February 2023 - Page 99 of 117 - Indole Building Blocks

Shirakawa, Seiji et al. published their research in Organic Letters in 2013 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.HPLC of Formula: 14204-27-4

Design of Chiral Bifunctional Quaternary Phosphonium Bromide Catalysts Possessing an Amide Moiety was written by Shirakawa, Seiji;Tokuda, Takashi;Kasai, Atsuyuki;Maruoka, Keiji. And the article was included in Organic Letters in 2013.HPLC of Formula: 14204-27-4 This article mentions the following:

Novel bifunctional quaternary phosphonium bromides possessing an amide moiety were designed for the highly enantioselective sulfenylation and chlorination of 尾-ketoesters under base-free phase-transfer conditions [e.g., sulfenylation of tert-Bu 1-oxo-2-indancarboxylate with N-(phenylthio)phthalimide in water/toluene in presence of sulfonium catalyst I.Br^– afforded II (98% yield, 94% ee)]. The tuning of an amide moiety of the catalyst was crucial to achieve high reactivity and enantioselectivity. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4HPLC of Formula: 14204-27-4).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Fang, Zhang et al. published their research in European Journal of Organic Chemistry in 2022 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. 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.Safety of 2-Phenylisoindolin-1-one

A New Approach to Isoindolinones: Rhodium(III)-Catalyzed [3+2] Annulation Reactions of N-Methoxybenzamides with Bis(tosylamido)methane was written by Fang, Zhang;Shu, Sai;Zhou, Guanyu;Deng, Zefeng;Huang, Pengcheng;Li, Bao;Zhao, Yingsheng. And the article was included in European Journal of Organic Chemistry in 2022.Safety of 2-Phenylisoindolin-1-one This article mentions the following:

A new approach to the synthesis of isoindolinones I (R = H, Me, OMe, etc.; R¹ = Me, OPh, Cl, etc.; R² = Cl, Me, (cyclopropylmethyl)oxidanyl, etc.; R³ = H, Cl; R⁴ = H, 2-Me, 4-Br, etc.) via direct coupling of N-methoxybenzamides 2R-3R¹-4R²-5R³C₆HC(O)NHOMe and bis(tosylamido)methane (R⁴NH)₂CH₂ with rhodium(III) as catalyst has been developed. The reaction is performed under mild conditions without oxidant, and is compatible with various functional groups. Compared with the previously reported methods for constructing isoindolinone skeletons, this method involves a novel [3+2] cyclization, and affords a wide variety of isoindolinones I in moderate to excellent yields. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Safety of 2-Phenylisoindolin-1-one).

Krishna Rao, N. et al. published their research in Pharma Chemica in 2017 | 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Related Products of 827-01-0

An improved synthesis, characterization and bioevalution of Schiff base containing benzimidazole moiety catalyzed by methane sulfonic acid was written by Krishna Rao, N.;Surendra, Babu M. S.;Ramana, N.;Tentu, Nageswara Rao;Basaveswara Rao, M. V.;Karri, Apparao. And the article was included in Pharma Chemica in 2017.Related Products of 827-01-0 This article mentions the following:

An improved process for the synthesis for some novel Schiff bases I [R = H, Me, Cl, etc.] by the reaction of 2-amino benzimidazole with 5-substituted indole-3-carbaldehyde using methane sulfonic acid as catalyst under solvent free conditions at room temp was reported. The intermediate moiety 2-aminobenzimidazole could be synthesized by reacting o-phenylene diamine with cyanobromide in the presence of acid medium. All compounds were screened for their antibacterial activities and compounds I [R = Br, Cl] exhibited high antibacterial activity potential. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Related Products of 827-01-0).

Khaledi, Hamid et al. published their research in Archiv der Pharmazie (Weinheim, Germany) in 2011 | 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Application of 827-01-0

Antioxidant, Cytotoxic Activities, and Structure-Activity Relationship of Gallic Acid-based Indole Derivatives was written by Khaledi, Hamid;Alhadi, Abeer A.;Yehye, Wagee A.;Ali, Hapipah Mohd.;Abdulla, Mahmood A.;Hassandarvish, Pouya. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2011.Application of 827-01-0 This article mentions the following:

A new series of gallic hydrazones containing an indole moiety was synthesized through the reaction of gallic hydrazide and different indole carboxaldehydes. Their antioxidant activities were determined on DPPH radical scavenging and inhibition of lipid peroxidation The in-vitro cytotoxic activities of the compounds were evaluated against HCT-116 (human colon cancer cell line) and MCF-7 (estrogen-dependent human breast cancer cell line) by the MTT method. An attempt to correlate the biol. results with their structural characteristics has been done. A limited pos. structure activity relationship was found between cytotoxic and antioxidant activities. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Application of 827-01-0).

Jung, So Hyun et al. published their research in Asian Journal of Organic Chemistry in 2019 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.SDS of cas: 14204-27-4

Enantioselective Synthesis of Chiral 伪-Alkylthiomalonates via a Phase-Transfer-Catalyzed 伪-Sulfenylation of 伪-Alkylmalonates was written by Jung, So Hyun;Kim, Byungsoo;Park, Cheonhyoung;Kim, Jeongseok;Ha, Min Woo;Hong, Suckchang;Park, Hyeung-geun. And the article was included in Asian Journal of Organic Chemistry in 2019.SDS of cas: 14204-27-4 This article mentions the following:

A synthetic method for accessing chiral 伪-alkylthio-伪-alkylmalonates I (R = allyl, i-Pr, C₆H₅, etc.) was successfully established. The enantioselective 伪-sulfenylation of 伪-alkylmalonates via phase-transfer catalysis [N-alkylthiophthalimide, 50% aqueous KOH, toluene, -40掳 and N-2′,3′,4′-trifluorophenyl-dihydroquinidium bromide] provided the corresponding 伪-alkylthio-伪-alkylmalonates in high chem. yields (up to 97%) and optical purities (up to 90% ee). In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4SDS of cas: 14204-27-4).

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.SDS of cas: 14204-27-4

Bujok, Robert et al. published their research in Synlett in 2012 | CAS: 3484-23-9

2-Methyl-6-nitro-1H-indole (cas: 3484-23-9) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.HPLC of Formula: 3484-23-9

Expedient synthesis of 1-hydroxy-4- and 1-hydroxy-6-nitroindoles was written by Bujok, Robert;Wrobel, Zbigniew;Wojciechowski, Krzysztof. And the article was included in Synlett in 2012.HPLC of Formula: 3484-23-9 This article mentions the following:

Reaction of 伪-chloroalkyl ketones with 1,3-dinitrobenzenes provided 2,4-dinitrobenzyl ketones, which on reduction with SnCl₂ gave 6-nitro derivatives of 1-hydroxyindoles. An alternative approach is the condensation of 2,4- and 2,6-dinitrotoluenes with (CO₂Et)₂ or F₃CCO₂Et to yield dinitrobenzyl ketones, which on reduction with SnCl₂ afforded nitro derivatives of 1-hydroxyindol-2-carboxylates or 1-hydroxy-2-(trifluoromethyl)indoles, resp. In the experiment, the researchers used many compounds, for example, 2-Methyl-6-nitro-1H-indole (cas: 3484-23-9HPLC of Formula: 3484-23-9).

Jiang, Huanfeng et al. published their research in Journal of Organic Chemistry in 2017 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Computed Properties of C8H6N2O2

Copper-Catalyzed Aerobic Oxidative Regioselective Thiocyanation of Aromatics and Heteroaromatics was written by Jiang, Huanfeng;Yu, Wentao;Tang, Xiaodong;Li, Jianxiao;Wu, Wanqing. And the article was included in Journal of Organic Chemistry in 2017.Computed Properties of C8H6N2O2 This article mentions the following:

A copper-catalyzed aerobic oxidative reaction between aromatics or heteroaromatics with KSCN is developed by using O₂ as the oxidant. The combination of Cu(OTf)₂, N,N,N’,N’-tetramethylethylenediamine (TMEDA) and BF₃路Et₂O provides an efficient catalytic system, affording substituted thiocyanation products and 2-aminobenzothiazoles in excellent yields. The reaction also possesses a good functional group tolerance for both strong electron-withdrawing and electron-donating groups. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Computed Properties of C8H6N2O2).

Clavadetscher, Jessica et al. published their research in Angewandte Chemie, International Edition in 2017 | CAS: 754214-56-7

7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7) 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.SDS of cas: 754214-56-7

In-cell dual drug synthesis by cancer-targeting palladium catalysts was written by Clavadetscher, Jessica;Indrigo, Eugenio;Chankeshwara, Sunay V.;Lilienkampf, Annamaria;Bradley, Mark. And the article was included in Angewandte Chemie, International Edition in 2017.SDS of cas: 754214-56-7 This article mentions the following:

Transition metals have been successfully applied to catalyze non-natural chem. transformations within living cells, with the highly efficient labeling of subcellular components and the activation of prodrugs. In vivo applications, however, have been scarce, with a need for the specific cellular targeting of the active transition metals. Here, we show the design and application of cancer-targeting palladium catalysts, with their specific uptake in brain cancer (glioblastoma) cells, while maintaining their catalytic activity. In these cells, for the first time, two different anticancer agents were synthesized simultaneously intracellularly, by two totally different mechanisms (in situ synthesis and decaging), enhancing the therapeutic effect of the drugs. Tumor specificity of the catalysts together with their ability to perform simultaneous multiple bioorthogonal transformations will empower the application of in vivo transition metals for drug activation strategies. In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7SDS of cas: 754214-56-7).

Cheng, Cheng et al. published their research in Tetrahedron in 2015 | 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. 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.HPLC of Formula: 3484-23-9

One-pot three-component reactions of methyl ketones, phenols and a nucleophile: an expedient way to synthesize densely substituted benzofurans was written by Cheng, Cheng;Liu, Changhui;Gu, Yanlong. And the article was included in Tetrahedron in 2015.HPLC of Formula: 3484-23-9 This article mentions the following:

Three-component reactions of glyoxals R¹C(O)CHO (R¹ = C₆H₅, 1-benzofuran-2-yl, cyclopropyl, etc.), sesamol/1,4-benzenediol/1,2,4-benzenetriol/phenol and indoles I (R² = H, CH₃, C₆H₅, CO₂CH₂CH₃; R³ = H, Et; R⁴ = H, 6-NO₂, 5-CH₃) were developed with the aid of acid-catalyst, which produced various densely substituted benzofurans e.g., II with good to excellent yields. On the basis of this observation, a one-pot, step-wise reaction was developed by using Me ketones R⁵C(O)CH₃ (R⁵ = t-Bu, Ph, fluoren-2-yl, thiophen-2-yl, etc.) instead of using glyoxal component in I₂/DMSO system. The indole component can be replaced by some other nucleophiles, such as 1,2,4-trimethoxybenzene and thiophenol. In the experiment, the researchers used many compounds, for example, 2-Methyl-6-nitro-1H-indole (cas: 3484-23-9HPLC of Formula: 3484-23-9).

Yuan, Yu-Chao et al. published their research in Catalysis Science & Technology in 2019 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Recommanded Product: 5388-42-1

Site-selective Ru-catalyzed C-H bond alkenylation with biologically relevant isoindolinones: a case of catalyst performance controlled by subtle stereo-electronic effects of the weak directing group was written by Yuan, Yu-Chao;Bruneau, Christian;Roisnel, Thierry;Gramage-Doria, Rafael. And the article was included in Catalysis Science & Technology in 2019.Recommanded Product: 5388-42-1 This article mentions the following:

Alkenylated isoindolinones I [R = CO₂Me, Ph, 4-FC₆H₄, etc.; R¹ = H; R² = H, Me, Cl, MeO, CN, CO₂Et; R³ = R⁴ = H, Me, MeO; R¹R² = OCH₂O] were prepared via site-selective Ru-catalyzed C-H bond alkenylation of isoindolinones with alkenes. Notably, besides the presence of two aromatic C-H sites available for functionalization, selective mono-alkenylation in the ortho-position with respect to the nitrogen atom were achieved with a readily available ruthenium catalyst. The scalability, versatility and high functional group tolerance of the catalysis enabled the late-stage functionalization of biol. relevant indoprofen and further derivatizations. Preliminary mechanistic studies indicated, the ease of the C-H bond activation step, the key role of the carbonyl group as a weak directing group throughout the catalytic cycle and the unexpected subtle differences associated between cyclic amides and imides as weak directing groups in ruthenium-catalyzed C-H bond alkenylation reactions. The isolation and role of an unprecedented off-cycle ruthenium complex was discussed as well. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Recommanded Product: 5388-42-1).