given): Cl, 60, 221-2闂? OMe, 65, 221-2闂? OEt, 55, 203-4闂? NO₂, 62, 203-4闂? NH₂, 58, 190-1闂? In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Reference of 4583-55-5).

Islam, Mohammad Shahidul et al. published their research in ACS Omega in 2021 | CAS: 827-01-0

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

Construction of Spirooxindole Analogues Engrafted with Indole and Pyrazole Scaffolds as Acetylcholinesterase Inhibitors was written by Islam, Mohammad Shahidul;Al-Majid, Abdullah Mohammed;Azam, Mohammad;Verma, Ved Prakash;Barakat, Assem;Haukka, Matti;Elgazar, Abdullah A.;Mira, Amira;Badria, Farid A.. And the article was included in ACS Omega in 2021.Recommanded Product: 827-01-0 This article mentions the following:

Twenty-five new hits of spirooxindole analogs engrafted with indole and pyrazole scaffolds were designed and constructed via a [3+2]cycloaddition (32CA) reaction starting from three components: new chalcone-based indole and pyrazole scaffolds, substituted isatins, and secondary amines. The potency of the compounds were assessed in modulating cholinesterase (AChE) activity using Ellman’s method. Two compounds showed the strongest acetylcholine esterase inhibition (AChEI) with IC₅₀ values of 24.1 and 27.8濠电偞鎸鹃幏? resp. Mol. docking was used to study their interaction with the active site of hAChE. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Recommanded Product: 827-01-0).

Hegedus, Louis S. et al. published their research in Journal of Organic Chemistry in 1981 | CAS: 6639-06-1

3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Product Details of 6639-06-1

Palladium-assisted N-alkylation of indoles: attempted application to polycyclization was written by Hegedus, Louis S.;Winton, Peter M.;Varaprath, Sudarsanan. And the article was included in Journal of Organic Chemistry in 1981.Product Details of 6639-06-1 This article mentions the following:

The palladium(II) complexes of the olefins ethene, propene, and 1-hexene reacted with 1-lithioindole to produce N-alkylated indoles exclusively. Attempts to perform this N-alkylation intramol. (to form tricyclic material from 2-allylskatole) failed. Anilines with dienic side chains in the 2-position were subjected to Pd(II)-assisted cyclization conditions in attempts to induce polycyclization. However, only monocyclization was observed In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1Product Details of 6639-06-1).

Lai, Mei-Jung et al. published their research in European Journal of Medicinal Chemistry in 2019 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) 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.COA of Formula: C8H6N2O2

1-Arylsulfonyl indoline-benzamides as a new antitubulin agents, with inhibition of histone deacetylase was written by Lai, Mei-Jung;Ojha, Ritu;Lin, Mei-Hsiang;Liu, Yi-Min;Lee, Hsueh-Yun;Lin, Tony Eight;Hsu, Kai-Cheng;Chang, Chi-Yen;Chen, Mei-Chuan;Nepali, Kunal;Chang, Jang-Yang;Liou, Jing-Ping. And the article was included in European Journal of Medicinal Chemistry in 2019.COA of Formula: C8H6N2O2 This article mentions the following:

We report structure-activity relationships of 1-arylsulfonyl indoline based benzamides. The benzamide (9) exhibits striking tubulin inhibition with an IC₅₀ value of 1.1 濠电偞鎸鹃幏? better than that of combretastain A-4 (3), and substantial antiproliferative activity against a variety of cancer cells, including MDR-pos. cell lines with an IC₅₀ value of 49 nM (KB), 79 nM (A549), 63 nM (MKN45), 64 nM (KB-VIN10), 43 nM (KB-S15), and 46 nM (KB-7D). Dual inhibitory potential of compound 9 was found as it demonstrated significant inhibitory potential against HDAC1, 2 and 6 in comparison to MS-275 (6). Some key interactions of 9 with the amino acid residues of the active site of tubulin and with amino acid residues of HDAC 1 isoform have been figured out by mol. modeling. Compound 9 also demonstrated significant in vivo efficacy in the human non-small cell lung cancer A549 xenograft model as well as B-cell lymphoma BJAB xenograft tumor model. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4COA of Formula: C8H6N2O2).