20/10/2022 - Page 6 of 8 - Indole Building Blocks

Kleinmans, Roman’s team published research in Nature (London, United Kingdom) in 2022-05-19 | 399-76-8

Nature (London, United Kingdom) published new progress about [2+2] Cycloaddition reaction, stereoselective (regioselective, photochem.). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, COA of Formula: C9H6FNO2.

Kleinmans, Roman; Pinkert, Tobias; Dutta, Subhabrata; Paulisch, Tiffany O.; Keum, Hyeyun; Daniliuc, Constantin G.; Glorius, Frank published the artcile< Intermolecular [2π+2σ]-photocycloaddition enabled by triplet energy transfer>, COA of Formula: C9H6FNO2, the main research area is bicyclohexane preparation thioxanthone catalyst diastereoselective regioselective; coumarin flavone indole bicyclobutane intermol photocycloaddition.

For more than one century, photochem. [2+2]-cycloadditions have been used by synthetic chemists to make cyclobutanes, four-membered carbon-based rings. In this reaction, typically two olefin subunits (two π-electrons per olefin) cyclize to form two new C-C σ-bonds. Although the development of photochem. [2+2]-cycloadditions has made enormous progress within the last century, research has been focused on such [2π+2π]-systems, in which two π-bonds are converted into two new σ-bonds. Here an intermol. [2+2]-photocycloaddition that uses bicyclo[1.1.0]butanes as 2σ-electron reactants was reported. This strain-release-driven [2π+2σ]-photocycloaddition reaction was realized by visible-light-mediated triplet energy transfer catalysis. A simple, modular and diastereoselective synthesis of bicyclo[2.1.1]hexanes from heterocyclic olefin coupling partners, namely coumarins, flavones and indoles, is disclosed. Given the increasing importance of bicyclo[2.1.1]hexanes as bioisosteres-groups that convey similar biol. properties to those they replace-in pharmaceutical research and considering their limited access, there remains a need for new synthetic methodologies. Applying this strategy enabled to extend the intermol. [2+2]-photocycloadditions to σ-bonds and provides previously inaccessible structural motifs.

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

Erdemir, Serkan’s team published research in Sensors and Actuators, B: Chemical in 2019-07-01 | 950846-89-6

Sensors and Actuators, B: Chemical published new progress about Density functional theory. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Application of C30H36N4O2.

Erdemir, Serkan published the artcile< Fluorometric dual sensing of Hg2+ and Al3+ by novel triphenylamine appended rhodamine derivative in aqueous media>, Application of C30H36N4O2, the main research area is triphenylamine appended rhodamine derivative mercury detection density functional theory.

Triphenylamine appended rhodamine (named probe TR) was built as a selective fluorescent probe for Al3+ and Hg2+ ions through different sensing mechanisms. TR demonstrated a distinct fluorescence enhancing at 501 and 580 nm towards Al3+ and Hg2+ ions due to the “”PET-off”” (Photoinduced electron transfer-off) and “”FRET-on”” (Fluorescence resonance energy transfer-on) processes, resp. The binding modes between TR with Al3+ and Hg2+ were found to be 1:1 by job plot anal. The limits of detection of TR for sensing Al3+ and Hg2+ are down to 71.8 nM and 0.48 μM, resp. At the same time, the complexation details between the probe TR with Al3+ and Hg2+ ions were investigated by FTIR, 1HNMR experiments and DFT calculations Moreover, simple test papers coated probe TR were successively developed for the rapid monitoring of Al3+ and Hg2+ ions.

Huang, Yong’s team published research in Chemistry – An Asian Journal in 2015 | 4771-48-6

Chemistry – An Asian Journal published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Application In Synthesis of 4771-48-6.

Huang, Yong; Song, Liangliang; Gong, Lei; Meggers, Eric published the artcile< Asymmetric Synthesis of Hydrocarbazoles Catalyzed by an Octahedral Chiral-at-Rhodium Lewis Acid>, Application In Synthesis of 4771-48-6, the main research area is hydrocarbazole enantioselective synthesis regioselective synthesis; vinylindole carboxylic ester substituted unsaturated acyl imidazole; Diels Alder reaction chiral Rh complex catalyst; Diels-Alder; asymmetric catalysis; chiral-at-metal; hydrocarbazoles; rhodium.

A bis-cyclometalated chiral-at-metal rhodium complex catalyzes the Diels-Alder reaction between N-Boc-protected 3-vinylindoles (Boc=tert-butyloxycarbonyl) and β-carboxylic ester-substituted α,β-unsaturated 2-acyl imidazoles with good-to-excellent regioselectivity (up to 99:1) and excellent diastereoselectivity (>50:1 d.r.) as well as enantioselectivity (92-99 % ee), e. g., I, under optimized conditions. The rhodium catalyst serves as a chiral Lewis acid to activate the 2-acyl imidazole dienophile by two-point binding and overrules the preferred regioselectivity of the uncatalyzed reaction.

Zhou, Zijun’s team published research in Organic Letters in 2017-01-06 | 4771-48-6

Organic Letters published new progress about Alkylation catalysts, stereoselective. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Application In Synthesis of 4771-48-6.

Zhou, Zijun; Li, Yanjun; Gong, Lei; Meggers, Eric published the artcile< Enantioselective 2-Alkylation of 3-Substituted Indoles with Dual Chiral Lewis Acid/Hydrogen-Bond-Mediated Catalyst>, Application In Synthesis of 4771-48-6, the main research area is enantioselective alkylation indole unsaturated acylimidazole chiral cyclometalated iridium complex; bifunctional chiral Lewis acid hydrogen bond mediated alkylation catalyst; pyrroloindole preparation.

A chiral-at-metal bis-cyclometalated iridium complex combines electrophile activation via metal coordination with nucleophile activation through hydrogen bond formation [e.g., indole I + acylimidazole II → III (89% conversion, 98% ee (S)) in presence of Δ-Ir complex IV.BARF]. This new bifunctional chiral Lewis acid/hydrogen-bond-mediated catalyst permits the challenging enantioselective 2-alkylation of 3-substituted indoles with α,β-unsaturated 2-acylimidazoles in up to 99% yield and with up to 98% enantiomeric excess at a catalyst loading of 2 mol %. As an application, the straightforward synthesis of a chiral pyrrolo[1,2-a]indole is demonstrated.

Wu, Zi-ying’s team published research in New Journal of Chemistry in 2019 | 950846-89-6

New Journal of Chemistry published new progress about Fluorescence spectroscopy. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Category: indole-building-block.

Wu, Zi-ying; Xu, Zhong-yong; Yan, Jin-wu; Li, Yafang; Kou, Qiuye; Zhang, Lei published the artcile< Development of rhodamine-based fluorescent probes for sensitive detection of Fe3+ in water: spectroscopic and computational investigations>, Category: indole-building-block, the main research area is rhodamine iron water fluorescent probe.

Four novel rhodamine-based fluorescent probes (RE1-RE4) were designed and synthesized for sensitive detection of Fe3+ in H2O. RE1-RE4 exhibited low detection limits in the range of 18.6 nM to 29.4 nM. The binding modes of the probes (RE1-RE4) with Fe3+ are 1:1 stoichiometry of the complexes by Job’s plot and also their complexing ability was determined using the binding constants (RE2 > RE4 > RE3 > RE1). RE2 was selected to study the proposed binding mechanism with Fe3+ by ESI-MS, 1H NMR and DFT calculations Also, RE2 was further used to detect Fe3+ in living cells and real H2O samples, indicating its promising prospect in biol. and environmental fields.

Song, Fan’s team published research in Analyst (Cambridge, United Kingdom) in 2019 | 950846-89-6

Analyst (Cambridge, United Kingdom) published new progress about Colorimetric sensors. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Formula: C30H36N4O2.

Song, Fan; Yang, Chao; Liu, Haibo; Gao, Zhigang; Zhu, Jing; Bao, Xiaofeng; Kan, Chun published the artcile< Dual-binding pyridine and rhodamine B conjugate derivatives as fluorescent chemosensors for ferric ions in aqueous media and living cells>, Formula: C30H36N4O2, the main research area is pyridine rhodamine conjugate derivative fluorescence chemosensor ferric ion.

Two new pyridine-type rhodamine B chemosensors (RBPO and RBPF) used to detect Fe3+ have been designed and synthesized, and the sensing behavior towards various metal ions was evaluated via UV-vis and fluorescence spectroscopic techniques. Both RBPO and RBPF not only have good spectral responses to Fe3+ in an EtOH/H2O solution (3 : 1, volume/volume, HEPES, 0.5 mM, pH = 7.33) with low detection limits and high binding constants, but also suffer from less interference from common metal cations. The two chemosensors are further proven to be practical in sensitively monitoring trace Fe3+ in real water specimens. Intracellular imaging applications demonstrated that RBPO and RBPF can be used as two fluorescent chemosensors for the detection of Fe3+ in living human breast adenocarcinoma (MCF-7) cells.

Seal, Jonathan T’s team published research in Journal of Medicinal Chemistry in 2020-09-10 | 93247-78-0

Journal of Medicinal Chemistry published new progress about Anti-inflammatory agents. 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Reference of 93247-78-0.

Seal, Jonathan T.; Atkinson, Stephen J.; Aylott, Helen; Bamborough, Paul; Chung, Chun-wa; Copley, Royston C. B.; Gordon, Laurie; Grandi, Paola; Gray, James R. J.; Harrison, Lee A.; Hayhow, Thomas G.; Lindon, Matthew; Messenger, Cassie; Michon, Anne-Marie; Mitchell, Darren; Preston, Alex; Prinjha, Rab K.; Rioja, Inmaculada; Taylor, Simon; Wall, Ian D.; Watson, Robert J.; Woolven, James M.; Demont, Emmanuel H. published the artcile< The Optimization of a Novel, Weak Bromo and Extra Terminal Domain (BET) Bromodomain Fragment Ligand to a Potent and Selective Second Bromodomain (BD2) Inhibitor>, Reference of 93247-78-0, the main research area is second bromodomain inhibitor.

The profound efficacy, yet associated toxicity of pan-BET inhibitors is well documented. The possibility of an ameliorated safety profile driven by significantly selective (>100-fold) inhibition of a subset of the eight bromodomains is enticing, but challenging given the close homol. Herein, we describe the X-ray crystal structure-directed optimization of a novel weak fragment ligand with a pan-second bromodomain (BD2) bias, to potent and highly BD2 selective inhibitors. A template hopping approach, enabled by our parallel research into an orthogonal template (15, GSK046, I), was the basis for the high selectivity observed This culminated in two tool mols., 20 (GSK620) and 56 (GSK549), which showed an anti-inflammatory phenotype in human whole blood, confirming their cellular target engagement. Excellent broad selectivity, developability, and in vivo oral pharmacokinetics characterize these tools, which we hope will be of broad utility to the field of epigenetics research.

Gao, Zhigang’s team published research in Tetrahedron in 2019-03-01 | 950846-89-6

Tetrahedron published new progress about Biocompatibility. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Recommanded Product: 2-(2-Aminoethyl)-3′,6′-bis(diethylamino)spiro[isoindoline-1,9′-xanthen]-3-one.

Gao, Zhigang; Kan, Chun; Liu, Haibo; Zhu, Jing; Bao, Xiaofeng published the artcile< A highly sensitive and selective fluorescent probe for Fe3+ containing two rhodamine B and thiocarbonyl moieties and its application to live cell imaging>, Recommanded Product: 2-(2-Aminoethyl)-3′,6′-bis(diethylamino)spiro[isoindoline-1,9′-xanthen]-3-one, the main research area is iron ion fluorescent probe rhodamine B thiocarbonyl moiety bioimaging.

A novel turn-on rhodamine B-based fluorescent chemosensor (RBCS) was designed and synthesized by reacting N-(rhodamine B)lactam-1,2-ethylenediamine and carbon disulfide. Upon addition of Fe3+ in EtOH/H2O solution (2:1, volume/volume, HEPES buffer, 0.6 mM, pH 7.20), the RBCS displayed a significant fluorescence enhancement at 582 nm and a dramatic color change from colorless to pink, which can be detected by the naked eye. Significantly, the RBCS exhibited a highly selective and sensitive ability toward Fe3+. The detection limit of the probe was 2.05 × 10-7 M. Job’s plot indicated the formation of 1:1 complex between the RBCS and Fe3+. Moreover, the practical use of the RBCS is demonstrated by its application in the detection of Fe3+ in HeLa cells.

Xu, Hai-Feng’s team published research in Journal of Organic Chemistry in 2021-01-15 | 399-76-8

Journal of Organic Chemistry published new progress about Amides, secondary 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, Recommanded Product: 5-Fluoroindole-2-carboxylic acid.

Xu, Hai-Feng; Pan, You-Lu; Li, Gang-Jian; Hu, Xu-Yang; Chen, Jian-Zhong published the artcile< Copper(II)-Catalyzed Direct C-H (Hetero)arylation at the C3 Position of Indoles Assisted by a Removable N,N-Bidentate Auxiliary Moiety>, Recommanded Product: 5-Fluoroindole-2-carboxylic acid, the main research area is arylated indole regioselective preparation; indole arylboronic ester arylation copper catalyst.

The regioselective arylation of inert C3-H bonds in indoles reacting with arylboronates via effective copper-mediated catalysis with the aid of a facile and removable 2-pyridinylisopropyl (PIP) group without ligand participation was reported. This newly established method features high compatibility with diverse functional groups between coupling partners, including both indole substrates and arylboron reagents, consequentially leading to operational simplicity and providing access to generate the desired arylated products I [R = H, 4-Me, 5-MeO, 6-Br, etc.; R1 = Me, Bn; Ar = Ph, 2-thienyl, 3-pyridyl, etc.] in good to excellent yields of up to 97%. Synthetically, the PIP-derived amide moiety could subsequently be readily removed under mild reaction conditions to produce useful indolecarboxylic acids for further transformation.

Das, Sujoy’s team published research in ACS Omega in 2019-03-31 | 950846-89-6

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

Das, Sujoy; Rissanen, Kari; Sahoo, Prithidipa published the artcile< Rare Crystal Structure of Open Spirolactam Ring along with the Closed-Ring Form of a Rhodamine Derivative: Sensing of Cu2+ Ions from Spinach>, Name: 2-(2-Aminoethyl)-3′,6′-bis(diethylamino)spiro[isoindoline-1,9′-xanthen]-3-one, the main research area is crystal structure spirolactam ring copper ion spinach.

Crystal structures of a rhodamine derivative in its closed and open spirolactam ring form combined with a selective and sensitive detection of Cu2+ ion at micromolar range in neutral medium. The chemosensing properties of the probe through a pentacoordinate Cu2+ ion were proven by spectroscopic and theor. anal. The spirolactam ring opening as the Cu2+ selective sensor was applied to spinach (Spinacia oleracea) to estimate the accumulation of copper as copper(II) into the plant.