16077-10-4

Usage

Molecular Class

Indole derivatives

Biological Activities

Anti-inflammatory, antioxidant, and neuroprotective effects

Potential Applications

Organic synthesis, medicinal chemistry, and development of new drugs for neurological disorders

Common Use

Intermediate for the synthesis of pharmaceutical compounds

Upstream product

• 39755-95-8 5-methoxyisatine 
• 100-39-0 benzyl bromide 
• 104-94-9 4-methoxy-aniline 
• 100-44-7 benzyl chloride 
• 1426840-39-2 C₁₆H₁₆BrNO₂ 

Downstream Products

• 65836-82-0 1-benzyl-2,3-dihydro-5-methoxy-1H-indol-2-one 
• 865479-32-9 N-benzyl-5-hydroxyisatin 
• 1190109-65-9 (R)-1-benzyl-3-hydroxy-5-methoxy-3-(2-methylbut-3-en-2-yl)indolin-2-one 
• 1190109-49-9 (S)-3-allyl-1-benzyl-3-hydroxy-5-methoxyindolin-2-one 
• 1190109-57-9 (S)-1-benzyl-3-((R)-but-3-en-2-yl)-3-hydroxy-5-methoxyindolin-2-one 
• 1206485-38-2 methyl (2E)-(1-benzyl-5-methoxy-2-oxo-1,2-dihydro-3H-indol-3-ylidene)ethanoate 
• 1229649-03-9 3-allyl-1-benzyl-3-hydroxy-5-methoxy-2-oxo-2,3-dihydroindole 
• 1243238-28-9 (3R)-1-benzyl-3-hydroxy-5-methoxy-3-[(1S,2E)-1-phenylpent-2-enyl]indolin-2-one 
• 1246886-63-4 C₁₉H₁₇NO₄ 
• 1267807-82-8 diethyl {[(3E)-1-benzyl-5-methoxy-2-oxoindolin-3-ylidene]methyl}phophonate 
• 1345838-27-8 (2'R,3'R)-ethyl 1-benzyl-5-methoxy-2-oxospiro[indoline-3,2'-oxirane]-3'-carboxylate 
• 1345838-28-9 (2'S,3'R)-ethyl 1-benzyl-5-methoxy-2-oxospiro[indoline-3,2'-oxirane]-3'-carboxylate 
• 1449481-87-1 benzyl-5-methoxy-4'-methylspiro[indoline-3,2'-pyran]-2,6'(3'H)-dione 
• 1424357-99-2 (R)-1-benzyl-3-hydroxy-5-methoxy-3-(propa-1,2-dien-1-yl)indolin-2-one 

Relevant academic research and scientific papers

Dynamic Kinetic Asymmetric Transformation of Racemic Diastereomers: Diastereo- and Enantioconvergent Michael–Henry Reactions to Afford Spirooxindoles Bearing Furan-Fused Rings

Dynamic kinetic asymmetric transformation (DYKAT) reactions of racemic diastereomer mixtures that afford the products as essentially single diastereomers with high enantioselectivities are described. We demonstrated the DYKAT in the diastereo- and enantio

Applications of Ytterbium(II) Reagent as Grignard Reagent and Single-Electron Transfer Reagent in the Synthesis of 3-Substituted 2-Oxindoles

The use of ytterbium(II) reagent as both nucleophilic reagent and single-electron transfer reagent in the reaction of isatin derivatives with ytterbium(II) reagent is reported. From a synthetic point of view, a general, efficient, and experimentally simple one-pot method for the preparation of 3-substituted 2-oxindoles was developed.

Organocatalytic Enantioselective Synthesis of Tetrahydro-Furanyl Spirooxindoles via [3+2] Annulations of 3-Hydroxyoxindoles and Cyclic Ketolactams

Asymmetric construction of pharmacologically interesting tetrahydrofuranyl spirooxindole frameworks has been achieved through organocatalytic [3+2] annulations of the readily available 3-hydroxyoxindoles and pyrrolidone-derived cyclic ketolactams. A variety of chiral spiro tetrahydrofuranyl products, which contain four contiguous stereocenters including two tetrasubstituted carbon centers, have been rapidly synthesized with remarkable results (up to 99% yield, >95:5 dr, and 99:1 er). Synthetic derivatization of the hemiketal moiety enables the installation of various halogen atoms into the structurally complex molecules in a stereospecific manner. Preliminary screening of anticancer bioactivity was performed, and 4 w showed obvious inhibitory capacity to the proliferation on a panel of cancer cell lines. (Figure presented.).

Carbene-Catalyzed Enantioselective Aromatic N-Nucleophilic Addition of Heteroarenes to Ketones

The aromatic nitrogen atoms of heteroarylaldehydes are activated by carbene catalysts to react with ketone electrophiles. Multi-functionalized cyclic N,O-acetal products are afforded in good to excellent yields and optical purities. Our reaction involves the formation of an unprecedented aza-fulvene-type acylazolium intermediate. A broad range of N-heteroaromatic aldehydes and electron-deficient ketone substrates works effectively in this transformation. Several of the chiral N,O-acetal products afforded through this protocol exhibit excellent antibacterial activities against Ralstonia solanacearum (Rs) and are valuable in the development of novel agrichemicals for plant protection.

Reductive aromatization of oxindoles to 3-substituted indoles

A practical and scalable approach for the synthesis of 3-substituted indoles is delineated via hydride nucleophilic addition to 3-substituted-2-oxindoles. The reaction proceeds through reductive aromatization involving indolinium ion intermediate. A wide range of 3-functionalized indoles have been synthesized. The method is employed for the synthesis of 3,3?-bis-indoles and a dimeric 3-indole derivative. Moreover, this protocol is used to obtain naturally occuring amino acid tryptamine.

Candida antarctica lipase-B-catalyzed kinetic resolution of 1,3-dialkyl-3-hydroxymethyl oxindoles

Candida antarctica (CAL-B) lipase-catalyzed resolution of 1,3-dialkyl-3-hydroxymethyl oxindoles has been performed to obtain (R)-1,3-dialkyl-3-acetoxymethyl oxindoles with up to 99% ee and (S)-1,3-dialkyl-3-hydroxymethyl oxindoles with up to 78% ee using vinyl acetate as acylating agent and acetonitrile as solvent transforming (S)-3-allyl-3-hydroxymethyl oxindole to (3S)-1′-benzyl-5-(iodomethyl)-4,5-dihydro-2H-spiro[furan-3,3′-indolin]-2′-one. The optically active 3-substituted-3-hydroxymethyl oxindoles and spiro-oxindoles are among the key synthons in the synthesis of potentially biologically active molecules.

Synthesis and anticancer activity evaluation of azepinobisindoles;the isomeric iheyamine A-derivatives

Azepinobisindole derivatives, the isomeric Iheyamine skeleton, were prepared and their anticancer activity evaluation were investigated against two human cancer cell lines, Hepatocellular carcinoma (HepG2) and human cervical cancer line (HeLa) as well as the normal cell line (Vero cell line) using MTT assay. The anticancer activity results indicated that 2-methoxy-5-methyl-5H-azepino[2,3-b:4,5-b]diindole was the most active derivative against tested cell lines. Additionally, molecular docking study in silico the possible inhibitory effect of cyclin-dependent kinase 2 (CDK2) by the azepinoindole revealed that all synthesized compounds fit well in the binding cavity of CDK2.

Synthetic method of isatin derivative

The invention provides a synthetic method of an isatin derivative. The method comprises the following steps of: taking an N-alkyl-N-aryl glycine ester derivative as a substrate in an organic solvent and under oxygen gas, and performing cyclization reactio

Asymmetric Conjugate Addition of Ethylene Sulfonyl Fluorides to 3-Amido-2-oxindoles: Synthesis of Chiral Spirocyclic Oxindole Sultams

An enantioselective conjugate addition of ethylene sulfonyl fluorides to 3-amido-2-oxindoles has been developed. Quinine-derived squaramides were identified as efficient catalysts. A series of spirocyclic oxindole sultams were prepared with excellent yields and enantioselectivities. A reaction mechanism via bifunctional activation was proposed.

NHC-Catalyzed Aldol-Like Reactions of Allenoates with Isatins: Regiospecific Syntheses of γ-Functionalized Allenoates

An N-heterocyclic carbene (NHC) catalyzed γ-specific aldol-like reaction between allenoates and isatins has been achieved under mild conditions, giving trisubstituted allene derivatives bearing isatin moiety in moderate to good yields with high diastereoselectivity and excellent atom efficiency. The DFT computations indicated that the formation of the γ-adduct was more energetically favorable than that of the α-adduct. The result reported herein opens a new route for NHC-promoted allenoate-involved reaction.