October 2022 - Page 65 of 72 - Indole Building Blocks

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, Quality Control 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>, Quality Control 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.

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

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, Formula: C30H36N4O2.

Roy, Saswati Ghosh; Mondal, Subhendu; Ghosh, Kumaresh published the artcile< Copillar[5]arene-rhodamine conjugate as a selective sensor for Hg2+ ions>, Formula: C30H36N4O2, 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.

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, Formula: C30H36N4O2.

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, Formula: C10H9NO.

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>, Formula: C10H9NO, 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, Formula: C10H9NO.

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, HPLC of Formula: 399-76-8.

Huang, Xu-Lun; Cheng, Yuan-Zheng; Zhang, Xiao; You, Shu-Li published the artcile< Photoredox-Catalyzed Intermolecular Hydroalkylative Dearomatization of Electron-Deficient Indole Derivatives>, HPLC of Formula: 399-76-8, 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, Application In Synthesis of 20870-77-3.

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>, Application In Synthesis of 20870-77-3, 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, Application In Synthesis of 20870-77-3.

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, Product Details of C9H6FNO2.

DeRatt, Lindsey G.; Lawson, Edward C.; Wang, Chao-Yuan; Kuduk, Scott D. published the artcile< Mild Intramolecular Ring Opening of Oxetanes>, Product Details 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.

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, Synthetic Route of 23077-43-2.

Lu, Wen-Jun; Zou, Zhi-Hong; Luo, Yang-Hui published the artcile< 5-Fluoro-1H-indole-3-carboxylic acid>, Synthetic Route of 23077-43-2, 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.

Zhang, Ting-Yu’s team published research in Organic Letters in 2018-01-05 | 23077-43-2

Organic Letters published new progress about Cyclization. 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Formula: C9H6FNO2.

Zhang, Ting-Yu; Liu, Chang; Chen, Chao; Liu, Jian-Xin; Xiang, Heng-Ye; Jiang, Wei; Ding, Tong-Mei; Zhang, Shu-Yu published the artcile< Copper-Mediated Cascade C-H/N-H Annulation of Indolocarboxamides with Arynes: Construction of Tetracyclic Indoloquinoline Alkaloids>, Formula: C9H6FNO2, the main research area is tetracyclic indoloquinoline alkaloid preparation cascade annulation.

An efficient and environmentally benign Cu-mediated method was developed for direct cascade C-H/N-H annulation to construct polyheterocyclic indoloquinoline scaffolds (e.g. I). This method highlights an emerging strategy for transforming inert C-H bonds into versatile functional groups in organic synthesis and provides a new versatile approach for the efficient synthesis of indolo[3,2-c] and [2,3-c]quinoline alkaloids.

Organic Letters published new progress about Cyclization. 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Formula: C9H6FNO2.

Banerjee, Sovan Lal’s team published research in Journal of Colloid and Interface Science in 2021-05-31 | 950846-89-6

Journal of Colloid and Interface Science published new progress about Antifouling agents. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Application In Synthesis of 950846-89-6.

Banerjee, Sovan Lal; Saha, Pabitra; Ganguly, Ritabrata; Bhattacharya, Koushik; Kalita, Uddhab; Pich, Andrij; Singha, Nikhil K. published the artcile< A dual thermoresponsive and antifouling zwitterionic microgel with pH triggered fluorescent ""on-off"" core>, Application In Synthesis of 950846-89-6, the main research area is thermoresponsive antifouling zwitterionic microgel fluorescence; Antifouling; Dual thermoresponsiveness; Fluorescence; LSCT; Microgel; UCST; Zwitterion.

A unique, tailor-made, zwitterionic, dual thermoresponsive and fluorescent microgel probe was synthesized via Reversible Addition Fragmentation chain-Transfer (RAFT) polymerization Microgels were prepared via oil in water (o/w) emulsion polymerization where poly(carboxybetaine) (PCB) acted as a macro-RAFT reagent as well as an emulsifier. The presence of poly(N-vinylcaprolactam) (PNVCL) in the microgel system imparts the thermoresponsiveness to the system and the presence of a rhodamine derivative as fluorophore makes it responsive to pH change of the system by showing a fluorescence emission at 580 nm (reddish orange color). The dual thermoresponsiveness [i.e. the presence of upper critical solution temperature (UCST @ 12°C) as well as lower critical solution temperature (LCST @ 33°C)] of the microgels was studied via UV-visible spectroscopy (UV-vis) and temperature responsive dynamic light scattering (DLS) analyses. Presence of the PCB in the corona-crosslinked microgel, played a vital role in the formation of self-assembled structure as well as in protein immobilization (antifouling activity). Antifouling property was studied using UV-vis spectroscopy where bovine serum albumin (BSA) was taken as a model protein. The presence of the pH-responsive fluorescence, thermoresponsiveness as well as antifouling properties makes this zwitterionic microgel system a potential a potential candidate for medical diagnostics and for drug delivery vehicles.