22/02/2023 - Page 57 of 66 - Indole Building Blocks

Shang, Yanguo et al. published their research in Bioorganic Chemistry in 2022 | CAS: 16732-75-5

6-Chloroindole-2-carboxylic acid (cas: 16732-75-5) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Formula: C9H6ClNO2

Development of indole-2-carbonyl piperazine urea derivatives as selective FAAH inhibitors for efficient treatment of depression and pain was written by Shang, Yanguo;Wang, Minghui;Hao, Qingjing;Meng, Tao;Li, Lili;Shi, Junwei;Yang, Guoqing;Zhang, Zhilan;Yang, Kan;Wang, Jinxin. And the article was included in Bioorganic Chemistry in 2022.Formula: C9H6ClNO2 This article mentions the following:

Fatty acid amide hydrolase (FAAH), a serine hydrolase with significant role in the hydrolysis of endocannabinoids, is a promising therapeutic target for peripheral and central nervous system related disorders, including pain, neuroinflammation and depression. Employing a structure-based approach, a novel series of indole-2-carbonyl piperazine urea derivatives were designed and synthesized as FAAH inhibitors for the treatment of pain-depression comorbidity. Among them, compound 4i emerged as the most potent inhibitor (IC50 = 0.12 μM) with fine selectivity vs. CES2, ABHD6, MAGL and the cannabinoid receptor, which also displayed superior metabolic stability in human liver microsome and an adequate pharmacokinetic profile in rodents. Treatment of depressed rats with 4i demonstrated favorable antidepressant-like effects not only by increasing the level of BDNF in the hippocampus but also by restraining the apoptosis of hippocampal neurons. Also, 4i effectively suppressed the LPS-induced neuroinflammation in vitro. Moreover, 4i exhibited potent analgesic activity, which indicated its promising therapeutical application for pain and depression. These meaningful results shed light on FAAH inhibitors as promising pain-depression comorbidity therapeutics. In the experiment, the researchers used many compounds, for example, 6-Chloroindole-2-carboxylic acid (cas: 16732-75-5Formula: C9H6ClNO2).

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

Bone, Christine et al. published their research in Metabolites in 2022 | CAS: 83-34-1

3-Methyl-1H-indole (cas: 83-34-1) 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. 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). COA of Formula: C9H9N

Nuclear Receptor Pathways Mediating the Development of Boar Taint was written by Bone, Christine;Squires, E. James. And the article was included in Metabolites in 2022.COA of Formula: C9H9N This article mentions the following:

The nuclear receptors PXR, CAR, and FXR are activated by various ligands and function as transcription factors to control the expression of genes that regulate the synthesis and metabolism of androstenone and skatole. These compounds are produced in entire male pigs and accumulate in the fat to cause the development of a meat quality issue known as boar taint. The extent of this accumulation is influenced by the synthesis and hepatic clearance of androstenone and skatole. For this reason, PXR, CAR, and FXR-mediated signaling pathways have garnered interest as potential targets for specialized treatments designed to reduce the development of boar taint. Recent research has also identified several metabolites produced by gut microbes that act as ligands for these nuclear receptors (e.g., tryptophan metabolites, short-chain fatty acids, bile acids); however, the connection between the gut microbiome and boar taint development is not clear. In this review, we describe the nuclear receptor signaling pathways that regulate the synthesis and metabolism of boar taint compounds and outline the genes involved. We also discuss several microbial-derived metabolites and dietary additives that are known or suspected nuclear receptor ligands and suggest how these compounds could be used to develop novel treatments for boar taint. In the experiment, the researchers used many compounds, for example, 3-Methyl-1H-indole (cas: 83-34-1COA of Formula: C9H9N).

Tucker, Thomas J. et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2008 | CAS: 387350-92-7

5-(Methylsulfonyl)indoline (cas: 387350-92-7) 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.Computed Properties of C9H11NO2S

The design and synthesis of diaryl ether second generation HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) with enhanced potency versus key clinical mutations was written by Tucker, Thomas J.;Saggar, Sandeep;Sisko, John T.;Tynebor, Robert M.;Williams, Theresa M.;Felock, Peter J.;Flynn, Jessica A.;Lai, Ming-Tain;Liang, Yuexia;McGaughey, Georgia;Liu, Meiquing;Miller, Mike;Moyer, Gregory;Munshi, Vandna;Perlow-Poehnelt, Rebecca;Prasad, Sridhar;Sanchez, Rosa;Torrent, Maricel;Vacca, Joseph P.;Wan, Bang-Lin;Yan, Youwei. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2008.Computed Properties of C9H11NO2S This article mentions the following:

Using a combination of traditional Medicinal Chem./SAR anal., crystallog., and mol. modeling, a series of highly potent NNRTIs that possess broad antiviral activity against a number of key clin. mutations were synthesized. In the experiment, the researchers used many compounds, for example, 5-(Methylsulfonyl)indoline (cas: 387350-92-7Computed Properties of C9H11NO2S).

Poje, Goran et al. published their research in International Journal of Molecular Sciences in 2022 | CAS: 442-51-3

7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole (cas: 442-51-3) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Product Details of 442-51-3

Harmicens, Novel Harmine and Ferrocene Hybrids: Design, Synthesis and Biological Activity was written by Poje, Goran;Marinovic, Marina;Pavic, Kristina;Mioc, Marija;Kralj, Marijeta;de Carvalho, Lais Pessanha;Held, Jana;Perkovic, Ivana;Rajic, Zrinka. And the article was included in International Journal of Molecular Sciences in 2022.Product Details of 442-51-3 This article mentions the following:

Cancer and malaria are both global health threats. Due to the increase in the resistance to the known drugs, research on new active substances is a priority. Here, we present the design, synthesis, and evaluation of the biol. activity of harmicens, hybrids composed of covalently bound harmine/β-carboline and ferrocene scaffolds. Structural diversity was achieved by varying the type and length of the linker between the β-carboline ring and ferrocene, as well as its position on the β-carboline ring. Triazole-type harmicens were prepared using Cu(I)-catalyzed azide-alkyne cycloaddition, while the synthesis of amide-type harmicens was carried out by applying a standard coupling reaction. The results of in vitro biol. assays showed that the harmicens exerted moderate antiplasmodial activity against the erythrocytic stage of P. falciparum (IC50 in submicromolar and low micromolar range) and significant and selective antiproliferative activity against the MCF-7 and HCT116 cell lines (IC50 in the single-digit micromolar range, SI > 5.9). Cell localization experiments showed different localizations of nonselective harmicene 36 and HCT116-selective compound 28, which clearly entered the nucleus. A cell cycle anal. revealed that selective harmicene 28 had already induced G1 cell cycle arrest after 24 h, followed by G2/M arrest with a concomitant drastic reduction in the percentage of cells in the S phase, whereas the effect of nonselective compound 36 on the cell cycle was much less pronounced, which agreed with their different localizations within the cell. In the experiment, the researchers used many compounds, for example, 7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole (cas: 442-51-3Product Details of 442-51-3).

Boyd, Emily M. et al. published their research in Organic Letters in 2014 | CAS: 52448-17-6

(S)-2-Amino-3-(6-bromo-1H-indol-3-yl)propanoic acid (cas: 52448-17-6) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Quality Control of (S)-2-Amino-3-(6-bromo-1H-indol-3-yl)propanoic acid

Total Synthesis of (-)-Aspergilazine A was written by Boyd, Emily M.;Sperry, Jonathan. And the article was included in Organic Letters in 2014.Quality Control of (S)-2-Amino-3-(6-bromo-1H-indol-3-yl)propanoic acid This article mentions the following:

The total synthesis of (-)-aspergilazine A (I), an alkaloid possessing a rare N1′ to C6 bisindole bond, is described. A palladium-catalyzed N-arylation was used to selectively install the N1′-C6 bond in the presence of three other possible arylation sites. The ligand XPhos displayed a unique capability to efficiently carry out the N-arylation while simultaneously suppressing epimerization of the sensitive C9 stereocenters. This total synthesis has confirmed that aspergilazine A is a dimer of brevianamide F. In the experiment, the researchers used many compounds, for example, (S)-2-Amino-3-(6-bromo-1H-indol-3-yl)propanoic acid (cas: 52448-17-6Quality Control of (S)-2-Amino-3-(6-bromo-1H-indol-3-yl)propanoic acid).

Fan, Chuannan et al. published their research in Signal Transduction and Targeted Therapy in 2022 | CAS: 172922-91-7

5,11-Dihydroindolo[3,2-b]carbazole-6-carbaldehyde (cas: 172922-91-7) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles.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 C19H12N2O

OVOL1 inhibits breast cancer cell invasion by enhancing the degradation of TGF-β type I receptor was written by Fan, Chuannan;Wang, Qian;van der Zon, Gerard;Ren, Jiang;Agaser, Cedrick;Slieker, Roderick C.;Iyengar, Prasanna Vasudevan;Mei, Hailiang;ten Dijke, Peter. And the article was included in Signal Transduction and Targeted Therapy in 2022.Electric Literature of C19H12N2O This article mentions the following:

Ovo-like transcriptional repressor 1 (OVOL1) is a key mediator of epithelial lineage determination and mesenchymal-epithelial transition (MET). The cytokines transforming growth factor-B (TGF-B) and bone morphogenetic proteins (BMP) control the epithelial-mesenchymal plasticity (EMP) of cancer cells, but whether this occurs through interplay with OVOL1 is not known. Here, we show that OVOL1 is inversely correlated with the epithelial-mesenchymal transition (EMT) signature, and is an indicator of a favorable prognosis for breast cancer patients. OVOL1 suppresses EMT, migration, extravasation, and early metastatic events of breast cancer cells. Importantly, BMP strongly promotes the expression of OVOL1, which enhances BMP signaling in turn. This pos. feedback loop is established through the inhibition of TGF-B receptor signaling by OVOL1. Mechanistically, OVOL1 interacts with and prevents the ubiquitination and degradation of SMAD family member 7 (SMAD7), which is a neg. regulator of TGF-B type I receptor stability. Moreover, a small-mol. compound 6-formylindolo(3,2-b)carbazole (FICZ) was identified to activate OVOL1 expression and thereby antagonizing (at least in part) TGF-B-mediated EMT and migration in breast cancer cells. Our results uncover a novel mechanism by which OVOL1 attenuates TGF-β/SMAD signaling and maintains the epithelial identity of breast cancer cells. In the experiment, the researchers used many compounds, for example, 5,11-Dihydroindolo[3,2-b]carbazole-6-carbaldehyde (cas: 172922-91-7Electric Literature of C19H12N2O).

Zhou, Qingli et al. published their research in Organic Chemistry Frontiers in 2022 | CAS: 109524-10-9

1,3-Dioxoisoindolin-2-yl 2-phenoxyacetate (cas: 109524-10-9) 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.Recommanded Product: 1,3-Dioxoisoindolin-2-yl 2-phenoxyacetate

Electron donor-acceptor complex-catalyzed photoredox reactions mediated by DIPEA and inorganic carbonates was written by Zhou, Qingli;Sun, Chenggang Guo;Liu, Xing;Li, Xiaofan;Shao, Ziyan;Tan, Kai;Shen, Yuehai. And the article was included in Organic Chemistry Frontiers in 2022.Recommanded Product: 1,3-Dioxoisoindolin-2-yl 2-phenoxyacetate This article mentions the following:

A catalytic EDA complex, composed of DIPEA as a donor catalyst, NHPI ester as the acceptor, and inorganic carbonate as a stabilizer and electron transfer mediator, is reported. This photoactivation system is a simple, efficient and sustainable radical generation platform for developing decarboxylative reactions of NHPI esters. Alkylated coumarins, phenanthridine derivatives and tertiary oxindoles were synthesized using this approach without need of metal complex or organic dye photocatalysts. In the experiment, the researchers used many compounds, for example, 1,3-Dioxoisoindolin-2-yl 2-phenoxyacetate (cas: 109524-10-9Recommanded Product: 1,3-Dioxoisoindolin-2-yl 2-phenoxyacetate).

Ou, Wei et al. published their research in Angewandte Chemie, International Edition in 2021 | CAS: 199590-00-6

(1-Methyl-1H-indol-6-yl)methanol (cas: 199590-00-6) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.SDS of cas: 199590-00-6

Room-Temperature Palladium-Catalyzed Deuterogenolysis of Carbon Oxygen Bonds towards Deuterated Pharmaceuticals was written by Ou, Wei;Xiang, Xudong;Zou, Ru;Xu, Qing;Loh, Kian Ping;Su, Chenliang. And the article was included in Angewandte Chemie, International Edition in 2021.SDS of cas: 199590-00-6 This article mentions the following:

Site-specific incorporation of deuterium into drug mols. to study and improve their biol. properties is crucial for drug discovery and development. Herein, we describe a palladium-catalyzed room-temperature deuterogenolysis of carbon-oxygen bonds in alcs. and ketones with D₂ balloon for practical synthesis of deuterated pharmaceuticals and chems. with benzyl-site (sp³ C-H) D-incorporation. The highlights of this deoxygenative deuteration strategy are mild conditions, broad scope, practicability and high chemoselectivity. To enable the direct use of D₂O, electrocatalytic D₂O-splitting is adapted to in situ supply D₂ on demand. With this system, the precise incorporation of deuterium in the metabolic position (benzyl-site) of ibuprofen is demonstrated in a sustainable and practical way with D₂O. In the experiment, the researchers used many compounds, for example, (1-Methyl-1H-indol-6-yl)methanol (cas: 199590-00-6SDS of cas: 199590-00-6).

Zhang, Zhenzhen et al. published their research in Chinese Journal of Chemistry in 2019 | CAS: 5428-09-1

2-Allylisoindoline-1,3-dione (cas: 5428-09-1) 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. 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). Electric Literature of C11H9NO2

Copper-Catalyzed Carbotrifluoromethylation of Unactivated Alkenes Driven by Trifluoromethylation of Alkyl Radicals was written by Zhang, Zhenzhen;Zhu, Lin;Li, Chaozhong. And the article was included in Chinese Journal of Chemistry in 2019.Electric Literature of C11H9NO2 This article mentions the following:

Herein an unprecedented protocol for radical carbotrifluoromethylation of unactivated alkenes is reported. With Cu(OTf)₂ as the catalyst, the reaction of unactivated alkenes, TMSCF₃ and activated alkyl chlorides at room temperature provides the corresponding carbotrifluoromethylation products in satisfactory yields. Directed by trifluoromethylation of alkyl radicals, the method exhibits an excellent regioselectivity that is opposite to those driven by CF₃ radical addition In the experiment, the researchers used many compounds, for example, 2-Allylisoindoline-1,3-dione (cas: 5428-09-1Electric Literature of C11H9NO2).

Azizi, Najmodin et al. published their research in Journal of Molecular Catalysis A: Chemical in 2007 | CAS: 151358-48-4

DIM-C-pPhCO2Me (cas: 151358-48-4) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. 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: 151358-48-4

Highly efficient synthesis of bis(indolyl)methanes in water was written by Azizi, Najmodin;Torkian, Lalleh;Saidi, Mohammad R.. And the article was included in Journal of Molecular Catalysis A: Chemical in 2007.SDS of cas: 151358-48-4 This article mentions the following:

A simple, atom economy and highly efficient green protocol have been developed for synthesis of bis(indolyl)alkanes, e.g., I, by the reaction of indole derivatives with aldehydes and ketones in the presence of small amount of the heteropoly acids in water. In the experiment, the researchers used many compounds, for example, DIM-C-pPhCO2Me (cas: 151358-48-4SDS of cas: 151358-48-4).