56895-60-4

Usage

Derivative of indole

A modified version of the heterocyclic aromatic compound found in plants.

Sedative effects

Known for its calming and sleep-inducing properties.

Natural occurrence

Found in certain alcoholic beverages, such as wine and beer.

Precursor to serotonin

Plays a key role in mood, appetite, and sleep regulation.

Potential applications

Medicine and neuroscience due to its effects on the central nervous system.

Upstream product

• 75-21-8 oxirane 
• 21909-49-9 ethyl (2-methylindol-3-yl)acetate 
• 1487-15-6 2-Methyl-4,5-dihydrofuran 
• 59-88-1 phenylhydrazine hydrochloride 
• 1912-43-2 2-methyl-3-indoleacetic acid 
• 22980-10-5 (2-methyl-3-indolyl)glyoxyloyl chloride 
• 95-20-5 2-methyl-1H-indole 
• 62995-59-9 (2-methyl-1H-indol-3-yl)oxoacetic acid methyl ester 
• 5390-04-5 pent-1-yn-5-ol 
• 226065-37-8 N-phenyl-hydrazine carboxylic acid tert-butyl ester 
• 10229-10-4 pent-3-yn-1-ol 
• 100-63-0 phenylhydrazine 
• 5416-80-8 2-methyl-1H-indole-3-carbaldehyde 
• 1071-73-4 5-Hydroxy-2-pentanone 

Downstream Products

• 83087-79-0 N,O-dibenzyl-2-methyltryptophol 
• 404950-80-7 panobinostat 

Relevant academic research and scientific papers

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

PROCESS FOR THE PREPARATION OF PANOBINOSTAT

The present invention relates to a new process for the preparation of Panobinostat and intermediates thereof.

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.

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.

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

Mechanistic dichotomy with alkynes in the formal hydrohydrazination/Fischer indolization tandem reaction catalyzed by a Ph3PAuNTf 2/pTSA binary system

An efficient method involving a formal hydrohydrazination/Fischer indolization tandem reaction to synthesize 2,3-disubstituted indoles from alkynes and arylhydrazines has been developed. The approach uses a Ph 3PAuNTf2/pTSA·H2O binary catalytic system in which a very low catalyst loading of Ph3PAuNTf2 (2 mol-%) is required. The reaction time is very short and, most importantly, the reaction is not sensitive to moisture. The mechanism of these reactions has been investigated and the results led us to propose an interesting mechanistic dichotomy. When alkynes have OH/COOH groups in the tether, hydroalkoxylation/ hydrocarboxylation occurred to generate exocyclic enol ethers/lactones that reacted with hydrazines to produce indoles. In cases where the alkynes lack OH/COOH groups, hydration occurs to generate ketones that react with arylhydrazines to give the desired indoles. A method for the synthesis of 2,3-disubstituted indoles from alkynes and arylhydrazines is reported that utilizes a Ph3PAuNTf2/pTSA·H2O binary catalytic system. Mechanistic aspects including an alkyne-dependant dichotomy is also discussed. Copyright

Zinc-promoted hydrohydrazination of terminal alkynes: An efficient domino synthesis of indoles

(Chemical Equation Presented) Indole click chemistry: The quest for better catalysts for the intermolecular hydrohydrazination to indoles leads to zinc salts. A simple one-pot synthesis forms indoles from arylhydrazines and terminal alkynes. The pharmacologically relevant indole building blocks are selectively formed in the presence of zinc triflate (Zn(OTf)2) or ZnCl 2 (see scheme).

A General Synthesis of Substituted Indoles from Cyclic Enol Ethers and Enol Lactones

(Equation presented) A general method was developed for the one-pot synthesis of highly functionalized indoles from simple, commercially available aryl hydrazines and cyclic enol ethers. Enol lactones were also used as substrates, affording substituted indole acetic acid or indole propionic acid derivatives. This procedure affords 2,3-disubstituted indoles as single regioisomers from the appropriately substituted enol ether or enol lactone. This method was highlighted in the efficient synthesis of the antimigraine drug sumitriptan and the antiinflammatory drug indomethacin.