January 2023 - Page 25 of 26 - Indole Building Blocks

Wu, Jia-Hong et al. published their research in Organic Letters in 2020 | CAS: 774-47-0

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. 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). Quality Control of 5,6-Difluoroindoline-2,3-dione

Enantioselective Synthesis of Multifunctionalized 4H-Pyrans via Formal [4 + 2] Annulation Process by Bifunctional Phosphonium Salt Catalysis was written by Wu, Jia-Hong;Pan, Jianke;Du, Juan;Wang, Xiaoxia;Wang, Xuemei;Jiang, Chunhui;Wang, Tianli. And the article was included in Organic Letters in 2020.Quality Control of 5,6-Difluoroindoline-2,3-dione This article mentions the following:

A highly enantioselective formal [4 + 2] annulation involving electron-deficient allenes as C2-synthons has been developed under bifunctional phosphonium salt catalysis. With this catalytic protocol, a wide range of synthetically interesting and highly functionalized chiral 4H-pyran derivatives were readily prepared in good yields (up to 99%) with outstanding diastereo- and enantioselectivities (up to >20:1 dr, up to >99.9% ee). The utility and the practicality of this method were demonstrated by the gram-scale reaction and facile elaboration. Of note, this is the first example of an asym. annulation reaction involving allenic reactants under a phase-transfer catalysis system. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Quality Control of 5,6-Difluoroindoline-2,3-dione).

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

Wei, Zhaoxin et al. published their research in European Journal of Organic Chemistry in 2021 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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.Recommanded Product: 14204-27-4

Electrochemical Direct Thiolation of Lactams with Mercaptans: An Efficient Access to N-Acylsulfenamides was written by Wei, Zhaoxin;Wang, Renjie;Zhang, Yonghong;Wang, Bin;Xia, Yu;Abdukader, Ablimit;Xue, Fei;Jin, Weiwei;Liu, Chenjiang. And the article was included in European Journal of Organic Chemistry in 2021.Recommanded Product: 14204-27-4 This article mentions the following:

An efficient and eco-friendly electrochem. methodol. for the oxidative cross coupling hydrogen evolution (CCHE) reactions of lactams with thiols was presented. Various electron deficient N-acylsulfenamides were smoothly produced in modest to excellent yields without using any external oxidant. Elementary mechanistic insight supported a possible free radical process and hydrogen was the only side product. The approach provided a safe, convenient, and economical preparation of synthetically important N-thiophthalimides on a gram scale. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Recommanded Product: 14204-27-4).

Thatikonda, Thanusha et al. published their research in Organic Letters in 2019 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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.Category: indole-building-block

α-Angelica Lactone in a New Role: Facile Access to N-Aryl Tetrahydroisoquinolinones and Isoindolinones via Organocatalytic α-CH₂ Oxygenation was written by Thatikonda, Thanusha;Deepake, Siddharth K.;Das, Utpal. And the article was included in Organic Letters in 2019.Category: indole-building-block This article mentions the following:

A method for the direct oxidation of various N-aryl tetrahydroisoquinolines and isoindolines to the corresponding lactams using α-angelica lactone as a catalyst was developed. The utility of the method was further demonstrated by synthesis of indoprofen and indobufen. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Category: indole-building-block).

Yang, Tianbao et al. published their research in Organic Letters in 2020 | 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.Electric Literature of C8H6N2O2

CF₃SO₂Na-Mediated, UV-Light-Induced Friedel-Crafts Alkylation of Indoles with Ketones/Aldehydes and Bioactivities of Products was written by Yang, Tianbao;Lu, Huiai;Shu, Yixuan;Ou, Yifeng;Hong, Ling;Au, Chak-Tong;Qiu, Renhua. And the article was included in Organic Letters in 2020.Electric Literature of C8H6N2O2 This article mentions the following:

A concise, one-step route to produce 3,3′-diindolylmethanes (DIMs) from simple indoles and ketones or aldehydes is reported. The key step is the ready formation of indole derivatives that involves the in situ conversion of CF₃SO₂Na reagent to ·CF₃ under oxygen or air (1.0 atm) and UV irradiation It is disclosed that most of the obtained DIMs show anticancer activities in human bladder cancer cell lines EJ and T24. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Electric Literature of C8H6N2O2).

Thumser, Stefan et al. published their research in Journal of the American Chemical Society in 2021 | CAS: 774-47-0

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) 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.COA of Formula: C8H3F2NO2

All-Red-Light Photoswitching of Indirubin Controlled by Supramolecular Interactions was written by Thumser, Stefan;Koettner, Laura;Hoffmann, Nadine;Mayer, Peter;Dube, Henry. And the article was included in Journal of the American Chemical Society in 2021.COA of Formula: C8H3F2NO2 This article mentions the following:

Red-light responsiveness of photoswitches is a highly desired property for many important application areas such as biol. or material sciences. The main approach to elicit this property uses strategic substitution of long-known photoswitch motives such as azobenzenes or diarylethenes. Only very few photoswitches possess inherent red-light absorption of their core chromophore structures. Here, author present a strategy to convert the long-known purple indirubin dye into a prolific red-light-responsive photoswitch. In a supramol. approach, its photochromism can be changed from a neg. to a pos. one, while at the same time, significantly higher yields of the metastable E-isomer are obtained upon irradiation E- to Z-photoisomerization can then also be induced by red light of longer wavelengths. Indirubin therefore represents a unique example of reversible photoswitching using entirely red light for both switching directions. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0COA of Formula: C8H3F2NO2).

Sreenatha, Vasappanavara et al. published their research in Indian Journal of Chemistry 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. 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). Reference of 827-01-0

Synthesis and structural confirmation on selective N-alkylation of (Z)-5-((5-chloro-1H-indol-3-yl)methylene)thiazolidine-2,4-dione analogues with their molecular docking studies was written by Sreenatha, Vasappanavara;Prasad, Karnam Jayarampillai Rajendra. And the article was included in Indian Journal of Chemistry in 2021.Reference of 827-01-0 This article mentions the following:

In the present investigation, a series of novel (Z)-5-((5-chloro-1H-indol-3-yl)methylene)thiazolidine-2,4-dione analogs had been designed and synthesized in good yields with the objective of selective N-alkylation at thiazolidine 2,4-dione ring in competence with indole ring under basic conditions in the presence of aprotic solvent DMF. The newly synthesized compounds have been characterized by spectral data (IR, ¹H and ¹³C NMR, NOE, NOESY, ¹H-¹H-COSY and LC-MS). Further, mol. docking and ADME studies had revealed that the newly synthesized compounds have very good docking score against antidiabetic and anti-inflammation activities (PPARy and COX-2) as compared with standard rosiglitazone. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Reference of 827-01-0).

Ozdemir, Ahmet et al. published their research in European Journal of Medicinal Chemistry in 2015 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Recommanded Product: 827-01-0

Synthesis and evaluation of new indole-based chalcones as potential antiinflammatory agents was written by Ozdemir, Ahmet;Altintop, Mehlika Dilek;Turan-Zitouni, Gulhan;Ciftci, Gulsen Akalin;Ertorun, Ipek;Alatas, Ozkan;Kaplancikli, Zafer Asim. And the article was included in European Journal of Medicinal Chemistry in 2015.Recommanded Product: 827-01-0 This article mentions the following:

In the present work, new indole-based chalcone derivatives were obtained via the reaction of 5-substituted-1H-indole-3-carboxaldehydes/1-methylindole-3-carboxaldehyde with appropriate acetophenones. The synthesized compounds were studied for their in vitro COX-1 and COX-2 inhibitory activity. The most effective COX inhibitors were also evaluated for their in vivo antiinflammatory and antioxidant activities in LPS induced sepsis model. Furthermore, the CCK-8 assay was carried out to determine cytotoxic effects of all compounds against NIH/3T3 mouse embryonic fibroblast cells. 3-(5-Bromo-1H-indol-3-yl)-1-(4-cyanophenyl)prop-2-en-1-one (6) can be considered as a non-selective COX inhibitor (COX-1 IC₅₀ = 8.1 ± 0.2 μg/mL, COX-2 IC₅₀ = 9.5 ± 0.8 μg/mL), whereas 3-(5-methoxy-1H-indol-3-yl)-1-(4-(methylsulfonyl)phenyl)prop-2-en-1-one (1) inhibited only COX-1 (IC₅₀ = 8.6 ± 0.1 μg/mL). According to in vivo studies, these compounds also displayed antiinflammatory and antioxidant activities. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Recommanded Product: 827-01-0).

Miyachi, Hiroyuki et al. published their research in Chemical & Pharmaceutical Bulletin in 1996 | 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.SDS of cas: 5388-42-1

Inducer-specific regulators of tumor necrosis factor alpha production was written by Miyachi, Hiroyuki;Azuma, Akihiko;Hioki, Erika;Kobayashi, Yoshiro;Iwaski, Shiego;Hashimoto, Yuichi. And the article was included in Chemical & Pharmaceutical Bulletin in 1996.SDS of cas: 5388-42-1 This article mentions the following:

Novel potent regulators of tumor necrosis factor alpha (TNF-α) production by a human promyelocytic leukemia cell one, HL-60, were prepared All the compounds showed inducer-specific and bidirectional regulation of TNF-α production, i.e., they enhanced 12-O-tetradecanoylphorbol-13-acetate-induced TNF-α production, while they inhibited okadaic acid-induced one. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1SDS of cas: 5388-42-1).

Wang, Ning-wei et al. published their research in Huaxue Shiji in 2020 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Electric Literature of C9H6ClNO

Synthesis and antitumor activity evaluation of indole-2-carbohydrazide derivatives was written by Wang, Ning-wei;Han, Ying-long;Zhang, Guo-qiang;Huang, Xue-tao;Liu, Ming-hui;Yang, Ye-xian;Wang, Hai-jun;Bu, Ming. And the article was included in Huaxue Shiji in 2020.Electric Literature of C9H6ClNO This article mentions the following:

Using 5-chloroindole-2-carboxylic acid as starting material, seven indole-2-carbohydrazide derivatives had been synthesized, and their structures were confirmed by MS, ¹HNMR and ¹³CNMR. The antiproliferative activity of the compounds was evaluated against human colon cancer cells (HCT116), human breast cancer cells (MCF-7) and human lung cancer cells (A549) by methylthiazolyl tetrazolium (MTT) staining. The results showed that 5-chloro-N’-((5-fluoro-1H-indol-3-yl) methylene)-1H-indole-2-carbohydrazide displayed significant inhibitory activity against HCT116 cell lines with IC₅₀ value of 7.72μmol/L. Furthermore, the compound could induce HCT116 cells apoptosis in a dose-dependent manner. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Electric Literature of C9H6ClNO).

Ding, Guangni et al. published their research in Organic Letters in 2017 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Synthetic Route of C14H11NO

Reduction of Benzolactams to Isoindoles via an Alkoxide-Catalyzed Hydrosilylation was written by Ding, Guangni;Wu, Xiaoyu;Jiang, Lili;Zhang, Zhaoguo;Xie, Xiaomin. And the article was included in Organic Letters in 2017.Synthetic Route of C14H11NO This article mentions the following:

An alkoxide-catalyzed reduction of benzolactams to isoindoles with silanes was realized. With t-BuOK as the catalyst and Ph₂SiH₂ as the reductant, a series of benzolactams containing different functional groups were reduced to the corresponding isoindoles, which could be captured by N-Ph maleimide to form Diels-Alder products in moderate to good yields. Deuterium labeling studies and the hydrosilylation of benzolactam in DMF indicated that the deprotonation of benzolactams took place at C3 potion during the reduction In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Synthetic Route of C14H11NO).