399-76-8 | - Page 2 of 7 - Indole Building Blocks

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.

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

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.

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.

Wang, Limei’s team published research in Food Packaging and Shelf Life in 2021-09-30 | 399-76-8

Food Packaging and Shelf Life published new progress about Agaricus bernardii. 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Recommanded Product: 5-Fluoroindole-2-carboxylic acid.

Wang, Limei; Zhou, Yanfang; Wang, YangYang; Bu, Hongyu; Dong, Tungalag published the artcile< Changes in cell wall metabolism and flavor qualities of mushrooms (Agaricus bernardii) under EMAP treatments during storage>, Recommanded Product: 5-Fluoroindole-2-carboxylic acid, the main research area is Agaricus bernardii flavor cell wall metabolism EMAP storage.

To clarify the dynamic changes of cell wall metabolism and flavor components in Agaricus bernardii packed with the packaging materials during storage. The polyethylene (PE), poly (butylene adipate-co-terephthalate)/ poly (L-lactic acid) (ECFPLA) and PBAT/PLLA/ hydrophobic silica (ECFPLASiO2) with a different gas/water vapor permeability were used as equilibrium modified atm. packaging (EMAP) materials, and an appropriate gas concentration [O2 (0.01-0.03%), CO2 (4.58-6.62%)] was created inside the ECFPLASiO2 packaging, which led to Agaricus bernardii with higher level of cell wall components and lower level of cell wall degrading enzymes during the storage period. For the first time application of HS-SPME-GC-MS on an extract from fresh Agaricus bernardii. The results showed that volatile compounds of fresh Agaricus bernardii mainly consists of alcs., ketones and aldehydes, with 3-octanol, 3-octanone, 1-octene-3-alc. and phenylcarbinol being most abundant compounds During the storage time, the varieties and content of volatile compounds were changed in all treatments. Alcs., aldehydes, hydrocarbons and esters contents increased during the storage while ketones declined. Among all treatment groups, ECFPLASiO2 group showed higher most abundant compounds and organic acid content. The results suggest that ECFPLASiO2 film could be used to reduce the changes in cell walls and flavor components after harvest and extend the shelf life of Agaricus bernardii.

Liu, Boya’s team published research in ACS Applied Polymer Materials in 2022-09-09 | 399-76-8

ACS Applied Polymer Materials published new progress about Crosslinking. 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Safety of 5-Fluoroindole-2-carboxylic acid.

Liu, Boya; Liu, Yang; Liu, Xiangyang published the artcile< Enhanced Thermal Conductivity of All-Organic Aramid Nanofiber Films via Interfacial Coupling Reaction>, Safety of 5-Fluoroindole-2-carboxylic acid, the main research area is thermal conductivity organic aramid nanofiber film interfacial coupling.

It is still a great challenge to prepare intrinsically all-organic thermal conductive membrane with high in-plane and through-plane thermal conductivity Herein, we designed an all-organic aramid nanofiber thin film with in-plane and through-plane thermal conductivity as high as 15.7 and 0.26 W/mK, resp., through one step fluorination utilizing F2/N2. We proved that direct fluorination could induce the coupling reaction of benzene rings in neighboring aramid macromols. to form numerous covalent crosslinking bonds among aramid nanofibers. Benefiting from the crosslinking behavior, interfacial thermal resistance between the nanofibers was suppressed to some extent, thereby leading to enhancement of in-plane and through-plane thermal conductivity by 78.8% and 271.7%, resp., compared with the unmodified membranes. In addition, the thin films also possess high mech. strength and elec. insulation, which promote its application potential in flexible electronic fields.

Iioka, Ryoya’s team published research in European Journal of Organic Chemistry in 2021-03-08 | 399-76-8

European Journal of Organic Chemistry published new progress about Antitumor agents. 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Category: indole-building-block.

Iioka, Ryoya; Yorozu, Kohei; Sakai, Yoko; Kawai, Rika; Hatae, Noriyuki; Takashima, Katsuki; Tanabe, Genzoh; Wasada, Hiroaki; Yoshimatsu, Mitsuhiro published the artcile< Synthesis of azepino[1,2-a]indole-10-amines via [6+1] annulation of ynenitriles with Reformatsky reagent>, Category: indole-building-block, the main research area is azepinoindoleamine preparation annulation Lewis acid catalysis.

Lewis acid-catalyzed [6+1] annulation reactions of 2-cyano-1-propargyl- and 2-alkynyl-1-cyanomethyl-indoles with Reformatsky reagent are described. 8-Aryl, 8-alkyl-, 8-hetaryl-, 9-aryl, and 9-alkyl-azepino[1,2-a]indole amines were obtained through a 7-endo-mode cyclization of the β-aminoacrylate intermediates. The antiproliferative activity of the azepino[1,2-a]indoles analogs against the HCT-116 cells were also examined

Hrizi, Asma’s team published research in Molecules in 2021 | 399-76-8

Molecules published new progress about Alkenes 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, Reference of 399-76-8.

Hrizi, Asma; Cailler, Manon; Romdhani-Younes, Moufida; Carcenac, Yvan; Thibonnet, Jerome published the artcile< Synthesis of New Highly Functionalized 1H-Indole-2-carbonitriles via Cross-Coupling Reactions>, Reference of 399-76-8, the main research area is alkenyl indole carbonitrile preparation; aryl indole carbonirile preparation; 1H-indole-2-carbonitriles; Heck; Sonogashira; Stille; Suzuki–Miyaura.

An approach for the preparation of polysubstituted indole-2-carbonitriles through a cross-coupling reaction of compounds 1-(but-2-ynyl)-1H-indole-2-carbonitriles and 1-benzyl-3-iodo-1H-indole-2-carbonitriles was described. The reactivity of indole derivatives with iodine at position 3 was studied using cross-coupling reactions. The Sonogashira, Suzuki-Miyaura, Stille and Heck cross-couplings afforded a variety of di-, tri- and tetra-substituted indole-2-carbonitriles.

Schlegel, Marcel’s team published research in Journal of Organic Chemistry in 2019-05-03 | 399-76-8

Journal of Organic Chemistry published new progress about [4+2] Cycloaddition reaction. 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Quality Control of 399-76-8.

Schlegel, Marcel; Schneider, Christoph published the artcile< Iron(III)-Catalyzed (4 + 2)-Cycloannulation of 2-Hydroxy Ketoxime Ethers with Indol-2-ylamides: Synthesis of Indole-Fused 2-Piperidinones>, Quality Control of 399-76-8, the main research area is indole fused piperidinone diastereoselective preparation; hydroxy ketoxime ether indolecarboxamide cycloaddition iron catalyst.

A highly regio- and diastereoselective (4 + 2)-cycloannulation process of indanone-derived 2-hydroxy ketoxime ethers with 1,4-bisnucleophilic indol-2-ylamides has been developed. In the presence of 5 mol % FeCl3, densely functionalized 2-piperidinones containing two new σ-bonds and two vicinal quaternary stereogenic centers were formed under mild reaction conditions in a one-pot operation. Moreover, most of the products directly precipitated out of the solution and were isolated by simple filtration without purification by column chromatog.

Chen, Xiaoxue’s team published research in Bioorganic & Medicinal Chemistry in 2020-03-15 | 399-76-8

Bioorganic & Medicinal Chemistry published new progress about Covalent bond (SIRT2 covalent inhibitors). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Recommanded Product: 5-Fluoroindole-2-carboxylic acid.

Chen, Xiaoxue; Zou, Yefang; Wang, Jie; Cao, Zhuoxian; Liu, Jingzi; Li, Yan; Zhao, Yonglong; He, Bin published the artcile< Unexpected small molecules as novel SIRT2 suicide inhibitors>, Recommanded Product: 5-Fluoroindole-2-carboxylic acid, the main research area is sirtuin SIRT2 covalent inhibitors suicide inhibitors deacetylation deacylation; Covalent inhibitors; Deacetylation; Deacylation; SIRT2; Sirtuin; Suicide inhibitors.

A series of sirtuin inhibitor candidates were assembled based on an intermediate ester (1a) our accidently discovered. After screening and evaluation, several SIRT2 selective inhibitors were identified, which can inhibit all the deacetylation, defatty-acylation and debenzoylation of SIRT2. Among these inhibitors, compound 1e was the best SIRT2 selective inhibitors. The primary study on the inhibitory mechanism indicated that compound 1e may be a suicide inhibitor acting as an irreversible way. Given almost all reported sirtuin inhibitors are non-covalent, sirtuin covalent inhibitors are still need to be developed. These findings will facilitate for further development of SIRT2 selective and suicide inhibitors.

Tan, Yu Jia’s team published research in ACS Medicinal Chemistry Letters in 2021-05-13 | 399-76-8

ACS Medicinal Chemistry Letters published new progress about Amides, oxo Role: PAC (Pharmacological Activity), PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), THU (Therapeutic Use), BIOL (Biological Study), RACT (Reactant or Reagent), PREP (Preparation), USES (Uses). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Quality Control of 399-76-8.

Tan, Yu Jia; Li, Ming; Gunawan, Gregory Adrian; Nyantakyi, Samuel Agyei; Dick, Thomas; Go, Mei-Lin; Lam, Yulin published the artcile< Amide-Amine Replacement in Indole-2-carboxamides Yields Potent Mycobactericidal Agents with Improved Water Solubility>, Quality Control of 399-76-8, the main research area is methylamine carboxamide benzothiophene benzoselenophene preparation antimycobacterial lipophilicity.

Indolecarboxamides are potent but poorly soluble mycobactericidal agents. Here, it was found that modifying the incipient scaffold by amide-amine substitution and replacing the indole ring with benzothiophene or benzoselenophene led to striking (10-20-fold) improvements in solubility Potent activity could be achieved without the carboxamide linker but not in the absence of the indole ring. The indolylmethylamine, N-cyclooctyl-6-trifluoromethylindol-2-ylmethylamine (MIC90Mtb 0.13μM, MBC99.9Mtb 0.63μM), exemplifies a promising member that is more soluble and equipotent to its carboxamide equivalent It is also an inhibitor of the mycolate transporter MmpL3, a property shared by the methylamines of benzothiophene and benzoselenophene.