26/10/2022 - Indole Building Blocks

Ori, Mayuko et al. published their research in Tetrahedron in 2005 |CAS: 79815-20-6

The Article related to benzastatin e preparation, virantmycin preparation, tetrahydroquinoline preparation rearrangement indolinemethanol, indoline methanol preparation grignard addition acylindoline and other aspects.Recommanded Product: 79815-20-6

On February 21, 2005, Ori, Mayuko; Toda, Narihiro; Takami, Kazuko; Tago, Keiko; Kogen, Hiroshi published an article.Recommanded Product: 79815-20-6 The title of the article was Stereospecific synthesis of 2,2,3-trisubstituted tetrahydroquinolines: application to the total syntheses of benzastatin E and natural virantmycin. And the article contained the following:

An efficient methodol. for the synthesis of 2,2,3-trisubstituted tetrahydroquinolines has been developed, which involves the triphenylphosphine-CCl4-mediated stereospecific rearrangement of α,α-disubstituted indoline-2-methanols (I) to 2,2,3-trisubstituted tetrahydroquinolines. The rearrangement precursors I are readily prepared by the diastereoselective Grignard addition to 2-acylindolines. The total syntheses of (+)-benzastatin E (II) and natural virantmycin (III) were accomplished utilizing this methodol. This rearrangement reaction might afford some chem. precedent for the biogenetic pathway of the benzastatin family. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Recommanded Product: 79815-20-6

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

Wuertz, Sebastian et al. published their research in Angewandte Chemie, International Edition in 2008 |CAS: 65417-22-3

The Article related to aniline derivative acetoacetate condensation, enaminone aryl derivative preparation palladium catalyst oxidative cyclization, indole carboxylate derivative preparation kinetics and other aspects.Related Products of 65417-22-3

Wuertz, Sebastian; Rakshit, Souvik; Neumann, Julia J.; Droege, Thomas; Glorius, Frank published an article in 2008, the title of the article was Palladium-catalyzed oxidative cyclization of N-aryl enamines: from anilines to indoles.Related Products of 65417-22-3 And the article contains the following content:

The special advantage of the title reaction to form substituted indoles lies within the broad scope of the transformation: a multitude of N-aryl enaminones, e.g., I, can be prepared readily in one step from com. available anilines. Furthermore, anilines can be converted directly in a one-pot process into the indole products, e.g., II. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Related Products of 65417-22-3

Viswanathan, Rajesh et al. published their research in Journal of the American Chemical Society in 2003 |CAS: 79815-20-6

The Article related to ketimine preparation ketone addition arylamine, indoline derivative preparation radical based aryl amination cyclization ketimine, amino acid indolinecarboxylate asym preparation and other aspects.Computed Properties of 79815-20-6

On January 8, 2003, Viswanathan, Rajesh; Prabhakaran, Erode N.; Plotkin, Michael A.; Johnston, Jeffrey N. published an article.Computed Properties of 79815-20-6 The title of the article was Free Radical-Mediated Aryl Amination and Its Use in a Convergent [3 + 2] Strategy for Enantioselective Indoline α-Amino Acid Synthesis. And the article contained the following:

The scope of aryl radical additions to the nitrogen of azomethines is described. Aryl, trifluoromethyl alkyl, and α,β-unsaturated ketimines engage in regioselective aryl-nitrogen bond formation via 5-exo cyclizations of an aryl radical to azomethine nitrogen. Selectivity for carbon-nitrogen over carbon-carbon bond formation is generally high (>95:5) and competes only with direct aryl radical reduction by stannane (0-10%). α-Ketimines are a promising new class of carbon radical acceptors for which no competitive aryl radical reduction is observed The reaction conditions are pH-neutral and are therefore among the mildest methods available for amination of an aromatic ring. The ketimines examined did not suffer from competitive reduction by stannane, offering an advantage over the use of diazo and azide functional groups as nitrogen sources for carbon radicals. The free radical-mediated aryl amination was sequenced with the O’Donnell phase transfer-catalyzed enantioselective alkylation strategy of glycinyl imine to provide either enantiomer of indoline α-amino acids with high enantiomeric excess. These new constrained Ph alanine derivatives are now readily available for evaluation across a variety of applications. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Computed Properties of 79815-20-6

Zhang, Hongjun et al. published their research in Bioorganic Chemistry in 2022 |CAS: 79815-20-6

The Article related to bacillus escherichia esterase protein engineering enantioselectivity, (s)-indoline-2-carboxylic acid, biocatalysis, enantioselective, esterase, overexpression, protein engineering and other aspects.Formula: C9H9NO2

On March 31, 2022, Zhang, Hongjun; Cheng, Zeguang; Wei, Litian; Yu, Xinjun; Wang, Zhao; Zhang, Yinjun published an article.Formula: C9H9NO2 The title of the article was Semi-rational protein engineering of a novel esterase from Bacillus aryabhattai (BaCE) for resolution of (R,S)-ethyl indoline-2-carboxylate to prepare (S)-indoline-2-carboxylic acid. And the article contained the following:

A gene encoding an esterase from Bacillus aryabhattai (BaCE) was identified, synthesized and efficiently expressed in the Escherichia coli system. A semi-rational protein engineering was applied to further improve the enzymes enantioselectivity. Under the guidance of the mol. docking result, a single mutant BaCE-L86Q and a double mutant BaCE-L86Q/G284E were obtained, with its Emax value 6.4 times and 13.9 times of the wild-type BaCE, resp. The recombinant BaCEs were purified and characterized. The overwhelming E value demonstrated that BaCE-L86Q/G284E was a promising biocatalyst for the biol. resolution to prepare (S)-indoline-2-carboxylic acid. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Formula: C9H9NO2

Eklind, Karin Ingeborg et al. published their patent in 1995 |CAS: 130539-43-4

The Article related to fucosylated glycoside preparation bacterial adherence inhibitor, helicobacter pylori adhesion inhibitor fucosylated glycoside, gastric mucosa helicobacter pylori adhesion inhibitor and other aspects.Recommanded Product: 130539-43-4

On January 5, 1995, Eklind, Karin Ingeborg; Loenn, Hans Roland; Tiden, Anna-Karin Ulla Edit published a patent.Recommanded Product: 130539-43-4 The title of the patent was Preparation of fucosylated glycosides as inhibitors of bacterial adherence.. And the patent contained the following:

Guanidinyl Y-Z1-R, A-Z2-R, A-Z3-B-Z4-R, A-Z5-B-Z6-C-Z7-R, A-Z8-B-Z9-C-Z10-D-Z11-R, A-Z12-B-Z13-C-Z14-D-Z15-E-Z16-R [Z1-Z16 = O, S, CH2, NR25; R25 = H, alkyl, alkenyl, alkylcarbonyl, (substituted) PhCO; A = Q1; B = Q2; C = Q3; D = Q4; E = Q5; Y = Q6; R = H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylcarbonyl, alkenylcarbonyl, (substituted) cycloalkylalkylcarbonyl, arylcarbonyl, etc.; R1-R3 = H, halo, N3, guanidinyl, alkyl, alkenyl, alkynyl, (substituted) aryl, alkoxyalkyl, etc.; R1A-R4E = R1, YZ1; with provisos], were prepd for therapy or prophylaxis in conditions involving infection by Heliobacter pylori of human gastric mucosa. Thus, Et 3-O-(tri-O-benzyl-α-L-fucopyranosyl)-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside was stirred with N-iodosuccinimide, mol. sieves, and CF3CO2H in CH2Cl2/Et2O to give 97% Me 4,6-O-benzylidene-3-O-(tri-O-benzyl-α-fucopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranoside. This was refluxed 20 h with N2H4 in aqueous EtOH followed by acetylation of the crude product to give Me 2-acetamido-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside. The latter was hydrogenolyzed at 200 kPa over Pd/C in AcOH/EtOAc/H2O to give 90% Me 2-acetamido-2-deoxy-3-O-α-L-fucopyranosyl-D-glucopyranoside. Title compounds gave 34-93% inhibition of binding of Helicobacter pylori to human gastric tissue. Use of title compounds with various antibiotics, antacids, gastric secretion inhibitors, antigastritis drugs, and antiulcer drugs, is claimed. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Recommanded Product: 130539-43-4

Zoller, Jochen et al. published their research in Angewandte Chemie, International Edition in 2014 |CAS: 65417-22-3

The Article related to indole carboxylate preparation, enamine intramol oxidative cyclization palladium photoredox catalysis visible light, ch functionalization, heck reaction, photocatalysis, superoxide and other aspects.Related Products of 65417-22-3

Zoller, Jochen; Fabry, David C.; Ronge, Meria A.; Rueping, Magnus published an article in 2014, the title of the article was Synthesis of Indoles Using Visible Light: Photoredox Catalysis for Palladium-Catalyzed C-H Activation.Related Products of 65417-22-3 And the article contains the following content:

A combined palladium- and photoredox-catalyzed C-H olefination enables the synthesis of indoles. By using visible light, the direct C-H activation of aromatic enamines I (R1 = H, 4-PhO, 4-Cl, 2-F, 3,5-Me2, etc.; R2 = Me, Ph; R3 = Me, Et, t-Bu, PhCH2) can be achieved, and a variety of indoles II can be obtained in good yields under mild reaction conditions. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Related Products of 65417-22-3

Chisholm, Cora D. et al. published their research in Tetrahedron: Asymmetry in 2011 |CAS: 79815-20-6

The Article related to aromatic containing anion enantiomeric discrimination trimethylammonium modified cyclodextrin nmr, chiral nmr solvating agent trimethylammonium modified cyclodextrin anion substrate and other aspects.Related Products of 79815-20-6

On January 17, 2011, Chisholm, Cora D.; Wenzel, Thomas J. published an article.Related Products of 79815-20-6 The title of the article was Enantiomeric discrimination of aromatic-containing anionic substrates using cationic cyclodextrins. And the article contained the following:

Cationic α-, β-, and γ-cyclodextrins were prepared by reacting the corresponding native cyclodextrin (CD) with glycidyltrimethylammonium chloride (GTAC). The reaction conditions were varied to alter the degree of substitution of GTAC units on the cyclodextrin. The CD-GTAC derivatives, which retain a pos. charge independent of pH, were evaluated as water-soluble chiral NMR solvating agents for anionic substrates. The CD-GTAC derivatives are considerably more effective at causing enantiomeric discrimination in the 1H NMR spectra of aromatic-containing anionic substrates than the neutral native cyclodextrins. Derivatives with a degree of substitution of ∼1.5 were more effective than those with lower or higher degree of substitution. Not one of the α-, β-, and γ-CD-GTAC derivatives was consistently the most effective at causing enantiomeric discrimination for all of the substrates examined herein. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Related Products of 79815-20-6

Yamazaki, Kazuo et al. published their research in Journal of Organic Chemistry in 2003 |CAS: 65417-22-3

The Article related to indolecarboxylate solid phase preparation, fused pyridine pyridone solid phase preparation, solid phase preparation indolecarboxylate palladium rhodium catalyzed cyclization reaction and other aspects.Name: Methyl 2-methyl-1H-indole-3-carboxylate

On July 25, 2003, Yamazaki, Kazuo; Nakamura, Yosuke; Kondo, Yoshinori published an article.Name: Methyl 2-methyl-1H-indole-3-carboxylate The title of the article was Solid-Phase Synthesis of Indolecarboxylates Using Palladium-Catalyzed Reactions. And the article contained the following:

Indolecarboxylates are prepared on solid support using palladium-catalyzed reactions as the key steps. Supported β-amino-α,β-unsaturated esters are prepared either by attachment of tert-Bu acetoacetate to a resin followed by condensation with 2-haloanilines or by condensation of acryloyl chloride with a resin followed by Wacker-type oxidation of 2-haloanilines with the resin-bound acrylate in the presence of palladium catalysts. Supported α-amino-α,β-unsaturated esters are prepared by coupling of diethylphosphonoacetic acid to a resin followed by diazo transfer, rhodium-catalyzed insertion of 2-haloanilines, and base-mediated olefination with aldehydes. Palladium-catalyzed cyclization reactions of the α- or β-amino-α,β-unsaturated esters followed by cleavage of the resin-bound esters with sodium methoxide yields indolecarboxylates in moderate yields and purities. Rhodium-catalyzed insertion reactions of aminophenyl ketones and aldehydes with α-diazophosphonate esters followed by base-mediated cyclocondensation and cleavage from the resin with sodium methoxide also yields indolecarboxylates in low to moderate yields and purities. Resin-bound β-(halophenyl)-α-aminoacrylates are prepared either by attachment of an aminoacrylate to a resin followed by Heck arylation with an aryl halide or by rhodium-catalyzed insertion of an amine into a resin-bound α-diazophosphonate followed by olefination with halobenzaldehydes. Palladium-catalyzed cyclization of the resin-bound β-(halophenyl)-α-aminoacrylates followed by resin cleavage yields indolecarboxylates in 43-98% yields. A shorter version of this synthesis is also employed; palladium-catalyzed Heck reaction of 1,2-dihaloarenes with resin-bound acetylaminoacrylic acid followed by resin cleavage yields indolecarboxylates directly in 31-99% yields. Formylbromoarenes and -heteroarenes and methoxycarbonylarenes and -heteroarenes such as Me 2-bromobenzoate undergo palladium-catalyzed coupling with resin-bound acetylaminoacrylic acid followed by cyclization to yield fused pyridines and pyridones such as Me 1,2-dihydro-1-oxo-3-isoquinolinecarboxylate in 52-62% yields. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Name: Methyl 2-methyl-1H-indole-3-carboxylate

Prime, Michael et al. published their patent in 2012 |CAS: 879562-21-7

The Article related to piperidinyl acrylamide preparation transglutaminase tg2 inhibitor combination chemotherapy, neurodegenerative disorder huntington’s disease treatment piperidinyl acrylamide preparation and other aspects.Application In Synthesis of 1-(Cyclopropanecarbonyl)indoline-5-sulfonyl chloride

On November 29, 2012, Prime, Michael; Courtney, Stephen Martin; Marston, Richard; Dominguez, Celia; MacDonald, Douglas; Wityak, John published a patent.Application In Synthesis of 1-(Cyclopropanecarbonyl)indoline-5-sulfonyl chloride The title of the patent was Preparation of piperidin-4-yl substituted acrylamides as transglutaminase TG2 inhibitors. And the patent contained the following:

The title compounds I [A = (un)substituted (hetero)aryl, heterocycloalkyl; B = (un)substituted mono- or bicyclic heterocycloalkyl; R1 = H, NO2, COR (wherein R = H, alkyl, cycloalkyl, etc.), etc.; R2 = H or alkyl; R3-R5 = H, F, Cl, alkyl; p = 0-3; q = 0-1], were prepared E.g., a multi-step synthesis of the acrylamide II, starting from tert-Bu piperidin-4-ylcarbamate and 6-chloropyridine-3-sulfonyl chloride, was described. Exemplified compounds I were tested for human TG2 activity. Certain compounds I were found to have IC50 value less than 100 nM (no specific data given). Also provided are pharmaceutical compositions comprising at least one compound or pharmaceutically acceptable salt therein and one or more pharmaceutically acceptable vehicle. Methods of treating patients suffering from certain disease states responsive to the inhibition of transglutaminase TG2 activity are described. These disease states include neurodegenerative disorders such as Huntington’s disease. Also described are methods of treatment which include administering at least one compound or pharmaceutically acceptable salt thereof as a single active agent or administering at least one compound or pharmaceutically acceptable salt thereof in combination with one or more other therapeutic agents. The experimental process involved the reaction of 1-(Cyclopropanecarbonyl)indoline-5-sulfonyl chloride(cas: 879562-21-7).Application In Synthesis of 1-(Cyclopropanecarbonyl)indoline-5-sulfonyl chloride

Rios, Ramon et al. published their research in Advanced Synthesis & Catalysis in 2007 |CAS: 79815-20-6

The Article related to chiral amine catalyzed enantioselective cyclopropanation alpha beta unsaturated aldehyde, alpha beta unsaturated aldehyde cyclopropanation bromomalonate bromoacetoacetate ester catalyst and other aspects.Application of 79815-20-6

On May 31, 2007, Rios, Ramon; Sunden, Henrik; Vesely, Jan; Zhao, Gui-Ling; Dziedzic, Pawel; Cordova, Armando published an article.Application of 79815-20-6 The title of the article was A simple organocatalytic enantioselective cyclopropanation of α,β-unsaturated aldehydes. And the article contained the following:

A highly chemo- and enantioselective organocatalytic cyclopropanation of α,β-unsaturated aldehydes with bromomalonate and 2-bromoacetoacetate esters is presented. The reaction is catalyzed by chiral amines and gives access to 2-formylcyclopropanes in high yields and up to 99% ee. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Application of 79815-20-6