Indole Building Blocks

Tian, Xing-Ling’s team published research in ACS Omega in 2020-09-01 | 950846-89-6

ACS Omega published new progress about Coating process. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Safety of 2-(2-Aminoethyl)-3′,6′-bis(diethylamino)spiro[isoindoline-1,9′-xanthen]-3-one.

Tian, Xing-Ling; Feng, Chao; Zhao, Xu-Hui published the artcile< Corrosion Monitoring Effect of Rhodamine-Ethylenediamine on Copper Relics under a Protective Coating>, Safety of 2-(2-Aminoethyl)-3′,6′-bis(diethylamino)spiro[isoindoline-1,9′-xanthen]-3-one, the main research area is rhodamine ethylenediamine copper relics protective coating corrosion.

Fluorescence spectroscopy is a common technique used to monitor early metallic corrosion. The fluorescence response characteristics of rhodamine-ethylenediamine toward Cu2+ have been studied using fluorescence and IR spectroscopy. Fluorescence microscopy and electrochem. impedance spectroscopy were used to study the monitoring effect of rhodamine-ethylenediamine on the corrosion of copper relics protected by an epoxy coating. The results showed a strong fluorescent response and selectivity toward Cu2+ that existed using rhodamine-ethylenediamine. Early metallic corrosion of copper relics can be effectively monitored upon adding 0.8 wt% rhodamine-ethylenediamine to an epoxy coating. When the soaking time was increased, the fluorescence intensity of the fluorescent area on the coating became stronger. In addition, the area of the luminous coating reached ∼0.06 mm2 and the area of corrosion under the protective coating was ∼0.008 mm2, which was about 1/10 of the fluorescence area observed on the coating.

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

Wang, Xiaodong’s team published research in Journal of Materials Chemistry B: Materials for Biology and Medicine in 2020 | 950846-89-6

Journal of Materials Chemistry B: Materials for Biology and Medicine published new progress about Autophagy. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Electric Literature of 950846-89-6.

Wang, Xiaodong; Fan, Li; Wang, Yubin; Zhang, Caihong; Liang, Wenting; Shuang, Shaomin; Dong, Chuan published the artcile< Visual monitoring of the lysosomal pH changes during autophagy with a red-emission fluorescent probe>, Electric Literature of 950846-89-6, the main research area is lysosome pH autophagy red emission fluorescent probe.

Autophagy plays crucial roles in maintaining normal intracellular homeostasis. Mol. probes capable of monitoring lysosomal pH changes during autophagy are still highly required yet challenging to develop. Here, a lysosome-targeting fluorescent pH probe, RML (I), is presented by introducing a methylcarbitol unit as the lysosome-targeting group to rhodamine B, which is highly sensitive to pH changes. RML exhibits remarkable pH-dependent behavior at 583 nm with a fluorescent enhancement of >148-fold. The pKa value is determined as 4.96, and the linear response with pH changes from 4.50-5.70, which is favorable for lysosomal pH imaging. Also RML diffuses selectively into lysosomes using confocal fluorescence microscopy. Using RML, the authors have successfully visualized autophagy by monitoring the lysosomal pH changes.

Roy, Saswati Ghosh’s team published research in New Journal of Chemistry in 2020 | 950846-89-6

New Journal of Chemistry published new progress about Colorimetric sensors. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Quality Control of 950846-89-6.

Roy, Saswati Ghosh; Mondal, Subhendu; Ghosh, Kumaresh published the artcile< Copillar[5]arene-rhodamine conjugate as a selective sensor for Hg2+ ions>, Quality Control of 950846-89-6, the main research area is copillararene rhodamine conjugate selective sensor mercury.

A new copillar[5]arene coupled rhodamine probe 1 has been designed and synthesized. The mol. probe shows selective sensing of Hg2+ ions over a series of metal ions in CH3CN by exhibiting a color change of the solution as well as ‘turn-on’ fluorescence. Compound 1 also shows interaction with Cu2+ by exhibiting a different color and spectral changes. Furthermore, Hg2+ has been differentiated from Cu2+ by using tetrabutylammonium iodide (TBAI). While in the presence of TBAI, the reddish violet color of the 1-Cu2+ complex becomes colorless with the regeneration of the original electronic spectrum of 1; under identical conditions, the pink color of the 1-Hg2+ complex is not changed in the presence of TBAI. Model compound 2 with no pillar[5]arene moiety has been synthesized to validate the role of pillararene in the selectivity of metal ion sensing. Importantly, compound 2 does not show any selectivity in sensing under identical conditions. Complexation studies are performed by using UV-vis, fluorescence, FTIR and NMR spectroscopic methods.

Duguta, Govardhan’s team published research in Chemical Data Collections in 2020-08-31 | 4771-48-6

Chemical Data Collections published new progress about Acetylation. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Electric Literature of 4771-48-6.

Duguta, Govardhan; Muddam, Bhooshan; Kamatala, Chinna Rajanna; Chityala, Yadaiah published the artcile< Symmetric trichloro triazine adducts with N, N'-dimethyl formamide and N, N'-dimethyl acetamide as green Vilsmeier -Haack reagents for effective formylation and acylation of Indoles>, Electric Literature of 4771-48-6, the main research area is trichloroisocyanuric acid dimethyl formamide indole formylation acetylation Vilsmeier Haack; indolecarbaldehyde acetylindole green chem.

Sym. trichloro triazine (trichlorotriazine (TCTA), and trichloroisocyanuric acid (TCCA)) adducts with N, N’-dimethyl formamide (DMF) N, N’-dimethyl acetamide (DMA) were explored as green Vilsmeier -Haack (VH) reagents for effective formylation and acetylation of indole. Reaction times (RT) reduced significantly in (TCTA/DMF), (TCCA/DMF), (TCTA/DMA) and (TCCA/DMA) triggered reactions followed by yield increments. Microwave assisted (MWA) protocols with these reagents reduced the reaction times from several hours to only few minutes followed by yield enhancements.

Chemical Data Collections published new progress about Acetylation. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Electric Literature of 4771-48-6.

Huang, Xu-Lun’s team published research in Organic Letters in 2020-12-18 | 399-76-8

Organic Letters published new progress about [3+2] Cycloaddition reaction (photochem., stereoselective). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Product Details of C9H6FNO2.

Huang, Xu-Lun; Cheng, Yuan-Zheng; Zhang, Xiao; You, Shu-Li published the artcile< Photoredox-Catalyzed Intermolecular Hydroalkylative Dearomatization of Electron-Deficient Indole Derivatives>, Product Details of C9H6FNO2, the main research area is indole amino acid diastereoselective hydroalkylation dearomatization photoredox; indoline stereoselective preparation lactamization; lactam fused indoline stereoselective preparation.

Dearomatization of indole derivatives offers a straightforward approach to access diverse indolines. To date, the corresponding dearomative transformations involving electron-deficient indoles are limited. Herein, we report a one-electron strategy for dearomatization of electron-deficient indoles via a photoredox-catalyzed hydroalkylation employing com. available glycine derivatives as the hydrofunctionalization reagents. Followed by DBU-mediated lactamization, structurally appealing lactam-fused indolines are obtained in good to excellent yields with exclusive selectivity.

Luo, Na’s team published research in Organic Chemistry Frontiers in 2021 | 20870-77-3

Organic Chemistry Frontiers published new progress about Cyclization. 20870-77-3 belongs to class indole-building-block, and the molecular formula is C8H6ClNO, Name: 4-Chloroindolin-2-one.

Luo, Na; Sun, Zhen-Wei; Xu, Xing-Xin; Hu, Xiao-Qiang; Jia, Feng-Cheng published the artcile< A transition-metal-free, base-promoted annulation/ring-cleavage/ring-reconstruction cascade reaction: a facile access to N-protection free indole-indenones>, Name: 4-Chloroindolin-2-one, the main research area is indole indenone preparation; arylglyoxal oxindole annulation ring cleavage construction cascade.

A one-step, transition-metal-free, base-promoted cascade reaction of 2-halogenated arylglyoxals with 2-oxindoles is reported herein, which provides a straightforward approach to structurally diverse N-protection free indole-indenones in satisfactory yields. Control experiments indicated that the geminal bisindolin-2-one intermediate played a crucial role in the downstream annulation/ring-cleavage/ring-reconstruction reaction sequence. This novel reaction not only further enriches the reactivity of indolin-2-ones as the recursive enolate anion source, but also achieves thermal-induced α-arylation of oxindoles without a transition-metal catalyst.

Organic Chemistry Frontiers published new progress about Cyclization. 20870-77-3 belongs to class indole-building-block, and the molecular formula is C8H6ClNO, Name: 4-Chloroindolin-2-one.

Kopinathan, Anitha’s team published research in Journal of Medicinal Chemistry in 2019-01-10 | 399-76-8

Journal of Medicinal Chemistry published new progress about Amidation. 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Recommanded Product: 5-Fluoroindole-2-carboxylic acid.

Kopinathan, Anitha; Draper-Joyce, Christopher; Szabo, Monika; Christopoulos, Arthur; Scammells, Peter J.; Lane, J. Robert; Capuano, Ben published the artcile< Subtle Modifications to the Indole-2-carboxamide Motif of the Negative Allosteric Modulator N-((trans)-4-(2-(7-Cyano-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)cyclohexyl)-1H-indole-2-carboxamide (SB269652) Yield Dramatic Changes in Pharmacological Activity at the Dopamine D2 Receptor>, Recommanded Product: 5-Fluoroindole-2-carboxylic acid, the main research area is SB269652 derivative preparation indolecarboxamide motif modification drug design antipsychotics.

SB269652 (I) is a neg. allosteric modulator of the dopamine D2 receptor. Herein, we present the design, synthesis, and pharmacol. evaluation of “”second generation”” analogs of I whereby subtle modifications to the indole-2-carboxamide motif confer dramatic changes in functional affinity (5000-fold increase), cooperativity (100-fold increase), and a novel action to modulate dopamine efficacy. Thus, structural changes to this region of I allows the generation of a novel set of analogs with distinct pharmacol. properties.

DeRatt, Lindsey G’s team published research in Organic Letters in 2019-12-06 | 399-76-8

Organic Letters published new progress about Heterocyclic compounds, nitrogen Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Application of C9H6FNO2.

DeRatt, Lindsey G.; Lawson, Edward C.; Wang, Chao-Yuan; Kuduk, Scott D. published the artcile< Mild Intramolecular Ring Opening of Oxetanes>, Application of C9H6FNO2, the main research area is oxetane carboxamide nucleophile intramol ring opening.

Herein, an intramol. ring opening of oxetane carboxamides with mild nucleophiles, such as nitrogen heterocycles, is presented. The reaction proceeds under metal-free basic conditions which is highly unusual in ring opening reactions of oxetanes. Amide formation and oxetane ring opening/cyclization in a one-pot approach affords high levels of mol. complexity in a single step from simple, readily available substrates.

Kufareva, Irina’s team published research in Scientific Reports in 2019-12-31 | 23077-43-2

Scientific Reports published new progress about Apoptosis. 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Reference of 23077-43-2.

Kufareva, Irina; Bestgen, Benoit; Brear, Paul; Prudent, Renaud; Laudet, Beatrice; Moucadel, Virginie; Ettaoussi, Mohamed; Sautel, Celine F.; Krimm, Isabelle; Engel, Matthias; Filhol, Odile; Borgne, Marc Le; Lomberget, Thierry; Cochet, Claude; Abagyan, Ruben published the artcile< Discovery of holoenzyme-disrupting chemicals as substrate-selective CK2 inhibitors>, Reference of 23077-43-2, the main research area is CK2 inhibitor cell growth apoptosis breast cancer.

CK2 is a constitutively active protein kinase overexpressed in numerous malignancies. Interaction between CK2a and CK2β subunits is essential for substrate selectivity. The CK2a/CK2β interface has been previously targeted by peptides to achieve functional effects; however, no small mols. modulators were identified due to pocket flexibility and open shape. Here we generated numerous plausible conformations of the interface using the fumigation modeling protocol, and virtually screened a compound library to discover compound 1 that suppressed CK2a/CK2β interaction in vitro and inhibited CK2 in a substrate-selective manner. Orthogonal SPR, crystallog., and NMR experiments demonstrated that 4 and 6, improved analogs of 1, bind to CK2a as predicted. Both inhibitors alter CK2 activity in cells through inhibition of CK2 holoenzyme formation. Treatment with 6 suppressed MDA-MB231 triple neg. breast cancer cell growth and induced apoptosis. Altogether, our findings exemplify an innovative computational-exptl. approach and identify novel non-peptidic inhibitors of CK2 subunit interface disclosing substrate-selective functional effects.

Scientific Reports published new progress about Apoptosis. 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Reference of 23077-43-2.

Lu, Wen-Jun’s team published research in Acta Crystallographica, Section E: Structure Reports Online in 2012-01-31 | 23077-43-2

Acta Crystallographica, Section E: Structure Reports Online published new progress about Crystal structure. 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Name: 5-Fluoro-1H-indole-3-carboxylic acid.

Lu, Wen-Jun; Zou, Zhi-Hong; Luo, Yang-Hui published the artcile< 5-Fluoro-1H-indole-3-carboxylic acid>, Name: 5-Fluoro-1H-indole-3-carboxylic acid, the main research area is crystal structure fluoroindolecarboxylic acid; mol structure fluoroindolecarboxylic acid; hydrogen bond fluoroindolecarboxylic acid; indolecarboxylic fluoro acid crystal mol structure.

In 5-fluoro-1H-indole-3-carboxylic acid, C9H6FNO2, the carboxyl group is twisted slightly away from the indole-ring plane [dihedral angle = 7.39(10)°]. In the crystal, carboxyl inversion dimers linked by pairs of O-H···O H bonds generate R22(8) loops and N-H···O H bonds connect the dimers into (101̅) sheets. Crystallog. data are given.