Indole Building Blocks

Qin, Jing-Hao’s team published research in Angewandte Chemie, International Edition in 2021-01-25 | 93247-78-0

Angewandte Chemie, International Edition published new progress about [2+2+2] Cycloaddition reaction. 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Reference of 93247-78-0.

Qin, Jing-Hao; Luo, Mu-Jia; An, De-Lie; Li, Jin-Heng published the artcile< Electrochemical 1,2-Diarylation of Alkenes Enabled by Direct Dual C-H Functionalizations of Electron-Rich Aromatic Hydrocarbons>, Reference of 93247-78-0, the main research area is alkene arene cobalt electrochem diarylation dehydrogenative cycloaddition annulation cascade; aryl alkene preparation; dihydroindolo carbazole preparation; alkenes; dehydrogenative [2+2+2] cycloaddition; diarylation; electrochemistry; polyarenes.

A cobalt-promoted electrochem. 1,2-diarylation of alkenes with electron-rich aromatic hydrocarbons via direct dual C-H functionalizations is described, which employs a radical relay strategy to produce polyaryl-functionalized alkanes. Simply by using graphite rod cathode instead of platinum plate cathode, chemoselectivity of this radical relay strategy is shifted to the dehydrogenative [2+2+2] cycloaddition via 1,2-diarylation, annulation, and dehydrogenation cascades leading to complex 11,12-dihydroindolo[2,3-a]carbazoles. Mechanistical studies indicate that a key step for the radical relay processes is transformations of the aromatic hydrocarbons to the aryl sp2-hybridized carbon-centered radicals via deprotonation of the corresponding aryl radical cation intermediates with bases.

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

Boyd, Olivia’s team published research in Angewandte Chemie, International Edition in 2019 | 399-76-8

Angewandte Chemie, International Edition published new progress about C-C bond activation. 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Recommanded Product: 5-Fluoroindole-2-carboxylic acid.

Boyd, Olivia; Wang, Gang-Wei; Sokolova, Olga O.; Calow, Adam D. J.; Bertrand, Sophie M.; Bower, John F. published the artcile< Modular Access to Eight-Membered N-Heterocycles by Directed Carbonylative C-C Bond Activation of Aminocyclopropanes>, Recommanded Product: 5-Fluoroindole-2-carboxylic acid, the main research area is aminocyclopropane rhodium regioselective diastereoselective carbonylative heterocyclization; azocane preparation; C−C activation; azocanes; cyclopropanes; rhodium.

Aminocyclopropanes equipped with pendant nucleophiles undergo carbonylative heterocyclization triggered by C-C bond activation to generate eight-membered N-heterocycles, e.g., I. In these processes, intramol. “”capture”” of a rhodacyclopentanone intermediate by an aryl or N-based nucleophile is followed by C-C or C-N bond-forming “”collapse”” to the targets. These studies demonstrate how the combination of cyclopropane strain release and the templating effect of catalytically generated metallacycles can be harnessed to enable otherwise challenging medium ring closures.

Ye, Zenghui’s team published research in Organic Letters in 2019-12-20 | 399-76-8

Organic Letters published new progress about Aromatic carboxylic acids Role: RCT (Reactant), RACT (Reactant or Reagent). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Recommanded Product: 5-Fluoroindole-2-carboxylic acid.

Ye, Zenghui; Li, Yong; Xu, Kai; Chen, Na; Zhang, Fengzhi published the artcile< Cascade π-Extended Decarboxylative Annulation Involving Cyclic Diaryliodonium Salts: Site-Selective Synthesis of Phenanthridines and Benzocarbazoles via a Traceless Directing Group Strategy>, Recommanded Product: 5-Fluoroindole-2-carboxylic acid, the main research area is phenanthridine benzocarbazole preparation regioselective; indole carboxylic acid cyclic diaryliodonium salt decarboxylative annulation palladium.

A novel cascade π-extended decarboxylative annulation (PEDA) involved with cyclic diaryliodonium salts is described. Via fine-tuning of the reaction conditions, the Pd(II)-catalyzed site-selective N1/C2 or C2/C3 annulation of com. available indole-2-carboxylic acids can be achieved, affording valuable phenanthridines or benzocarbazoles, resp. The key strategy is the carboxylic acid functionality being employed as both a traceless directing group for the ortho C-N or C-C coupling and a reactive group for the cascade π-extended decarboxylative annulation in a highly step economical manner.

Kim, Weonjeong’s team published research in Chemical Science in 2021 | 4771-48-6

Chemical Science published new progress about Acylation catalysts (photochem.). 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Safety of 4-Methyl-1H-indole-3-carbaldehyde.

Kim, Weonjeong; Koo, Jangwoo; Lee, Hong Geun published the artcile< Benzylic C(sp3)-C(sp2) cross-coupling of indoles enabled by oxidative radical generation and nickel catalysis>, Safety of 4-Methyl-1H-indole-3-carbaldehyde, the main research area is benzylic indole preparation; indole aryl halide arylation cross coupling photocatalyst; acyl indole preparation; acid anhydride indole acylation cross coupling photocatalyst.

A mechanistically unique functionalization strategy for a benzylic C(sp3)-H bond was developed based on facile oxidation event of indole substrates. This novel pathway was initiated by efficient radical generation at benzylic position of substrate, with subsequent transition metal catalysis to complete overall transformation. Ultimately, an aryl or an acyl group could be effectively delivered from an aryl (pseudo)halide or an acid anhydride coupling partner, resp. The developed method utilized mild conditions and exhibited a wide substrate scope for both substituted indoles and C(sp2)-based reaction counterparts. Mechanistic studies showed that competitive hydrogen atom transfer (HAT) processes, which were frequently encountered in conventional methods, are not involved in the product formation process of the developed strategy.

Roca-Lopez, David’s team published research in Synlett in 2011-01-24 | 145513-91-3

Synlett published new progress about Alkenes, nitro Role: RCT (Reactant), RACT (Reactant or Reagent) (aryl-). 145513-91-3 belongs to class indole-building-block, and the molecular formula is C9H15NO2, HPLC of Formula: 145513-91-3.

Roca-Lopez, David; Merino, Pedro; Sayago, Francisco J.; Cativiela, Carlos; Herrera, Raquel P. published the artcile< Organocatalyzed Michael addition reaction by novel (2R,3aS,7aS)-octahydroindole-2-carboxylic acid, a new fused proline>, HPLC of Formula: 145513-91-3, the main research area is acetone nitroolefin Michael addition.

The authors present their results on the organocatalytic enantioselective Michael addition reaction of acetone to different nitroolefines using (2R,3aS,7aS)-octahydroindole-2-carboxylic acid [(R,S,S)-Oic] as a new and suitable catalyst. Computational calculations support the results obtained with (R,S,S)-Oic vs. its diastereomeric form (S,S,S)-Oic. The final products are obtained in good yields and moderate enantioselectivities (up to 58% ee).

Mehta, Ruhi’s team published research in ChemistrySelect in 2020-10-26 | 950846-89-6

ChemistrySelect published new progress about Absorption. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Reference of 950846-89-6.

Mehta, Ruhi; Luxami, Vijay published the artcile< A Novel ′On-Off′ Rhodamine Based Sensor for Colorimetric Detection of CN- and Its Application as Encoder-Decoder and Molecular Keypad Lock>, Reference of 950846-89-6, the main research area is rhodamine based sensor colorimetric detection mol keypad lock.

A novel rhodamine-phenalenedicarbonitrile based “”on-off”” sensor (Rho-Pdc) has been synthesized which is characterized by 1H NMR, 13C NMR and mass spectrometry. The photophys. studies of the dyad suggest its existence in spirolactam ring open form of rhodamine. ICT (Intramol. Charge Transfer) active sensor displays an absorption band at 577 nm with a shoulder at 520 nm and fluorescence band at 593 nm. The treatment of dyad Rho-Pdc with different anions shows its sensitivity and selectivity towards CN- ions in aqueous methanolic solution with lowest detection limit of 0.13 μM and the binding constant was determined to be 1.17 × 104 M-1 by applying Benesi-Hildebrand equation. The presence of CN- ions hinder the ICT process of dyad Rho-Pdc and shows a blue shift in absorption band of dyad Rho-Pdc with formation of new band at 488 nm as well as decrease in the intensity of emission band. Rho-Pdc has also been used for the colorimetric detection of CN- ions among different anions and concentrations The reversibility of Rho-Pdc.CN-complex has been achieved with Fe3+ ions which formed the basis for the construction of multiple mol. logic circuits.

ChemistrySelect published new progress about Absorption. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Reference of 950846-89-6.

Dawidowski, Maciej’s team published research in Journal of Medicinal Chemistry in 2020-01-23 | 93247-78-0

Journal of Medicinal Chemistry published new progress about Chagas disease. 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Safety of Methyl 1H-indole-7-carboxylate.

Dawidowski, Maciej; Kalel, Vishal C.; Napolitano, Valeria; Fino, Roberto; Schorpp, Kenji; Emmanouilidis, Leonidas; Lenhart, Dominik; Ostertag, Michael; Kaiser, Marcel; Kolonko, Marta; Tippler, Bettina; Schliebs, Wolfgang; Dubin, Grzegorz; Maeser, Pascal; Tetko, Igor V.; Hadian, Kamyar; Plettenburg, Oliver; Erdmann, Ralf; Sattler, Michael; Popowicz, Grzegorz M. published the artcile< Structure-Activity Relationship in Pyrazolo[4,3-c]pyridines, First Inhibitors of PEX14-PEX5 Protein-Protein Interaction with Trypanocidal Activity>, Safety of Methyl 1H-indole-7-carboxylate, the main research area is Trypanosoma infectious diseases PEX14 PEX5 PPI metabolic pathways MDS.

Trypanosoma protists are pathogens leading to a spectrum of devastating infectious diseases. The range of available chemotherapeutics against Trypanosoma is limited, and the existing therapies are partially ineffective and cause serious adverse effects. Formation of the PEX14-PEX5 complex is essential for protein import into the parasites’ glycosomes. This transport is critical for parasite metabolism and failure leads to mislocalization of glycosomal enzymes, with fatal consequences for the parasite. Hence, inhibiting the PEX14-PEX5 protein-protein interaction (PPI) is an attractive way to affect multiple metabolic pathways. Herein, we have used structure-guided computational screening and optimization to develop the first line of compounds that inhibit PEX14-PEX5 PPI. The optimization was driven by several X-ray structures, NMR binding data, and mol. dynamics simulations. Importantly, the developed compounds show significant cellular activity against Trypanosoma, including the human pathogen Trypanosoma brucei gambiense and Trypanosoma cruzi parasites.

Akins, Nicholas S’s team published research in ChemMedChem in 2022-04-05 | 399-76-8

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

Akins, Nicholas S.; Mishra, Nisha; Harris, Hannah M.; Dudhipala, Narendar; Kim, Seong Jong; Keasling, Adam W.; Majumdar, Soumyajit; Zjawiony, Jordan K.; Paris, Jason J.; Ashpole, Nicole M.; Le, Hoang V. published the artcile< C2-Salvinorin Ester 6,5-Fused Ring, Dual Kappa and Mu Opioid Receptor Agonists as Analgesics Devoid of Anxiogenic Effects>, Recommanded Product: 5-Fluoroindole-2-carboxylic acid, the main research area is methoxycarbonyl hydroxy dimethyl dioxobenzoisochromene aryl ester opioid receptor agonist.

Current common analgesics are mediated through the mu or kappa opioid receptor agonism. Unfortunately, selective mu or kappa receptor agonists often cause harmful side effects. However, ligands exhibiting dual agonism to the opioid receptors, such as to mu and kappa, or to mu and delta, have been suggested to temper undesirable adverse effects while retaining analgesic activity. Herein we report an introduction of various 6,5-fused rings to C2 of the salvinorin scaffold via an ester linker. In vitro studies showed that many of these compounds have dual agonism on kappa and mu opioid receptors. In vivo studies on the lead dual kappa and mu opioid receptor agonist demonstrated supraspinal thermal analgesic activity while avoiding anxiogenic effects in male mice, thus providing further strong evidence in support of the therapeutic advantages of dual opioid receptor agonists over selective opioid receptor agonists.

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

Cheng, Guangsheng’s team published research in European Journal of Organic Chemistry in 2017 | 4771-48-6

European Journal of Organic Chemistry published new progress about Allenes Role: RCT (Reactant), RACT (Reactant or Reagent). 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Product Details of C10H9NO.

Cheng, Guangsheng; Deng, Hongmei; He, Xiang; Gao, Yu; Li, Chunju; Jia, Xueshun; Li, Jian published the artcile< Isocyanide-Based Multicomponent Reaction To Furnish N-Functionalized Indoles by using N-Acyliminium Ions as Key Intermediates>, Product Details of C10H9NO, the main research area is indolyl pyrrolidinone preparation.

The present work discloses an efficient multicomponent reaction of isocyanides, allenoates, and indoles. This protocol provides rapid and direct access to N-functionalized indoles from readily available starting materials, in the absence of any catalyst. The strategy also features a broad substrate scope and mild conditions.

Xing, Fei’s team published research in Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy in 2020-08-15 | 950846-89-6

Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy published new progress about Autophagy. 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.

Xing, Fei; Zhang, Qilong; Gao, Lingfeng; Zheng, Gengxiu published the artcile< Fabrication of a fluorescent probe for in-situ and ratiometric visualization of autophagy>, Recommanded Product: 2-(2-Aminoethyl)-3′,6′-bis(diethylamino)spiro[isoindoline-1,9′-xanthen]-3-one, the main research area is fluorescent probe autophagy; Autophagy; Fluorescent probe; Ratiometric; pH sensitive.

In situ and real-time visualization of autophagy process is of vital importance for fundamental researches in biol. However, fluorescent probes for autophagy were rarely reported, which greatly hindered the study on autophagy. A fluorescent probe was rationally designed and fabricated for the ratiometric visualization of autophagy. The probe targeted non-lysosome organelles in healthy cells, and gave blue emission. During autophagy, the organelles together with the probe were delivered into acid lysosomes, and gave red fluorescence. In this way, the autophagy process could be monitored in ratiometric manner. The starvation induced autophagy was successfully visualized by the probe, and the inhibition effect of chloroquine to autophagy was also observed The authors expect that the probe can serve as powerful tool for the study of autophagy and relative areas.