22/02/2023 - Page 3 of 66 - Indole Building Blocks

Nguyen, Nam Trung et al. published their research in International Immunology in 2013 | CAS: 172922-91-7

5,11-Dihydroindolo[3,2-b]carbazole-6-carbaldehyde (cas: 172922-91-7) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.HPLC of Formula: 172922-91-7

The roles of aryl hydrocarbon receptor in immune responses was written by Nguyen, Nam Trung;Hanieh, Hamza;Nakahama, Taisuke;Kishimoto, Tadamitsu. And the article was included in International Immunology in 2013.HPLC of Formula: 172922-91-7 This article mentions the following:

The wide range of effects of aryl hydrocarbon receptor on the immune system. A number of recent studies have examined the functions of aryl hydrocarbon receptor (Ahr) in the immune system. Also known as dioxin receptor, Ahr is a ligand-activated transcription factor that serves as a receptor for various environmental toxins. The functions of Ahr in T cells depend on the specific ligand bound to the receptor. For instance, binding of 2,3,7,8-tetrachlorodibenzo-p-dioxin to Ahr suppresses exptl. autoimmune encephalomyelitis (EAE) by promoting the development of Foxp3⁺ T_reg cells, whereas 6-formylindolo[3,2-b]carbazole enhances EAE by inducing the differentiation of IL-17-producing T cells. Furthermore, specifically deleting Ahr in T cells inhibits collagen-induced arthritis in mice. In macrophages and dendritic cells (DCs), Ahr is anti-inflammatory. In response to LPS, Ahr-deficient macrophages show increased production of pro-inflammatory cytokines, such as IL-6 and TNF-伪, and Ahr-deficient DCs produce less of the anti-inflammatory cytokine IL-10. In this review, we discuss the roles of Ahr in macrophages and T cells. Moreover, studies examining Ahr activation in other cell types have revealed addnl. contributions to B cell and osteoblast/osteoclast differentiation. We also briefly summarize the current understanding of regulatory mechanisms underlying Ahr activation in various cells and discuss the potential clin. implications of cell-specific targeting of Ahr in pathol. conditions of the immune system. In the experiment, the researchers used many compounds, for example, 5,11-Dihydroindolo[3,2-b]carbazole-6-carbaldehyde (cas: 172922-91-7HPLC of Formula: 172922-91-7).

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

Craig, Sandra et al. published their research in Journal of Medicinal Chemistry in 2012 | CAS: 837392-62-8

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (cas: 837392-62-8) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.COA of Formula: C15H20BNO2

Gold-Containing Indoles as Anticancer Agents That Potentiate the Cytotoxic Effects of Ionizing Radiation was written by Craig, Sandra;Gao, Lei;Lee, Irene;Gray, Thomas;Berdis, Anthony J.. And the article was included in Journal of Medicinal Chemistry in 2012.COA of Formula: C15H20BNO2 This article mentions the following:

This report describes the design and application of several distinct gold-containing indoles as anticancer agents. When used individually, all gold-bearing compounds display cytostatic effects against leukemia and adherent cancer cell lines. However, two gold-bearing indoles show unique behavior by increasing the cytotoxic effects of clin. relevant levels of ionizing radiation. Quantifying the amount of DNA damage demonstrates that each gold-indole enhances apoptosis by inhibiting DNA repair. Both Au(I)-indoles were tested for inhibitory effects against various cellular targets including thioredoxin reductase, a known target of several gold compounds, and various ATP-dependent kinases. While neither compound significantly inhibits the activity of thioreoxin reductase, both showed inhibitory effects against several kinases associated with cancer initiation and progression. The inhibition of these kinases provides a possible mechanism for the ability of these Au(I)-indoles to potentiate the cytotoxic effects of ionizing radiation. Clin. applications of combining Au(I)-indoles with ionizing radiation are discussed as a new strategy to achieve chemosensitization of cancer cells. In the experiment, the researchers used many compounds, for example, 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (cas: 837392-62-8COA of Formula: C15H20BNO2).

Zhang, Luyan et al. published their research in RSC Advances in 2015 | CAS: 5428-09-1

2-Allylisoindoline-1,3-dione (cas: 5428-09-1) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Related Products of 5428-09-1

Metal-free C-N cross-coupling of electrophilic compounds and N-haloimides was written by Zhang, Luyan;Li, Yanru;Jin, Long-Yi;Liang, Fushun. And the article was included in RSC Advances in 2015.Related Products of 5428-09-1 This article mentions the following:

The methodol. represents an elegant example of applying the halogen bond activation strategy in an organic transformation. When DBU is added, the cross-coupling reaction between alkyl halides, RX (R = Bn, Et, 2-oxocyclopentyl, etc.; X = Cl, Br, I) and N-haloimides, e.g., I occurs, resulting in the formation of aminated products e.g., II. A halogen bond activated nucleophilic substitution mechanism was proposed. In the experiment, the researchers used many compounds, for example, 2-Allylisoindoline-1,3-dione (cas: 5428-09-1Related Products of 5428-09-1).

Chen, Shuyou et al. published their research in ACS Catalysis in 2019 | CAS: 387-44-0

7-Fluoroindole (cas: 387-44-0) 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.Electric Literature of C8H6FN

C2/C4 Regioselective Heteroarylation of Indoles by Tuning C-H Metalation Modes was written by Chen, Shuyou;Zhang, Min;Su, Rongchuan;Chen, Xingyu;Feng, Boya;Yang, Yudong;You, Jingsong. And the article was included in ACS Catalysis in 2019.Electric Literature of C8H6FN This article mentions the following:

The development of a rational strategy to achieve the complete regioselectivity and the capability to switch regioselectivity is an appealing, yet challenging, puzzle in transition-metal-catalyzed oxidative Ar-H/Ar-H cross-coupling. Disclosed herein is an iridium-catalyzed C2/C4 regioselective C-H heteroarylation of indoles with the help of a pivaloyl group at the C3 position. The judicious choice of the catalytic systems allows the C2-heteroarylation of indole via a concerted metalation-deprotonation (CMD) process and the C4-heteroarylation via a trimol. electrophilic substitution (S_E3) pathway. The oxidants Cu(OAc)₂路H₂O and Ag₂O are demonstrated to play a vital role in the C2/C4 regioselectivity. In this Article, a heteroaryl-Ir(III)-heteroaryl complex prior to reductive elimination is successfully isolated and characterized, which represents the first example of capturing the bis(hetero)aryl metallic intermediate in oxidative Ar-H/Ar-H cross-coupling. The regiodivergent heteroarylation of indoles developed herein provides an opportunity to rapidly assemble diverse C4- and C2-heteroarylated indoles. In the experiment, the researchers used many compounds, for example, 7-Fluoroindole (cas: 387-44-0Electric Literature of C8H6FN).

Oh, Youri et al. published their research in International Journal of Molecular Sciences in 2021 | CAS: 271-29-4

1H-Pyrrolo[2,3-c]pyridine (cas: 271-29-4) 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. 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). SDS of cas: 271-29-4

Design and synthesis of a novel PLK1 inhibitor scaffold using a hybridized 3D-QSAR model was written by Oh, Youri;Jung, Hoyong;Kim, Hyejin;Baek, Jihyun;Jun, Joonhong;Cho, Hyunwook;Im, Daseul;Hah, Jung-Mi. And the article was included in International Journal of Molecular Sciences in 2021.SDS of cas: 271-29-4 This article mentions the following:

Polo-like kinase 1 (PLK1) plays an important role in cell cycle progression and proliferation in cancer cells. PLK1 also contributes to anticancer drug resistance and is a valuable target in anticancer therapeutics. To identify addnl. effective PLK1 inhibitors, we performed QSAR studies of two series of known PLK1 inhibitors and proposed a new structure based on a hybridized 3D-QSAR model. Given the hybridized 3D-QSAR models, we designed and synthesized 4-benzyloxy-1-(2-arylaminopyridin-4-yl)-1H-pyrazole-3-carboxamides, and we inspected its inhibitory activities to identify novel PLK1 inhibitors with decent potency and selectivity. In the experiment, the researchers used many compounds, for example, 1H-Pyrrolo[2,3-c]pyridine (cas: 271-29-4SDS of cas: 271-29-4).

Julia, Marc et al. published their research in Chimica Therapeutica in 1970 | CAS: 13754-86-4

6,7-Dihydro-1H-indol-4(5H)-one (cas: 13754-86-4) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Formula: C8H9NO

Indoles. XXII. New synthesis of the indole nucleus. Application to psilocine was written by Julia, Marc;Pascal, Yves R.. And the article was included in Chimica Therapeutica in 1970.Formula: C8H9NO This article mentions the following:

Psilocine (I, R = H, R1 = NMe2) was prepared by Vilsmeier-Haack condensation of pyrrole with H2NOC-CH2CH2CO2Me. Me 4-(2-pyrrolyl)-4-oxobutyrate was reduced (Huang-Minlon) to give 4-(2-pyrrolyl)butyric acid, whose mixed anhydride (from ClCO2Et) was cyclized with SnCl4 or ZnCl2 to 4,5,6,7-tetrahydro-4-indolone, which was aromatized with Pd-C in mesitylene. 4-Hydroxyindole was acetylated, treated with oxalyl chloride and HNMe2, and reduced with LiAlH4 to psilocine. I (R = CH2CH:CH2, iso-Pr, CH2CH2CO2H, R1 = NMe2; R = CH2CH2CONEt2, R1 = OH, Br, or NMe2) were similarly prepared In the experiment, the researchers used many compounds, for example, 6,7-Dihydro-1H-indol-4(5H)-one (cas: 13754-86-4Formula: C8H9NO).

Hearn, K. N. et al. published their research in Chemical Communications (Cambridge, United Kingdom) in 2017 | CAS: 480-91-1

Isoindolin-1-one (cas: 480-91-1) 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). SDS of cas: 480-91-1

Modular synthesis of 4-aminocarbonyl substituted 1,8-naphthalimides and application in single molecule fluorescence detection was written by Hearn, K. N.;Nalder, T. D.;Cox, R. P.;Maynard, H. D.;Bell, T. D. M.;Pfeffer, F. M.;Ashton, T. D.. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2017.SDS of cas: 480-91-1 This article mentions the following:

Robust methodol. to install amide, carbamate, urea and sulfonamide functionality to the 1,8-naphthalimide scaffold has been developed and exemplified. New benzamidonaphthalimide 6, synthesized using this approach, was found to be sensitive to base whereupon fluorescence emission strongly increases (>10-fold) and red-shifts (>4000 cm^-1). The optical properties of deprotonated 6 allow for single mol. fluorescence detection, the first example of such behavior from this class of fluorophore. In the experiment, the researchers used many compounds, for example, Isoindolin-1-one (cas: 480-91-1SDS of cas: 480-91-1).

Nakano, Shogo et al. published their research in ACS Catalysis in 2019 | CAS: 17332-70-6

2-Amino-3-(7-methyl-1H-indol-3-yl)propanoic acid (cas: 17332-70-6) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.COA of Formula: C12H14N2O2

Deracemization and Stereoinversion to Aromatic D-Amino Acid Derivatives with Ancestral L-Amino Acid Oxidase was written by Nakano, Shogo;Minamino, Yuki;Hasebe, Fumihito;Ito, Sohei. And the article was included in ACS Catalysis in 2019.COA of Formula: C12H14N2O2 This article mentions the following:

Enantiomerically pure amino acid derivatives could be foundational compounds for peptide drugs. Deracemization of racemates to L-amino acid derivatives can be achieved through the reaction of evolved D-amino acid oxidase and chem. reductants, whereas deracemization to D-amino acid derivatives has not progressed due to the difficulty associated with the heterologous expression of L-amino acid oxidase (LAAO). In this study, we succeeded in developing an ancestral LAAO (AncLAAO) bearing broad substrate selectivity (13 L-amino acids) and high productivity through an Escherichia coli expression system (鈭?0.7 mg/L). AncLAAO can be applied to perform deracemization to D-amino acids in a similar way to deracemization to L-amino acids. In fact, full conversion (>99% ee, D-form) could be achieved for 16 racemates, including nine D,L-Phe derivatives, six D,L-Trp derivatives, and a D,L-phenylglycine. Taken together, we believe that AncLAAO could be a key enzyme to obtain optically pure D-amino acid derivatives in the future. In the experiment, the researchers used many compounds, for example, 2-Amino-3-(7-methyl-1H-indol-3-yl)propanoic acid (cas: 17332-70-6COA of Formula: C12H14N2O2).

Stauffer, Frederic et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2012 | CAS: 271-29-4

1H-Pyrrolo[2,3-c]pyridine (cas: 271-29-4) 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.Formula: C7H6N2

New aromatase inhibitors from the 3-pyridyl arylether and 1-aryl pyrrolo[2,3-c]pyridine series was written by Stauffer, Frederic;Furet, Pascal;Floersheimer, Andreas;Lang, Marc. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2012.Formula: C7H6N2 This article mentions the following:

Aromatase inhibition is the new standard of care for estrogen receptor pos. breast cancer and has also potential for treatment of other diseases such as endometriosis. Simple and readily available 3-pyridyl arylethers and 1-aryl pyrrolo[2,3-c]pyridines recapitulating the key pharmacophore elements of Letrozole (1) are described and their structure-activity relationships are discussed. Potent and ligand efficient leads such as compound 23 (IC₅₀ = 59 nM on aromatase) have been identified. In the experiment, the researchers used many compounds, for example, 1H-Pyrrolo[2,3-c]pyridine (cas: 271-29-4Formula: C7H6N2).

Okamoto, Kazuhiro et al. published their research in European Journal of Organic Chemistry in 2021 | CAS: 15861-24-2

Indole-5-carbonitrile (cas: 15861-24-2) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Formula: C9H6N2

Electrochemical Synthesis of Imino-C-Nucleosides by “Reactivity Switching” Methodology for in situ Generated Glycoside Donors was written by Okamoto, Kazuhiro;Tsutsui, Mizuki;Morizumi, Haruka;Kitano, Yoshikazu;Chiba, Kazuhiro. And the article was included in European Journal of Organic Chemistry in 2021.Formula: C9H6N2 This article mentions the following:

Redox-induced regioselective C(sp³)-H C-glycosidation for unactivated prolinols was achieved by controlling the anomeric reactivity of electrochem. generated iminium cations. A mechanistic study revealed that the intermediate was pooled as covalent azaribose or iminium cation species in situ, and the electrophilicity of intermediates can be adjusted by changing coexisting acids. We found that the armed/disarmed analogy concept of traditional glycochem. can be adapted to our C-glycosidation reaction. Finally, we invented a logical synthetic methodol., named “reactivity switching” concept, and synthesized a series of imino-C-nucleosides (C-azanucleosides) based on this methodol. In the experiment, the researchers used many compounds, for example, Indole-5-carbonitrile (cas: 15861-24-2Formula: C9H6N2).