16078-35-6

Usage

Uses

Used in Chemical Synthesis:
1 5-Diacetylindoline 97 is used as a reactant for α-arylation reactions, which are important in the synthesis of various organic compounds and pharmaceuticals. Its reactivity and structural properties make it a valuable component in this process.
Used in Pharmaceutical Industry:
1 5-Diacetylindoline 97 is used as a reactant for the preparation of 5-HT1B receptor antagonists. These compounds have potential applications in the treatment of various neurological and psychiatric disorders, such as migraine, depression, and anxiety.
Used in KCNQ2 Opener Agents:
1 5-Diacetylindoline 97 is used as a reactant for the synthesis of N-(1-benzo[1,3]dioxol-5-yl)ethyl-, N-[1-(2,3-dihydro-benzofuran-5-yl)ethyl-, and N-[1-(2,3-dihydro-1H-indol-5-yl)ethylacrylamides. These compounds act as KCNQ2 opener agents, which have potential therapeutic applications in the treatment of conditions like epilepsy and certain types of arrhythmias.
Used in Neurobiology Research:
1 5-Diacetylindoline 97 is used as a reactant for the preparation of 1-acyl-7-nitroindolines, which serve as L-glutamate photoreleasing agents in cerebellar granule neurons. These agents are essential tools in neurobiological research, helping scientists study the role of L-glutamate in neuronal signaling and synaptic plasticity.

InChI:InChI=1/C12H13NO2/c1-8(14)10-3-4-12-11(7-10)5-6-13(12)9(2)15/h3-4,7H,5-6H2,1-2H3

Upstream product

• 16078-30-1 1-Acetyl-2,3-dihydro-1H-indole 
• 75-36-5 acetyl chloride 
• 67-64-1 acetone 
• 496-15-1 1-indoline 

Downstream Products

• 67932-65-4 5-ethyl-2,3-dihydro-1H-indole 
• 16078-34-5 5-Acetyl-2,3-dihydro-1H-indole 
• 1213251-54-7 C₁₈H₁₆FNO₂ 
• 1337532-08-7 5-{1-[(2,5-difluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}furo[2,3-d]pyrimidin-4-amine 
• 53330-94-2 1-(1H-indol-5-yl)ethanone 
• 765945-13-9 N-[1-(2,3-dihydro-1H-indol-5-yl)-ethyl]-3-(2-fluoro-phenyl)-acrylamide 
• 4770-32-5 1-(5-hydroxy-2,3-dihydroindol-1-yl)ethanone 
• 239135-34-3 methyl 1-[S-(4-amino-4-carboxybutanoyl)]-7-nitroindoline-5-acetate 

Relevant academic research and scientific papers

Indoleline compounds and derivatives thereof, preparation methods, pharmaceutical compositions and applications

The present invention discloses a class of indoleline compounds and derivatives thereof, preparation methods, pharmaceutical compositions and applications. The structure of such indoleline compounds is as follows formula (I), the derivatives thereof relate to stereoisomers of the indole compound, tautomers, metabolites, metabolic precursors, prodrugs, solvates, salts of solvates, crystals, pharmaceutically acceptable salts or mixtures thereof. This class of indoleline compounds and their derivatives has a significant inhibitory effect on the activity of indoleamine 2,3-bioxygenase 1, can be used to prepare drugs for the treatment of indoleamine 2,3-bioxygenase-mediated immunosuppression-related diseases, by activating the host immune response to exert antitumor activity.

Acetylation of N-heteroaryl bromides via PdCl2/(o-tolyl) 3P catalyzed heck reactions

A new user-friendly and convenient method for the acetylation of N-heteroaryl bromides is described. This process is based on the palladium-catalyzed olefination of an N-heteroaryl bromide with butyl vinyl ether, followed by acid hydrolysis of the intermediate heteroaryl vinyl ether in situ. Isopropanol at 85°C, in the presence of K3PO 4·3H2O (2 equiv), PdCl2 (2 mol%) and (o-tolyl)3P (4 mol%), provided the best conditions, giving yields of N-heteroaryl bromides up to 75%. Georg Thieme Verlag Stuttgart.

Identification of a potent and selective 5-HT1B receptor antagonist

An SAR study around the mixed 5-HT1ABD receptor antagonist SB-272183 found that introduction of cis-2,6-dimethyl substitution onto the piperazine ring was a key structural change, which imparted a combination of both excellent selectivity over

Synthesis and KCNQ2 opener activity of N-(1-benzo[1,3]dioxol-5-yl-ethyl, N-[1-(2,3-dihydro-benzofuran-5-yl)-ethyl, and N-[1-(2,3-dihydro-1H-indol-5-yl)- ethyl acrylamides

Bioisosteric replacement studies led to the identification of N-(1-benzo[1,3]dioxol-5-yl-ethyl)-3-(2-chloro-phenyl)-acrylamide ((S)-3) as a highly potent KCNQ2 opener, and 3-(2,6-difluoro-phenyl)-N-[1-(2,3-dihydro- benzofuran-5-yl)-ethyl]-acrylamide ((S)-4), and N-[1-(2,3-dihydro-1H-indol-5-yl) -ethyl]-3-(2-fluoro-phenyl)-acrylamide ((S)-5) as highly efficacious KCNQ2 openers. In contrast, their respective R enantiomers showed significantly less or no appreciable KCNQ2 opener activity even at the highest concentration tested (10μM). Because of its high potency and moderate efficacy as well as its convenient synthesis, (±)-3 was selected as a reference compound for analyzing efficacies of KCNQ openers in electrophysiology studies. Compounds (S)-4 and (S)-5 demonstrated significant activity in reducing neuronal hyperexcitability in rat hippocampal slices. The synthesis and the KCNQ2 opener activity of these acrylamides are described.

THE SYNTHESIS OF 5- and 7-ACETYLINDOLE DERIVATIVES. I. THE PHOTOCHEMICAL REARRANGEMENT OF 1-ACETYLINDOLINE

5- and 7-Acetyl substituted indole derivatives have been prepared via intramolecular photo rearrangement of acyl radical and intramolecular electrophilic acylation of 1-acetylindoline.

Synthese d'(indolyl-3)-4 dihydro-2,5 furanonnes-2 hydrosolubles

Une cyclisation du type Dieckmann suivie d'une decarboxylation permet d'acceder directement aux (indolyl-3)-4 dihydro-2,5 furanonnes-2 acetylees ou non sur l'homocycle a partir des ethoxycarbonylacetoxyacetyl-3 indoles correspondants sans protection prealable de la position 1 du cycle indolique et du substituant acyle de l'homocycle.