62995-59-9

Usage

InChI:InChI=1/C12H11NO3/c1-7-10(11(14)12(15)16-2)8-5-3-4-6-9(8)13-7/h3-6,13H,1-2H3

Upstream product

• 67-56-1 methanol 
• 95-20-5 2-methyl-1H-indole 
• 527-31-1 hexaketocyclohexane 
• 22980-10-5 (2-methyl-3-indolyl)glyoxyloyl chloride 
• 79-37-8 oxalyl dichloride 

Downstream Products

• 1032339-96-0 methyl 2-(2-methyl-1-(phenylsulfonyl)-1H-indol-3-yl)-2-oxoacetate 
• 56895-60-4 2-(2-methyl-1H-indol-3-yl)ethanol 
• 6628-34-8 ethyl 2-(2-methyl-1H-indol-3-yl)-2-oxoacetate 
• 52915-55-6 2-(1-benzyl-2-methyl-1H-3-indolyl)-1-ethanol 
• 863889-88-7 N-benzyl-3-(2-{tert-butyldimethylsilyloxy}ethyl)-2-methyl-1H-indole 
• 1375277-47-6 (2S)-N-(benzo[d][1,3]dioxol-5-yl)-2-(2-(1-ethyl-2-methyl-1H-indol-3-yl)-2-hydroxyacetamido)-N-methyl-3-phenylpropanamide 
• 1375277-44-3 (S)-N-(benzo[d][1,3]dioxol-5-yl)-2-(2-(1-ethyl-2-methyl-1H-indol-3-yl)-2-oxoacetamido)-N-methyl-3-phenylpropanamide 

Relevant academic research and scientific papers

Carbene-Catalyzed Construction of Carbazoles from Enals and 2-Methyl-3-oxoacetate Indoles

Direct and rapid construction of carbazoles has been successfully developed via carbene-catalyzed oxidative formal [4 + 2] annulation of enals with 2-methyl-3-oxoacetate indoles. This metal-free reaction features a broad substrate scope, features good functional-group tolerance, proceeds under mild conditions, and can be easily scaled up.

Copper-catalyzed carbonylative transformations of indoles with hexaketocyclohexane

With hexaketocyclohexane octahydrate as the carbon monoxide source, a novel procedure for copper-catalyzed direct double carbonylation of indoles has been established. Using alcohols as reaction partners, moderate to good yields of the desired double carbonylation products have been obtained. Wide functional group tolerance and substrate scope can be observed.

An environmentally friendly protocol for oxidative halocyclization of tryptamine and tryptophol derivatives

An environmentally friendly and efficient protocol (KX/oxone) for oxidative halocyclization of tryptamine/tryptophol derivatives was developed and demonstrated with 28 examples and concise total synthesis of cyclotryptamine alkaloid protubonines A and B. The distinct advantage of this protocol over all previous methods is that no organic byproduct is generated from a halogenating agent or oxidant, thus greatly reducing the environmental impact of halocyclization and facilitating the post-reaction purification.

Processing 2-Methyl- l -Tryptophan through Tandem Transamination and Selective Oxygenation Initiates Indole Ring Expansion in the Biosynthesis of Thiostrepton

Thiostrepton (TSR), an archetypal member of the family of ribosomally synthesized and post-translationally modified thiopeptide antibiotics, possesses a biologically important quinaldic acid (QA) moiety within the side-ring system of its characteristic thiopeptide framework. QA is derived from an independent l-Trp residue; however, its associated transformation process remains poorly understood. We here report that during the formation of QA, the key expansion of an indole to a quinoline relies on the activities of the pyridoxal-5′-phosphate-dependent protein TsrA and the flavoprotein TsrE. These proteins act in tandem to process the precursor 2-methyl- l-Trp through reversible transamination and selective oxygenation, thereby initiating a highly reactive rearrangement in which selective C2-N1 bond cleavage via hydrolysis for indole ring-opening is closely coupled with C2′-N1 bond formation via condensation for recyclization and ring expansion in the production of a quinoline ketone intermediate. This indole ring-expansion mechanism is unusual, and represents a new strategy found in nature for l-Trp-based functionalization.

Dearomatization of tryptophols via a vanadium-catalyzed asymmetric epoxidation and ring-opening cascade

An enantioselective epoxidation of tryptophols followed by an intramolecular epoxide opening reaction was realized by chiral vanadium catalysts derived from C2 symmetric bis-hydroxamic acid (BHA) ligands. 3a-Hydroxyfuroindoline derivatives with up to 89% yield and 90% ee were obtained under mild reaction conditions.

Spiropyran photoswitches in the context of DNA: Synthesis and photochromic properties

A new design is presented for the incorporation of spiropyran photoswitches into nucleic acids by oligonucleotide solid phase synthesis. This design enables interaction of the 6-nitrospirobenzopyran (NitroBIPS) photoswitch with the adjacent nucleobases and leaves the photochemical properties of NitroBIPS intact. UV/Vis spectroscopy and HPLC revealed that NitroBIPS incorporated into DNA consists of up to 40 % merocyanine in its thermal equilibrium and undergoes reversible switching between the photoisomeric spiropyran (SP) and merocyanin (MC) state by alternating excitation using visible light or heat for at least fifteen switching cycles. Exchanging the chromene part of NitroBIPS on the DNA level gives access to differently substituted spiropyran derivatives allowing the screening for spiropyrans with suitable properties in a straightforward manner. Thus, by incorporating the highly hydrolysis-stable pyrido-spiropyran derivative PyBIPS pure light-triggered reversible switching of a spiropyran in DNA has been realized for the first time. Therefore, this design represents a new useful platform for investigating the photochromic behavior of different spiropyran photoswitches in a nucleic acid environment and for using spiropyrans to induce light- or heat-triggered changes in conformations or in fluorescence quenching properties of oligonucleotides. Yes, it does switch! With a new design strategy the photochemical properties of spiropyran photoswitches can be retained in DNA. Spiropyrans can be diversified on the DNA level enabling screening for spiropyrans with suitable properties in a straightforward manner (see scheme). By incorporating the highly stable spiropyran derivative PyBIPS, pure light-triggered reversible switching of a spiropyran in DNA has been realized for the first time. Copyright

Copper(I)-catalyzed cascade dearomatization of 2-substituted tryptophols with arylidonium salts

Copper(I)-catalyzed dearomative arylation and vinylation of 2-substituted tryptophols were realized with a subsequent cyclization reaction. The cascade dearomatization sequence provided versatile furoindoline derivatives with two quaternary carbon centers

FAAH INHIBITORS

The present disclosure relates to compounds useful as inhibitors of the enzyme Fatty Acid Amide Hydrolase (FAAH). The disclosure also provides pharmaceutically acceptable compositions comprising the compounds of the disclosure and methods of using the com

NOVEL ANTIVIRAL COMPOUNDS

The present invention relates to a compound of formula I: or a pharmaceutically acceptable salt thereof, wherein the symbols are as defined in the specification; a pharmaceutical composition comprising the same, a method for treating or preventing a viral infection such as HIV using the same.

Synthesis of substituted carbazoles via electrocyclization of in situ generated enamines from 1-phenylsulfonyl-2/(3)-methyl-3/(2)-vinylindoles and DMF·DMA/DMA·DMA

Interaction of 2/(3)-methyl-3/(2)-vinylindoles and DMF·DMA/DMA·DMA at 110 °C led to the in situ generation of enamines, which on concurrent electrocyclization followed by subsequent aromatization afforded substituted carbazoles.