Tag: M.W=150-200

Zhao, Yin; Li, Hongfang; Yin, Shan; Wu, Yandan; Ni, Guanghui published the artcile< Visible-Light-Promoted Indole C-3 Formylation Using Eosin Y as a Photoredox Catalyst>, SDS of cas: 4771-48-6, the main research area is formyl indole preparation green chem; indole formylation eosin Y visible light.

A visible-light-mediated C-3 formylation of indole catalyzed by eosin Y has been developed using tetramethylethylenediamine as a carbon source and air as an oxidant. This protocol shows high tolerance to a large quantity of functional groups under mild conditions and provides 3-formylated indoles with good yields. This method is a highly attractive alternative to the approach of traditional formylation.

Synlett published new progress about Formylation. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, SDS of cas: 4771-48-6.

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

Zhou, Xiao-Yu; Chen, Xia; Liu, Hai-Long published the artcile< KI catalyzed C-H functionalization of acetone for the synthesis of 2-oxopropyl hetero-aromatic carboxylates>, Category: indole-building-block, the main research area is heteroaryl carboxylic acid acetone potassium iodide catalyst bond activation; oxopropyl heteroarylcarboxylate preparation.

KI catalyzed C-H functionalization of acetone with hetero-aromatic carboxylic acids was developed. With potassium iodide as catalyst and sodium chlorite as oxidant, cascade reaction including α-H electrophilic substitution of acetone and nucleophilic substitution of iodoacetone occurred smoothly. 2-Oxopropyl hetero-aromatic carboxylates were obtained with the good to excellent yields.

Synthetic Communications published new progress about Aromatic carboxylic acids Role: RCT (Reactant), RACT (Reactant or Reagent) (hetero). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Category: indole-building-block.

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

Bai, Jian-Fei; Zhao, Lulu; Wang, Fang; Yan, Fachao; Kano, Taichi; Maruoka, Keiji; Li, Yuehui published the artcile< Organocatalytic Formal (3+2) Cycloaddition toward Chiral Pyrrolo[1,2-a]indoles via Dynamic Kinetic Resolution of Allene Intermediates>, Recommanded Product: 4-Methyl-1H-indole-3-carbaldehyde, the main research area is indole propargylic alc preparation phosphoric acid enantioselective regioselective cycloaddition; pyrroloindole preparation.

The chiral phosphoric acid catalyzed formal (3+2) cycloaddition of 3-substituted 1H-indoles and propargylic alcs. containing a functional directing group (p-NHAc or p-OH) was reported. A straightforward method to synthesize chiral pyrrolo[1,2-a]indole bearing a tetrasubstituted carbon stereocenter was represented. The reaction proceeded smoothly with a wide array of substrate tolerance to deliver various chiral pyrrolo[1,2-a]indoles in up to 93% yield and 98% ee. The utility of this method is highlighted by the diverse transformations of the products into various indole derivatives

Organic Letters published new progress about [3+2] Cycloaddition reaction catalysts (regioselective, stereoselective). 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Recommanded Product: 4-Methyl-1H-indole-3-carbaldehyde.

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

Qin, Hui; Li, Qi; Xu, Jian; Zhang, Jie; Qu, Wei; Liu, Wenyuan; Feng, Feng; Sun, Haopeng published the artcile< A Mild and Direct C(sp3)-S Cross-Coupling of Oxindoles with Thiols: Synthesis of Unsymmetrical 3-Thiooxindoles>, Application In Synthesis of 20870-77-3, the main research area is thiooxindole preparation coupling oxindole thiol.

Herein, an operationally simple and mild strategy to construct sulfenation of oxindoles with a series of thiols in the absence of transition metals was developed. This methodol. provides an efficient way to directly form a C-S bond at the C-3 position of oxindoles under mild reaction conditions with a cheap and common solvent and base in moderate to good yields.

Journal of Organic Chemistry published new progress about Cross-coupling reaction. 20870-77-3 belongs to class indole-building-block, and the molecular formula is C8H6ClNO, Application In Synthesis of 20870-77-3.

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

Cadelis, Melissa M.; Pike, Elliot I. W.; Kang, Weirong; Wu, Zimei; Bourguet-Kondracki, Marie-Lise; Blanchet, Marine; Vidal, Nicolas; Brunel, Jean Michel; Copp, Brent R. published the artcile< Exploration of the antibiotic potentiating activity of indolglyoxylpolyamines>, Quality Control of 93247-78-0, the main research area is bis indolyloxoacetamidopropyl butane diaminium trifluoroacetate preparation; antibacterial antifungal activity cytotoxicity SAR; Antimicrobial; Indole; Indolglyoxylamide; Polyamine; Potentiation.

A series of substituted di-indolglyoxylamido-spermine analogs I [R1 = 7-Me, 5-F, 5,6-di-Br, etc.] were prepared and evaluated for intrinsic antimicrobial properties and the ability to enhance antibiotic action. As a compound class, intrinsic activity was typically observed towards Gram-pos. bacteria and the fungus Cryptococcus neoformans, with notable exceptions being the compounds I [R1 = 5-Br, 5-Cl] analogs which also exhibited modest activity (MIC 34-50 μM) towards the Gram-neg. bacteria Escherichia coli and Klebsiella pneumoniae. Several analogs enhanced the activity of doxycycline towards the Gram-neg. bacteria Pseudomonas aeruginosa, E. coli, K. pneumoniae and Acinetobacter baumannii. Of particular note was the identification of five antibiotic enhancing analogs I [R1 = 5-Br, 7-F, 7-Me] which also exhibited low to no cytotoxicity and red blood cell haemolytic properties. The mechanisms of action of the I [R1 = 5-Br, 7-F] analogs were attributed to the ability to disrupt the integrity and depolarize, bacterial membranes.

European Journal of Medicinal Chemistry published new progress about Amines Role: ADV (Adverse Effect, Including Toxicity), PAC (Pharmacological Activity), RCT (Reactant), SPN (Synthetic Preparation), THU (Therapeutic Use), BIOL (Biological Study), RACT (Reactant or Reagent), PREP (Preparation), USES (Uses). 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Quality Control of 93247-78-0.

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

Ding, Lu; Gao, Run-Duo; You, Shu-Li published the artcile< Palladium(0)-Catalyzed Intermolecular Asymmetric Cascade Dearomatization Reaction of Indoles with Propargyl Carbonate>, Safety of 5-Fluoroindole-2-carboxylic acid, the main research area is alkylindolyl methyl malonate preparation propargyl carbonate palladium tandem dearomatization; alkyl methylene dihydrocarbazole dicarboxylate chemoselective regioselective enantioselective preparation; allylic compounds; asymmetric catalysis; cascade reactions; dearomatization; palladium.

An intermol. asym. cascade dearomatization reaction of indole derivatives with propargyl carbonate was developed. The challenges associated with both the chemoselectivity between the carbon and nitrogen nucleophile and the enantioselective control during the formation of an all-carbon quaternary stereogenic center were well addressed by a Pd catalytic system derived from the Feringa ligand. A series of enantioenriched multiply substituted fused indolenines were provided in good yields (71-86%) with excellent enantioselectivity (91-96% ee) and chemoselectivity (3/4>19:1 in most cases).

Chemistry – A European Journal published new progress about Acid chlorides Role: RCT (Reactant), RACT (Reactant or Reagent). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Safety of 5-Fluoroindole-2-carboxylic acid.

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

Kalir, Asher; Balderman, D. published the artcile< Improved synthesis of some fluoroindoles>, Product Details of C9H6FNO2, the main research area is fluoroindoles; indoles fluoro.

2,5-F2-C6-H3NO2 (109 g.) was treated with 155 g. NCCH2CO2Et and 31.6 g. Na in 1000 ml. EtOH for 2 hrs. to give 26% 4-fluoroanthro-xanonitrile, m. 70-1°. 2,4-(O2N)FC6H3Me (155 g.) was refluxed 14 hrs. with 196 g. N-bromosuccinimide in 600 ml. CCl4 and 2 g. benzoyl peroxide and treated directly with pyridine to give 198 g. I (X = 4-F), m. 201-2°, and 37 g. 2,4-(O2N)FC6H3-CHBr2, m. 63-4°. I (X = 5-F and 6-F), m. 189-90°, and 202-4°, resp., were similarly obtained in 64 and 71% yield. I (X = 4-F) was treated with 150 g. p-ONC6H4NMe2.HCl in 1 l. EtOH and 720 ml. 2.5N NaOH at <5° for 1 hr., and then treated with 1.5 l. 6N H2SO4 to give 86 g. 2-O2N X C6H3CHO (II) (where X = 4-F), m. 32-3°, via III (X = 4-F), m. 165-6°. The following compounds were similarly prepared (X, % yield II, m.p. II, % yield III, and m.p. III given): 5-F, 86, 94-5°, 92, 155-6°; 6-F, 95, 62-3°, 96, 151-2°. II (X = 6-F) was treated with MeNO2 to give 76% 2,4-F(O2N)C6H3CH:CHNO2, m. 84°, which was catalytically reduced to 34-63% 4-fluoroindole, m. 29-30°, accompanied by IV, m. 200° (decomposition). The method of K. and S. Szara (1963) was used to prepare V (R, % yield, and m.p. given): CHO, 73, 190-1°; CH:CMeNO2, 81, 191-2°; CH2CHMeNH2, 64, 103-5° (HCl salt m. 240-1°, picrate m. 222-3°). 6-Fluoro-3-(2-nitrovinyl)indole, m. 190-2°, and 6-fluorotryptamine m. 83-4°, were similarly prepared in 68 and 51% yield, resp. V (R = CHO) (3.5 g.) was treated with 6 g. KMnO4 in 120 ml. Me2CO at <40° to give 47% V (R = CO2H), m. 273° (decomposition). 5-Fluoro-3-indolecarboxylic acid, m. 234-6° (decomposition), and 6-fluoro-3-indolecarboxylic acid, m. 242-4° (decomposition), were similarly prepared in 54 and 48% yield, resp. V (R = CH2CHMeNH2) was less active than the 5-fluoro derivative, but more active than the 6-fluoro derivative in the activity cage test on mice. Israel Journal of Chemistry published new progress about 23077-43-2. 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Product Details of C9H6FNO2.

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; 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.

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.

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

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.

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.

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

Kilic-Kurt, Zuehal; Acar, Cemre; Ergul, Mustafa; Bakar-Ates, Filiz; Altuntas, Tunca G. published the artcile< Novel indole hydrazide derivatives: Synthesis and their antiproliferative activities through inducing apoptosis and DNA damage>, Recommanded Product: 5-Fluoroindole-2-carboxylic acid, the main research area is anticancer activity apoptosis cell cycle DNA damage Bax Bcl2; DNA damage; anticancer activity; apoptosis; cell cycle; synthesis.

A series of novel indole hydrazide derivatives was synthesized and evaluated for their anticancer activities. Compound 12(I) exhibited the highest antiproliferative activity against the MCF-7 cell line, with an IC50 value of 3.01μM. Treatment of MCF-7 cells with compound 12 led to cell cycle arrest at the G0/G1 phase and also displayed a significant annexin V binding pattern, indicating that compound 12 is effective in apoptotic cell death. The Western blot anal. showed that compound 12 increased the expression of proapoptotic Bax and decreased the levels of the antiapoptotic Bcl-2 protein. It was also observed that MCF-7 cells treated with compound 12 showed reduced levels of procaspase-3 and -9 proteins. Moreover, compound 12 treatment induced a significant DNA damage in MCF-7 cells by increasing H2AX and ATM phosphorylation.

Archiv der Pharmazie (Weinheim, Germany) published new progress about Annexin V Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Recommanded Product: 5-Fluoroindole-2-carboxylic acid.

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